Document:

Exhibit 10.1

 

EXECUTION COPY

 

SECURITIES PURCHASE AGREEMENT

 

This Securities Purchase
Agreement (this “Agreement”) is entered into as of the 14th day of August, 2015, by and among
Tempus Applied Solutions Holdings, Inc., a Delaware corporation (the “Company”), and the investors signatory
hereto and set forth on Exhibit A hereto (each, in its capacity as an investor hereunder, and not in any other capacity,
an “Investor” and, collectively, the “Investors”), with reference to the following
facts:

 

A.          The Company and the Investors are executing and delivering this Agreement in reliance upon the exemptions from securities registration
afforded by Section 4(a)(2) of the Securities Act of 1933, as amended (the “1933 Act”), and Rule 506(b)
of Regulation D as promulgated by the United States Securities and Exchange Commission (the “SEC”) under
the 1933 Act.

 

B.           On July 31, 2015 (the “Business Combination Date”), the Company and the other parties thereto, including
Chart Acquisition Corp., a Delaware corporation (“Chart”), Tempus Applied Solutions, LLC, a Delaware
limited liability company (“Tempus”), consummated the transaction contemplated by that certain Agreement
and Plan of Merger, dated as of January 5, 2015 (as amended, including by the First Amendment to Agreement and Plan of Merger,
dated as of March 20, 2015, the Second Amendment to Agreement and Plan of Merger, dated as of June 10, 2015 and the Third Amendment
to Agreement and Plan of Merger, dated as of July 15, 2015, the “Merger Agreement” and such transactions,
the “Business Combination”). In connection with the Merger Agreement, the Company prepared and filed
with the SEC a Registration Statement on Form S-4 (333-201424), which became effective on July 17, 2015 (as amended or supplemented,
the “Registration Statement”).

 

C.           Prior to the consummation of the Business Combination, the Company authorized a new series of convertible preferred stock of the
Company designated as Series A Convertible Preferred Stock, $0.0001 par value per share (together with any non-voting preferred
shares issued in replacement thereof in accordance with the terms thereof, the “Preferred Stock”), the
terms of which are set forth in the certificate of designations for such series of Preferred Stock (the “Certificate
of Designations”) that was filed with the Delaware Secretary of State on July 30, 2015 along with an amendment and
restatement of the Company’s certificate of incorporation (the “Amended Charter”), which Preferred
Stock is convertible into shares of the Company’s common stock, $0.0001 par value per share (the “Common Stock”)
(such shares of Common Stock issuable pursuant to the terms of the Certificate of Designations, including, without limitation,
upon conversion or otherwise, collectively, the “Conversion Shares”), in accordance with the terms of
the Certificate of Designations.

 

D.          The Company is a party to that certain Registration Rights Agreement, dated as of December 13, 2012 (as amended, including by
the First Amendment to Registration Rights Agreement, dated as of June 20, 2015, and the Second Amendment to Registration Rights
Agreement, dated as of July 31, 2015, the “Founders Registration Rights Agreement”), together with Chart,
each of the Investors, and certain other persons or entities named as Holders therein (together with the Investors, the “Holders”).

 

E.          The Investors wish to purchase from the Company, and the Company wishes to sell to the Investors, on the date of this Agreement,
upon the terms and conditions set forth in this Agreement, (i) an aggregate of Two Hundred Fifty Thousand (250,000) shares of
Common Stock (the “Common Shares”), (ii) warrants in the form attached hereto as Exhibit B (the
“Series A-3 Warrants”) to acquire an aggregate of One Hundred Eighty-Seven Thousand Five Hundred (187,500)
shares of Common Stock or Preferred Stock (as exercised, collectively, the “Series A-3 Warrant Shares”)
and (iii) warrants in the form attached hereto as Exhibit C (the “Series B-3 Warrants” and together
with the Series A-3 Warrants, the “Warrants” and, collectively with the Common Stock, the “Purchased
Securities”) to acquire an aggregate of Sixty-Two Thousand Five Hundred (62,500) shares of Common Stock or Preferred
Stock (as exercised, collectively, the “Series B-3 Warrant Shares”, and together with the Series A-3
Warrant Shares, the “Warrant Shares” and, collectively with any Conversion Shares, the “Underlying
Securities”) in exchange for an aggregate purchase price of One Million U.S. Dollars ($1,000,000) (the “Aggregate
Purchase Price”), with each Investor paying the portion of the Aggregate Purchase Price and receiving the portion
of the Purchased Securities set forth next to such Investor’s name on Exhibit A hereto (such purchase and sale of
the Purchased Securities is referred to herein as the “Securities Purchase”).

 

    	 

    	 

    

 

F.          Capitalized terms used but not otherwise defined herein shall have the meanings set forth in the Merger Agreement.

 

NOW, THEREFORE, in
consideration of the foregoing premises and the mutual covenants hereinafter contained, the parties hereto agree as follows:

 

1.             Purchase of Purchased Securities. Upon the terms and subject to the conditions set forth herein, on the date hereof,
the Company shall issue and sell to each Investor, and each Investor shall purchase from the Company, the Purchased Securities
set forth next to such Investor’s name on Exhibit A hereto (with respect to each Investor, the “Investor’s
Purchased Securities”) or the portion of the Aggregate Purchase Price set forth next to such Investor’s name
on Exhibit A hereto (with respect to each Investor, the “Investor’s Purchase Price”). Each of
the Purchased Securities shall be issued with applicable restrictive legends for unregistered securities.

