Exhibit
10.44


 


SECOND
AMENDMENT TO SECURITIES PURCHASE AGREEMENT


 


This
SECOND AMENDMENT TO SECURITIES PURCHASE AGREEMENT, dated as of July 30 2021 (this “Amendment”), is made and entered
into by and among FreightHub, Inc., a Delaware corporation (the “Company”), and the undersigned parties (the “Holders”),
in connection with that certain Securities Purchase Agreement, dated as of February 9, 2021, as amended by that certain Amendment to
Securities Purchase Agreement dated as of May 24, 2021 (the “Agreement”), by and among the Company and each purchaser
identified on the signature pages thereto (each, including its successors and assigns, a “Purchaser” and collectively,
the “Purchasers”). As used in this Amendment, capitalized terms which are not defined herein shall have the meanings
ascribed to such terms in the Agreement.


 


W
I T N E S S E T H


 


WHEREAS,
pursuant to Section 5.5 of the Agreement, any amendment to the Agreement requires a written instrument signed by Purchasers which purchased
at least 50.1% in interest of the Securities based on the initial Subscription Amounts under the Agreement;


 


WHEREAS,
the Company requires additional funds for working capital prior to the Closing and has reached an agreement with certain Purchasers to
fund additional May Convertible Notes pursuant to the May Note Purchase Agreement up to, in the aggregate, $1,000,000 which will be convertible
into Preferred Stock on the Closing Date and which may depending upon whether certain elections are made by certain Purchasers under
the Agreement, reduce cash Subscription Amounts otherwise to be received by the Company at the Closing;


 


WHEREAS,
the Holders purchased at least 50.1% in interest of the Securities based on the initial Subscription Amounts under the Agreement; and


 


WHEREAS,
the Company and the Holders desire to amend certain provisions of the Agreement as further set forth herein in connection with the issuance
by the Company of the convertible notes referred to above and to reflect certain additional agreements of the parties.


 


NOW,
THEREFORE, for good and valuable consideration the receipt and adequacy of which are hereby acknowledged, the Company and the Holders
hereby agree as follows:


 


1.
Amendment and Restatement of Existing Definitions in Section 1.1 of the Agreement. The following terms in Section 1.1 of the Agreement
shall be amended and restated as follows:


 


“May
Convertible Notes” means Fr8Hub’s Convertible Promissory Notes, issued pursuant to the May Note Purchase Agreement, held
by certain Purchasers with an aggregate principal amount of $2,608,842. Schedule C to this Agreement sets forth a list of (i)
the name of each Purchaser that is purchasing shares of Preferred Stock and Warrants under this Agreement through the cancellation of
May Convertible Notes pursuant to the terms thereof and as specified in this Agreement, (ii) a description of the Convertible Note(s)
held by each such Purchaser, and (iii) the aggregate amount of outstanding principal amount and accrued and unpaid interest of each May
Convertible Note that is being converted by such Purchaser (as the rate of 266.67% thereof) into shares of Preferred Stock and Warrants
pursuant to the terms of such May Convertible Notes and as specified in this Agreement.


 


[Second
Amendment to Securities Purchase Agreement]


 




    	 



     


    

 


“May
Note Purchase Agreement” means that certain Note Purchase Agreement, dated as of May 24, 2021, among Fr8Hub and the purchasers
of May Convertible Notes named therein, as amended by that certain Amendment No. 1 to Note Purchase Agreement dated as of July 30, 2021.


 


“Post-Merger
Company Preferred Stock” means the up to 55,914,267 shares of the Post-Merger Company’s Series Convertible Preferred
Stock issued hereunder in exchange for the Preferred Stock having the rights, preferences and privileges set forth in the Post-Merger
Company Certificate of Designation, in the form of Exhibit C hereto.


 


“Preferred
Stock” means the up to 12,616,726 shares of the Company’s Series A3 Convertible Preferred Stock issued hereunder having
the rights, preferences and privileges set forth in the Fourth Amended and Restated Certificate of Incorporation.


 


“Stated
Value” means the stated value per share of Preferred Stock which shall equal the product of (A) the quotient determined by
dividing (I) the difference between (a) 27,800,598 and (b) the quotient determined by dividing (i) the aggregate cash Subscription
Amounts (excluding for such purposes Subscription Amounts derived from Convertible Notes), divided by (ii) 1.5, divided by (II) 17,738,