 

2.             Closing. The consummation of the Securities Purchase (the “Closing”) will take place on the
date of this Agreement immediately after the execution hereof at offices of Ellenoff, Grossman & Schole LLP, 1345 Avenue of
the Americas, New York, NY 10105. By mutual agreement of the parties the Closing may take place by conference call and facsimile
(or other electronic transmission of signature pages). At the Closing:

 

(a)        each Investor shall deliver or cause to be delivered to the Company:

 

(i)         such Investor’s Purchase Price by wire transfer of immediately available funds to an account designated by the Company;
and

 

(ii)        a copy of the Third Amendment to Registration Rights Agreement in the form attached hereto as Exhibit D (the “Founders
RRA Amendment”), duly executed by such Investor;

 

(b)         the Company shall:

 

(i)         instruct its transfer agent to credit each Investor with the Common Shares portion of such Investor’s Purchased Securities
on the Company’s books and records and, if and as requested by such Investor, to promptly (A) deliver stock certificates
for such Investor’s Common Shares to such Investor to the address set forth underneath such Investor’s name on the
signature pages hereto or (B) subject to applicable securities laws and to the extent applicable, deliver the Common Shares to
the balance account of the broker of such Investor set forth underneath such Investor’s name on the signature pages hereto
(the “Investor Broker”), at the Depository Trust Company in accordance with instructions
delivered by the Investor Broker to the Company;

 

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(ii)        issue to each Investor a Series A-3 Warrant and a Series B-3 Warrant for the portion of such Investor’s Purchased Securities
(and promptly thereafter deliver original signed copies of such Investor’s Warrants to such Investor to the address set
forth underneath such Investor’s name on the signature pages hereto);

 

(iii)       deliver to each Investor a copy of the Founders RRA Amendment, duly executed by the Company, Chart and Holders, including the
Investors, of at least 66-2/3% of the Registrable Securities (as defined in the Founders Registration Rights Agreement) as of
immediately prior to the Closing;

 

(iv)       deliver to each Investor a written consent and waiver, in form and substance reasonably acceptable to the Company and the Investors,
from each New Investor consenting to the terms and conditions of this Agreement and the other Purchase Documents and the consummation
by the Company of the transactions contemplated hereby and thereby, and waiving, with respect to this Agreement and the other
Purchase Documents and the transactions contemplated hereby and thereby such New Investor’s rights under (and any failure
of the Company to comply with the notice, timing and other requirements of), (A) Section 14 of such New Investor’s New Investor
Purchase Agreement, (B) Sections 2(b), 2(f) and 17 of such New Investors’ Pubco Series A-1 Warrant, (C) Sections 2(b) and
2(f) of such New Investors’ Pubco Series B-1 Warrant and (D) with respect to the issuance of Purchased Warrants and any
Preferred Stock upon exercise of the Purchased Warrants, Section 13 of the Certificate of Designations with respect to such New
Investor’s Preferred Stock; and

 

(v)        deliver to each Investor a written consent and waiver, in form and substance reasonably acceptable to the Company and the Investors,
from the Company Insider Investor consenting to the terms and conditions of this Agreement and the other Purchase Documents and
the consummation by the Company of the transactions contemplated hereby and thereby, and waiving, with respect to this Agreement
and the other Purchase Documents and the transactions contemplated hereby and thereby the Company Insider Investor’s rights
under (and any failure of the Company to comply with the notice, timing and other requirements of), (A) Section 16(m) of the Company
Insider Investor’s Insider Purchase Agreement, (B) Sections 2(b), 2(f) and 17 of the Company Insider Investor’s Pubco
Series A-2 Warrant and (C) Sections 2(b) and 2(f) of the Company Insider Investor’s Pubco Series B-2 Warrant; and

 

(c)         the parties hereto shall execute and/or deliver such other documents and agreements as are customary and reasonably necessary
to effectuate the Securities Purchase.

 

3.            Representations and Warranties of the Company. The Company represents and warrants to each Investor, as of the date
hereof, that:

 

(a)         Organization and Qualification. The Company and each of its subsidiaries (each, a “Company Subsidiary”)
are duly incorporated or otherwise organized, validly existing and in good standing under the laws of the jurisdiction of its
incorporation or organization (as applicable), with the full corporate power and authority to own and use its properties and assets
and to carry on its business as currently conducted. Neither the Company nor any Company Subsidiary is in violation of any of
the provisions of its respective certificate or articles of incorporation, bylaws or other organizational or charter documents,
except, with respect to the Company Subsidiaries, for violations which would not, individually or in the aggregate, have or reasonably
be expected to result in a Material Adverse Effect. The Company and each Company Subsidiary are duly qualified to conduct its
respective businesses and are in good standing as a foreign corporation or other entity in each jurisdiction in which the nature
of the business conducted or property owned by it makes such qualification necessary, except where the failure to be so qualified
or in good standing, as the case may be, would not, individually or in the aggregate, have or reasonably be expected to result
in a Material Adverse Effect.

 

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(b)         Authorization and Binding Obligation. The Company has the requisite power and authority to enter into and perform its obligations
under this Agreement and each of the other agreements and documents to which it is a party or otherwise bound in connection with
the transactions contemplated by this Agreement, including the Investor Warrants and the Founders RRA Amendment (collectively,
the “Purchase Documents”), and to issue the Purchased Securities in accordance with the terms hereof
and thereof. The execution and delivery of the Purchase Documents by the Company and the consummation by the Company of the transactions
contemplated hereby and thereby, including, without limitation, the issuance of the Purchased Securities, have been duly authorized
by board of directors of the Company and, other than (i) such filings required under applicable securities or “Blue Sky”
laws of the states of the United States and (ii) such consents described on Schedule 3(c)(ii) attached hereto, no further
filing, consent, or authorization is required by the Company or of its board of directors or its stockholders. This Agreement
and the other Purchase Documents to which it is a party have been duly executed and delivered by the Company and constitute the
legal, valid and binding obligations of the Company enforceable against the Company in accordance with their respective terms,
except as such enforceability may be limited by general principles of equity or applicable bankruptcy, insolvency, reorganization,
moratorium, liquidation or similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights
and remedies.

 

(c)         No
Conflict; Required Filings and Consents.

 

(i)         The execution, delivery and performance of the Purchase Documents by the Company and the consummation by the Company of the transactions
contemplated hereby and thereby (including, without limitation, the issuance of the Purchased Securities) will not (A) result
in a violation of the Amended Charter, the Certificate of Designations or bylaws of the Company, the terms of any equity instrument
of the Company or any of the Company Subsidiaries or any of the organizational documents of any of the Company Subsidiaries, (B)
conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a default) under,
or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture or instrument
to which the Company or any of the Company Subsidiaries is a party or otherwise bound, or (C) result in a violation of any law,
rule, regulation, order, judgment or decree (including U.S. federal and state securities laws, rules, and regulations) or the
rules and regulations of the OTCQB (the “Principal Market”), in each case, applicable to the Company
or any of its Subsidiaries or by which any property or asset of the Company or any of the Company Subsidiaries is bound or affected.

 

(ii)        Except as required under applicable securities or “Blue Sky” laws of the states of the United States, and as described
on Schedule 3(c)(ii), neither the Company nor any of its Subsidiaries is required to obtain any consent, authorization
or order of, or, make any filing or registration with, any court, governmental agency or any regulatory or self-regulatory agency
or any other Person in order for it to execute, deliver or perform any of its obligations under or contemplated by the Purchase
Documents, in each case in accordance with the terms hereof or thereof. All consents, authorizations, orders, filings and registrations
(which the Company is required to obtain pursuant to the preceding sentence) have been obtained or effected (except for those
required to be obtained or effected after the Closing, which will be obtained or effected within the time periods prescribed by
applicable law), and the Company and the Company Subsidiaries are unaware of any facts or circumstances that might prevent the
Company from obtaining or effecting any of the registration, application or filings pursuant to the preceding sentence. The Company
is not in violation of the listing requirements of the Principal Market and has no knowledge of any facts that would reasonably
lead to delisting or suspension of the shares of Common Stock by the Principal Market in the foreseeable future.

 

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(d)        Issuance of the Purchased Securities. The issuance of the Purchased Securities is duly authorized. Upon issuance in accordance
with the terms of the Purchase Documents, the Warrants shall be validly issued, fully paid and non-assessable and free from all
taxes, liens, charges and other encumbrances with respect to the issue thereof. Upon issuance in accordance with the terms of
the Purchase Documents, the Common Shares will be validly issued, fully paid and non-assessable and free from all preemptive or
similar rights, taxes, liens, charges and other encumbrances with respect to the issue thereof, with the holders being entitled
to all rights accorded to a holder of Common Stock. Upon issuance in accordance with the Warrants, the Underlying Securities will
be validly issued, fully paid and non-assessable and free from all preemptive or similar rights, taxes, liens, charges and other
encumbrances with respect to the issue thereof (other than those that may be imposed by applicable securities laws), with the
holders being entitled to all rights accorded to a holder of Common Stock (or Preferred Stock with respect to the exercise of
Warrants to purchase Preferred Stock in accordance with the terms thereof).

 

(e)        Registration Statement. At the time the Registration Statement and any amendments thereto became effective and as of the
Business Combination Date, the Registration Statement and any amendments thereto complied in all material respects with the requirements
of the 1933 Act, the Exchange Act of 1934, as amended (the “Exchange Act”), and the rules and regulations
of the SEC promulgated thereunder and all other applicable laws and regulations and did not contain any untrue statement of a
material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein not
misleading.

 

(f)         No Consideration Paid. No commission, broker’s fee or other remuneration has been paid by the Company for soliciting
the sale of the Purchased Securities as contemplated by this Agreement and the other Purchase Documents.

 

4.            Representations and Warranties of the Investors. Each Investor, severally and not jointly, hereby represents and warrants
to the Company as of the date hereof, as follows:

 

(a)         Organization and Authority. Such Investor has the requisite power and authority to enter into and perform its obligations
under this Agreement and each of the other Purchase Documents to which it is a party or otherwise bound. If such Investor is not
a natural person, the execution and delivery by such Investor of this Agreement and each of the other Purchase Documents to which
it is a party or otherwise bound and the consummation by such Investor of the transactions contemplated hereby and thereby have
been duly authorized by such Investor’s board of directors or other governing body.

 

(b)         Reliance on Exemptions. Such Investor understands that the Purchased Securities are being offered and sold in reliance
on specific exemptions from the registration requirements of United States federal and state securities laws and that the Company
is relying in part upon the truth and accuracy of, and such Investor’s compliance with, the representations, warranties,
agreements, acknowledgments and understandings of such Investor set forth herein and in the other Purchase Documents to which
such Purchaser is a party or otherwise bound in order to determine the availability of such exemptions and the eligibility of
such Investor to acquire such Investor’s Purchased Securities. Each Investor understands that the Purchased Securities being
purchased hereunder have not been registered under the 1933 Act, nor qualified under any foreign or state securities laws, and
that they are being offered and sold pursuant to an exemption from such registration and qualification based in part upon the
representations of such Investor contained herein. Such Investor is acquiring such Investor’s Purchased Securities hereunder
for its own account for investment and not with a view towards the resale, transfer or distribution thereof, nor with any present
intention of distributing such Investor’s Purchased Securities, in each case in violation of the 1933 Act. Such Investor
has not agreed to give any Person any interest or right in such Investor’s Purchased Securities.

 

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(c)         Validity; Enforcement. This Agreement and the other Purchase Documents to which the Investor is a party have been duly
and validly authorized, executed and delivered on behalf of such Investor and shall constitute the legal, valid and binding obligations
of such Investor enforceable against such Investor in accordance with their respective terms, except as such enforceability may
be limited by general principles of equity or to applicable bankruptcy, insolvency, reorganization, moratorium, liquidation and
other similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights and remedies.

 

(d)        No Conflicts. The execution, delivery and performance by such Investor of this Agreement and the other Purchase Documents
to which such Investor is a party or otherwise bound, and the consummation by such Investor of the transactions contemplated hereby
and thereby will not (i), if such Investor is not a natural person, result in a violation of the organizational documents of such
Investor or (ii) conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a
default) under, or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture
or instrument to which such Investor is a party or otherwise bound, or (iii) result in a violation of any law, rule, regulation,
order, judgment or decree (including federal and state securities laws) applicable to such Investor, except in the case of clauses
(ii) and (iii) above, for such conflicts, defaults, rights or violations which would not, individually or in the aggregate, reasonably
be expected to have a material adverse effect on the ability of such Investor to perform its obligations hereunder or under the
other Purchase Documents to which such Investor is a party or otherwise bound.

 

5.            Reservation of Shares; Listing. 

 

(a)        Reservation of Shares. So long as any of the Warrants remain outstanding, the Company shall take all action necessary to
at all times have authorized, and reserved for the purpose of issuance, no less than 150% of the maximum number of Warrant Shares
issuable upon exercise of all the Warrants then outstanding (without regard to any limitations on the exercise of the Warrants
set forth therein) (collectively, the “Required Reserve Amount”); provided, that at no time shall
the number of shares of Common Stock reserved pursuant to this Section 5(a) be reduced other than proportionally in connection
with any exercise and/or redemption of Warrants. If at any time the number of shares of Common Stock authorized and reserved for
issuance is not sufficient to meet the Required Reserved Amount, the Company will promptly take all corporate action necessary
to authorize and reserve a sufficient number of shares, including, without limitation, calling a special meeting of stockholders
to authorize additional shares to meet the Company’s obligations pursuant to the Purchase Documents, in the case of an insufficient
number of authorized shares, obtain stockholder approval of an increase in such authorized number of shares, and use its reasonable
best efforts to cause the holders of the management shares of the Company to vote in favor of an increase in the authorized shares
of the Company to ensure that the number of authorized shares is sufficient to meet the Required Reserved Amount.

 

(b)        Listing. After the Closing, (x) the Company shall maintain the Common Stock’s authorization for quotation on the
Principal Market or secure its listing on The New York Stock Exchange, the NYSE MKT, the Nasdaq Capital Market, the Nasdaq Global
Market or the Nasdaq Global Select Market (each, an “Eligible Market”) and (y) neither the Company nor
any of the Company Subsidiaries shall take any action which could be reasonably expected to result in the deauthorization, delisting
or suspension of the Common Stock on an Eligible Market on which the Common Stock is quoted or listed. The Company shall pay all
fees and expenses in connection with satisfying its obligations under this Section 5.

 

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6.            Form D and Blue Sky. The Company shall make all filings and reports relating to the Securities Purchase required under
applicable securities or “Blue Sky” laws of the states of the United States following the date hereof, if any, and
comply with all applicable foreign, federal, state and local laws, statutes, rules, regulations and the like relating to the Securities
Purchase. Each Investor shall reasonably cooperate with the Company in connection with the foregoing and promptly provide any
information reasonably requested by the Company in connection with any such filing or report.

 

7.            Miscellaneous. 

 

(a)         Governing Law; Jurisdiction; Jury Trial. All questions concerning the construction, validity, enforcement and interpretation
of this Agreement shall be governed by the internal laws of the State of New York, without giving effect to any choice of law
or conflict of law provision or rule (whether of the State of New York or any other jurisdictions) that would cause the application
of the laws of any jurisdictions other than the State of New York. Each party hereby irrevocably submits to the exclusive jurisdiction
of the state and federal courts sitting in The City of New York, Borough of Manhattan for the adjudication of any dispute hereunder
or in connection herewith or with any transaction contemplated hereby or discussed herein, and hereby irrevocably waives, and
agrees not to assert in any suit, action or proceeding, any claim that it is not personally subject to the jurisdiction of any
such court, that such suit, action or proceeding is brought in an inconvenient forum or that the venue of such suit, action or
proceeding is improper. Each party hereby irrevocably waives personal service of process and consents to process being served
in any such suit, action or proceeding by mailing a copy thereof to such party at the address for such notices to it under this
Agreement and agrees that such service shall constitute good and sufficient service of process and notice thereof. Nothing contained
herein shall be deemed to limit in any way any right to serve process in any manner permitted by law. EACH PARTY HEREBY IRREVOCABLY
WAIVES ANY RIGHT IT MAY HAVE, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER OR IN CONNECTION
WITH OR ARISING OUT OF THIS AGREEMENT OR ANY TRANSACTION CONTEMPLATED HEREBY.

 

(b)        Headings. The headings of this Agreement are for convenience of reference and shall not form part of, or affect the interpretation
of, this Agreement. The words “including,” “includes,” “included” and “include,”
when used, are deemed to be followed by the words “without limitation.” Whenever the context may require, (i) any
pronoun will include the corresponding masculine, feminine and neuter forms, and (ii) words in the singular include the plural
and in the plural include the singular.

 

(c)        Severability. If any provision of this Agreement shall be invalid or unenforceable in any jurisdiction, such invalidity
or unenforceability shall not affect the validity or enforceability of the remainder of this Agreement in that jurisdiction or
the validity or enforceability of any provision of this Agreement in any other jurisdiction.

 

(d)        Entire Agreement; Amendments. This Agreement, together with the other Purchase Documents, supersedes all other prior oral
or written agreements among the parties, their affiliates and persons acting on their behalf with respect to the matters discussed
herein, and contain the entire understanding of the parties with respect to the matters covered herein and therein and, except
as specifically set forth herein or therein, none of the parties makes any representation, warranty, covenant or undertaking with
respect to such matters. No provision of this Agreement may be amended other than by an instrument in writing signed by the parties.
No provision hereof may be waived other than by an instrument in writing signed by the party against whom enforcement is sought.

 

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(e)         Notices.
Any notices, consents, waivers or other communications required or permitted to be given under the terms of this Agreement
must be in writing and will be deemed to have been delivered: (a) upon receipt, when delivered personally; (b) upon receipt,
when sent by facsimile (provided confirmation of transmission is mechanically or electronically generated and kept on file by
the sending party and either receipt of notice is affirmatively confirmed or the sender follows up with another method of
delivery provided hereunder within two (2) Business Days thereafter); or (c) one Business Day after deposit with an
overnight courier service, in each case properly addressed to the party to receive the same. The addresses and facsimile
numbers for such communications shall be as set forth on the signature page of such party hereto; provided, that any
notice to the Company shall also include a copy to Ellenoff Grossman & Schole LLP, 1345 Avenue of the Americas,
11th Floor, New York, NY 10105, Attn: Douglas S. Ellenoff, Esq. and Richard Baumann; Esq., Facsimile No.: (212)
370-7889. Written confirmation of receipt (A) given by the recipient of such notice, consent, waiver or other communication,
(B) mechanically or electronically generated by the sender’s facsimile machine containing the time, date, recipient
facsimile number and an image of the first page of such transmission or (C) provided by an overnight courier service shall be
rebuttable evidence of personal service, receipt by facsimile or receipt from an overnight courier service in accordance with
clause (a) or (c) above, respectively.

 

(f)         Successors and Assigns. This Agreement shall be binding upon and inure to the benefit of the parties and their respective
successors and assigns. None of the parties shall assign this Agreement or any of their respective rights or obligations hereunder
without the prior written consent of the other parties.

 

(g)        No Third Party Beneficiaries. This Agreement is intended for the benefit of the parties hereto and their respective permitted
successors and assigns, and is not for the benefit of, nor may any provision hereof be enforced by, any other person.

 

(h)        Survival. The representations, warranties and covenants of the parties hereto shall survive the Closing and the delivery
of the Purchased Securities.

 

(i)         Further Assurances. Each party shall use its reasonable best efforts to do and perform, or cause to be done and performed,
all such further acts and things, and shall execute and deliver all such other agreements, certificates, instruments and documents,
as any other party may reasonably request in order to carry out the intent and accomplish the purposes of this Agreement and the
consummation of the transactions contemplated hereby.

 

(j)         No Strict Construction. The language used in this Agreement will be deemed to be the language chosen by the parties to
express their mutual intent, and no rules of strict construction will be applied against any party.

 

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(k)        Indemnification.

 

(i)         In consideration of each Investor’s execution and delivery of the Purchase Documents to which it is a party and consummating
the Securities Purchase, in addition to the Company’s other obligations under the Purchase Documents, the Company and its
successors and assigns (collectively, the “Indemnifying Parties”) shall defend, protect, indemnify and
hold harmless each Investor and its successors and assigns and all of their respective stockholders, partners, members, officers,
directors, employees and direct or indirect investors and any of the foregoing Persons’ agents or other representatives
(including, without limitation, those retained in connection with the transactions contemplated by this Agreement) (collectively,
the “Indemnitees”) from and against any and all actions, causes of action, suits, claims, losses, costs,
penalties, fees, liabilities and damages, and expenses in connection therewith (irrespective of whether any such Indemnitee is
a party to the action for which indemnification hereunder is sought), and including reasonable attorneys’ fees and disbursements
(the “Indemnified Liabilities”), incurred by any Indemnitee as a result of, or arising out of, or relating
to (x) any misrepresentation or breach of any representation or warranty made by any Indemnifying Party to the Indemnitee in this
Agreement or the Warrants, (y) any breach of any covenant, agreement or obligation of any Indemnifying Party to the Indemnitee
contained in this Agreement or the Warrants or (z) any cause of action, suit, proceeding or claim brought or made against such
Indemnitee by a third party (including for these purposes a derivative action brought on behalf of any Indemnifying Party) or
which otherwise involves such Indemnitee that arises out of or results from (A) the execution, delivery, performance or enforcement
of this Agreement, (B) any transaction financed or to be financed in whole or in part, directly or indirectly, with the proceeds
of the issuance of the Purchased Securities, or (C) the status of such Investor or its successors or assigns either as an investor
in an Indemnifying Party pursuant to the transactions contemplated by this Agreement or as a party to this Agreement (including,
without limitation, as a party in interest or otherwise in any action or proceeding for injunctive or other equitable relief);
but excluding for purposes of this clause (z), any actions, suits, proceedings or claims arising solely out of or relating to
such Investor’s breach of this Agreement or any other Purchase Document to which such Investor is a party or otherwise bound.
To the extent that the foregoing undertaking by an Indemnifying Party may be unenforceable for any reason, such Indemnifying Party
shall make the maximum contribution to the payment and satisfaction of each of the Indemnified Liabilities which is permissible
under applicable law.

 

(ii)        Promptly after receipt by an Indemnitee under this Section 7(k) of notice of the commencement of any action or proceeding
(including any governmental action or proceeding) involving an Indemnified Liability, such Indemnitee shall, if a claim in respect
thereof is to be made against any Indemnifying Party under this Section 7(k), deliver to the applicable Indemnifying Party
a written notice of the commencement thereof, and such Indemnifying Party shall have the right to participate in, and, to the
extent such Indemnifying Party so desires, to assume control of the defense thereof with counsel mutually satisfactory to such
Indemnifying Party and the Indemnitee; provided, however, that an Indemnitee shall have the right to retain its
own counsel with the fees and expenses of such counsel to be paid by such Indemnifying Party if: (A) such Indemnifying Party has
agreed in writing to pay such fees and expenses; (B) such Indemnifying Party shall have failed to promptly assume the defense
of such Indemnified Liability and to employ counsel reasonably satisfactory to such Indemnitee in any such Indemnified Liability;
or (C) the named parties to any such Indemnified Liability (including any impleaded parties) include both such Indemnitee and
such Indemnifying Party, and such Indemnitee shall have been advised by outside counsel that a conflict of interest is likely
to exist if the same counsel were to represent such Indemnitee and such Indemnifying Party (in which case, if such Indemnitee
notifies such Indemnifying Party in writing that it elects to employ separate counsel at the expense of such Indemnifying Party,
then such Indemnifying Party shall not have the right to assume the defense thereof and such counsel shall be at the expense of
such Indemnifying Party), provided, further, that in the case of clause (C) above such Indemnifying Party shall not be responsible
for the reasonable fees and expenses of more than one (1) separate legal counsel for the Indemnitees. The Indemnitee shall reasonably
cooperate with each applicable Indemnifying Party in connection with any negotiation or defense of any such action or Indemnified
Liability by such Indemnifying Party and shall furnish to such Indemnifying Party all information reasonably available to the
Indemnitee which relates to such action or Indemnified Liability. Each of the Indemnifying Party and the Indemnitee shall keep
the other reasonably apprised at all times as to the status of the defense or any settlement negotiations with respect thereto.
An Indemnifying Party shall not be liable for any settlement of any action, claim or proceeding, or the Indemnitee’s consent
to any judgment, effected without its prior written consent, provided, however, that such Indemnifying Party shall
not unreasonably withhold, delay or condition its consent. No Indemnifying Party shall, without the prior written consent of the
Indemnitee, consent to entry of any judgment or enter into any settlement or other compromise which does not include as an unconditional
term thereof the giving by the claimant or plaintiff to such Indemnitee of a release from all liability in respect to such Indemnified
Liability or litigation, and such settlement shall not include any admission as to fault on the part of the Indemnitee. Following
indemnification as provided for hereunder, each applicable Indemnifying Party shall be subrogated to all rights of the Indemnitee
with respect to all third parties, firms or corporations relating to the matter for which indemnification has been made. The failure
to deliver written notice to the an Indemnifying Party within a reasonable time of the commencement of any such action shall not
relieve such Indemnifying Party of any liability to the Indemnitee under this Section 7(k), except to the extent that such
Indemnifying Party is materially and adversely prejudiced in its ability to defend such action.

 

    	9

    	 

    

 

(iii)       The indemnification required by this Section 7(k) shall be made by periodic payments of the amount thereof during the course
of the investigation or defense, within ten (10) days after bills are received or Indemnified Liabilities are incurred.

 

(iv)       The indemnity agreement contained herein shall be in addition to (A) any cause of action or similar right of the Indemnitee against
any Indemnifying Party or others, and (B) any liabilities such Indemnifying Party may be subject to pursuant to the law.

 

(l)          Waiver of Rights under Series A-2 Warrants and Series B-2 Warrants. Each Investor hereby waives, with respect to this Agreement
and the other Purchase Documents and the consummation by the Company of the transactions contemplated hereby and thereby, any
rights that such Investor may have under (and any failure of the Company to comply with the notice, timing and other requirements
of) (i) Section 16(m) of such Investor’s Insider Purchase Agreement, (ii) Sections 2(b), 2(f) and 17 of such Investor’s
Pubco Series A-2 Warrant and (iii) Section 2(b) and 2(f) of such Investor’s Pubco Series B-2 Warrant. The Company and each
Investor hereby agrees that any reference to “Investor Warrants” under each Investor’s Series A-2 Warrants and
Series B-2 Warrants will include the Series A-3 Warrants and Series B-3 Warrants. The Company further agrees that any reference
to “Investor Warrants” under any other Series A-2 Warrant, Series B-2 Warrant or any Series A-1 Warrant or Series
B-1 Warrant will include the Series A-3 Warrants and the Series B-3 Warrants.

 

(m)        Most Favored Nation. The Company hereby represents and warrants as of the date hereof and covenants and agrees from and
after the date hereof that none of the terms offered to any Person (other than the New Investors pursuant to the New Investor
Exchange Agreements or the Insider Investors under the Insider Purchase Agreements) with respect to any consent, release, amendment,
settlement or waiver, in each case, relating to the terms, conditions and transactions contemplated hereby (each a “Superior
Document”), is or will be more favorable to such Person than those of the Investors and this Agreement. If, and
whenever on or after the date hereof, the Company enters into a Superior Document, then (i) such applicable party shall provide
notice thereof to each Investor immediately following the occurrence thereof and (ii) the terms and conditions of this Agreement
shall be, without any further action by any Investor or any other party hereto, automatically amended and modified in an economically
and legally equivalent manner such that each Investor shall receive the benefit of the more favorable terms and/or conditions
(as the case may be) set forth in such Superior Document, provided that upon written notice to each other party hereto at any
time an Investor may elect not to accept the benefit of any such amended or modified term or condition, in which event the term
or condition contained in this Agreement shall apply to such Investor as it was in effect immediately prior to such amendment
or modification as if such amendment or modification never occurred with respect to such Investor. The provisions of this Section
7(l) shall apply similarly and equally to each Superior Document.

 

    	10

    	 

    

 

(n)        Independent Nature of Investor’s Obligations and Rights. The obligations of each Investor under this Agreement or
the other Purchase Documents are several and not joint with the obligations of any other Person, including, without limitation,
any of the Investors (each, an “Other Person”), and each Investor shall not be responsible in any way
for the performance of the obligations of any Other Person under any other Purchase Document or similar agreement of any Other
Person (the “Other Documents”). Nothing contained herein or in any Other Document or any other Purchase
Document, and no action taken by an Investor pursuant hereto, shall be deemed to constitute such Investor and any Other Person(s)
as a partnership, an association, a joint venture or any other kind of entity, or create a presumption that such Investor and
Other Person(s) are in any way acting in concert or as a group with respect to such obligations or the transactions contemplated
by this Agreement or any Other Documents or any other Purchase Document, and the Company acknowledges that no Investor is acting
in concert or as a group with any Other Person respect to such obligations or the transactions contemplated by this Agreement,
any Other Document and any other Purchase Document. The Company and each Investor confirm that each Investor has independently
participated in the negotiation of the transactions contemplated hereby with the advice of its own counsel and advisors. Each
Investor shall be entitled to independently protect and enforce its rights, including, without limitation, the rights arising
out of this Agreement, any Other Document or out of any other Purchase Documents, and it shall not be necessary for any Other
Person to be joined as an additional party in any proceeding for such purpose.

 

[Signature pages follow]

 

    	11

    	 

    

 

IN WITNESS WHEREOF,
the Company and the Investors have executed this Agreement as of the date set forth on the first page of this Agreement.

 

	 	THE COMPANY:
	 	 
	 	TEMPUS APPLIED SOLUTIONS HOLDINGS, INC.
	 	 	 
	 	By:	/s/ Benjamin Scott Terry
	 	 	Name:  Benjamin Scott Terry
	 	 	Title:    Chief Executive Officer
	 	 
	 	INVESTORS:
	 	 
	 	CHART ACQUISITION GROUP LLC
	 	 	 
	 	By:  	The Chart Group L.P.
	 	 	 
	 	 	By:	/s/ Christopher D. Brady
	 	 	 	Name:  Christopher D. Brady
	 	 	 	Title:    Manager
	 	 	 	 

 

[Signature Page to Securities Purchase Agreement]

 

    	 

    	 

    

 

	 	INVESTORS (Cont.):
	 	 
	 	/s/ Joseph Wright
	 	Joseph Wright
	 	 	 
	 	COWEN INVESTMENTS LLC
	 	 	 
	 	By:	/s/ Owen Littman
	 	 	Name:  Owen Littman
	 	 	Title:    Authorized Signatory
	 	 	 

 

[Signature Page
to Securities Purchase Agreement]

 

    	 

    	 

    

 

SCHEDULE 4(c)(ii)

 

Filing of Form Ds with the SEC in connection
with the private offer and sale of the Purchased Securities by the Company to the Investors pursuant to Rule 506(b) under the
1933 Act.

 

    	 

    	 

    

 

Exhibit A

Investors

 

	Investor	 	Aggregate Purchase Price	 	 	No. of Common Shares	 	 	No. of Series A-3 Warrants	 	 	No. of Series B-3 Warrants	 
	Chart Acquisition Group LLC	 	$	616,672.00	 	 	 	154,168	 	 	 	115,626	 	 	 	38,542	 
	Joseph Wright	 	$	33,328.00	 	 	 	8,332	 	 	 	6,249	 	 	 	2,083	 
	Cowen Investments LLC	 	$	350,000.00	 	 	 	87,500	 	 	 	65,625	 	 	 	21,875	 
	TOTAL	 	$	1,000,000.00	 	 	 	250,000	 	 	 	187,500	 	 	 	62,500	 

 

    	 

    	 

    

 

Exhibit B

Form of Series A-3 Warrant

 

See attached.

 

    	 

    	 

    

 

Exhibit C

Form of Series B-3 Warrant

 

See attached

 

    	 

    	 

    

 

Exhibit D

Form of Founders RRA Amendment

 

See attachedExhibit 10.2

 

EXECUTION COPY 

 

THIRD AMENDMENT TO REGISTRATION RIGHTS
AGREEMENT 

 

THIS THIRD AMENDMENT
TO REGISTRATION RIGHTS AGREEMENT (this “Third Amendment”) is made and entered into as of August 14,
2015 by and among: (i) Chart Acquisition Corp., a Delaware corporation (the “Company”); (ii) Tempus Applied
Solutions Holdings, Inc., a Delaware corporation (“Pubco”); (iii) Chart Acquisition Group LLC, a Delaware
limited liability company (“Sponsor”); (iv) Cowen Investments LLC (“Cowen”);
and (v) certain of the other persons or entities described as Holders in the Registration Rights Agreement (as defined below) and
named on the signature pages hereto who have executed this Third Amendment. Capitalized terms used but not otherwise defined herein
shall have the respective meanings assigned to such terms in the Registration Rights Agreement.

 

RECITALS

 

WHEREAS, the Company,
Pubco, Sponsor, Cowen and the other Holders named therein are parties to that certain Registration Rights Agreement, dated as of
December 13, 2012 (as amended, including, without limitation, as amended by the First Amendment to Registration Rights Agreement,
dated as of June 20, 2015, the Second Amendment to Registration Rights Agreement, dated as of July 31, 2015, and as amended by
this Third Amendment, the “Registration Rights Agreement”), pursuant to which Pubco granted certain registration
rights to the Holders with respect to Pubco’s securities;

 

WHEREAS, Pubco is
entering into that certain Securities Purchase Agreement, dated as of the date hereof (the “Securities Purchase Agreement”),
with Sponsor, Mr. Joseph Wright and Cowen (collectively, the “Investors”), pursuant to which on the date
hereof Pubco will issue to each Investor shares of Pubco Common Stock (the “Purchased Common Shares”),
Series A-3 Warrants to purchase Pubco Common Stock or Pubco Series A Preferred Stock (the “Series A-3 Warrants”)
and Series B-3 Warrants to purchase Pubco Common Stock or Pubco Series A Preferred Stock (the “Series B-3 Warrants”
and, together with the Series A-3 Warrants, the “Purchased Warrants” and, collectively with the Purchased
Common Shares, the “Purchased Securities”);

 

WHEREAS, the parties
hereto desire to amend the Registration Rights Agreement to reflect the transactions contemplated by the Securities Purchase Agreement,
including, without limitation, the issuance of the Purchased Securities thereunder; and

 

WHEREAS, pursuant
to Section 5.5 of the Registration Rights Agreement, the Registration Rights Agreement can be amended with the written consent
of the Company and the Holders of at least 66-2/3% of the Registrable Securities at the time in question (provided, that any amendment
that adversely affects one Holder, solely in its capacity as a holder of the shares of capital stock of the Company, in a manner
that is materially different from the other Holders (in such capacity) shall require the consent of the Holder so affected).

 

NOW, THEREFORE,
in consideration of the premises and the mutual promises herein made, and in consideration of the representations, warranties
and covenants herein contained, and intending to be legally bound hereby, the parties hereto agree as follows:

 

1.            Amendments
to Registration Rights Agreement. The Parties hereby agree to the following amendments to the Registration Rights Agreement:

 

(a)           The defined
terms in this Third Amendment, including in the preamble and recitals hereto, are hereby added to the Registration Rights Agreement
as if they were set forth therein.

 

    	 

    	 

    

 

(b)           Section 1.1
of the Registration Rights Agreement is hereby amended to delete the definition of the term “Financing Securities”
and replace it with the following:

 

“Financing
Securities” shall mean (i) the shares of Pubco Common Stock and Pubco Investor Warrants issued in the Parent Merger
to the holders of Parent Financing Sub Series B Non-Voting Preferred Stock, par value $0.0001 per share, (ii) the Purchased Common
Shares and Purchased Warrants issued under the Securities Purchase Agreement, (iii) the shares of Pubco Common Stock or Pubco Series
A Preferred Stock issuable upon the exercise and/or redemption of such Pubco Investor Warrants or Purchased Warrants, (iv) the
shares of Pubco Common Stock issuable upon the conversion of such Pubco Series A Preferred Stock and (v) any other securities of
the Pubco or any successor entity issued in consideration of (including as a stock split, dividend or distribution) or in exchange
for any of the securities described in clauses (i) through (iv) above.

 

(c)           The parties
hereby agree that the term “Registrable Security” shall include any Purchased Securities issued by Pubco
under the Securities Purchase Agreement, and any other securities of Pubco or any successor entity issued in consideration of (including
as a stock split, dividend or distribution) or in exchange for any of such securities.

 

2.            Miscellaneous.
Except as expressly provided in this Third Amendment, all of the terms and provisions in the Registration Rights Agreement are
and shall remain in full force and effect, on the terms and subject to the conditions set forth therein. This Third Amendment does
not constitute, directly or by implication, an amendment or waiver of any provision of the Registration Rights Agreement, or any
other right, remedy, power or privilege of any party thereto, except as expressly set forth herein. Any reference to the Registration
Rights Agreement in the Registration Rights Agreement or any other agreement, document, instrument or certificate entered into
or issued in connection therewith shall hereinafter mean the Registration Rights Agreement, as amended by this Third Amendment
(or as the Registration Rights Agreement may be further amended or modified after the date hereof in accordance with the terms
thereof). The terms of this Third Amendment shall be governed by and construed in a manner consistent with the provisions of the
Registration Rights Agreement, including Section 5.4 thereof.

 

[REMAINDER OF PAGE
INTENTIONALLY LEFT BLANK; SIGNATURE PAGES FOLLOW]

 

    	2

    	 

    

 

IN WITNESS WHEREOF,
each party hereto has signed or has caused to be signed by its officer thereunto duly authorized this Third Amendment to Registration
Rights Agreement as of the date first above written.

 

	 	Company:
	 	 
	 	CHART ACQUISITION CORP.
	 	 
	 	By:	 
	 	 	Name:  Christopher D. Brady
	 	 	Title:  President
	 	 
	 	Pubco:
	 	 
	 	TEMPUS APPLIED SOLUTIONS HOLDINGS, INC.
	 	 
	 	By:	 
	 	 	Name:  Benjamin Scott Terry
	 	 	Title:  Chief Executive Officer
	 	 
	 	Holders:
	 	 
	 	CHART ACQUISITION GROUP LLC
	 	 
	 	By: The Chart Group L.P.
	 	 	 
	 	By:	 
	 	 	Name:  Christopher D. Brady
	 	 	Title:  Manager
	 	 
	 	COWEN INVESTMENTS LLC
	 	 
	 	By:	 
	 	 	Name:  
	 	 	Title:
	 	 
	 	THE CHART GROUP L.P.
	 	 
	 	By:	 
	 	 	Name:  Christopher D. Brady
	 	 	Title:  Manager

 

[Signature Page to Third Amendment to
Registration Rights Agreement]

 

    	3

    	 

    

 

Holders (cont.):

 

	 	 	 
	Abdulwahab Al-Nakib	 	Geoffry Nattans
	 	 	 
	 	 	 
	
        Joseph Boyle
	 	Governor Thomas Ridge
	 	 	 
	 	 	 
	Christopher Brady	 	Charlene Ryan
	 	 	 
	 	 	 
	David Collier	 	Margaret Saracco
	 	 	 
	 	 	 
	Senator Joseph Robert Kerrey 	 	Timothy N. Teen
	 	 	 
	 	 	 
	Deirdre Kilmartin	 	Cole Van Nice
	 	 	 
	 	 	 
	Michael LaBarbera	 	H. Whitney Wagner
	 	 	 
	 	 	 
	Khaled El-Marsafy (Fourth and Market)	 	Joseph R. Wright
	 	 	 
	 	 	 
	Matthew McCooe	 	Young-Gak Yun
	 	 	 
	 	 	 
	Manuel D. Medina	 	 

 

 

[Signature Page to Third Amendment to
Registration Rights Agreement]

 

4

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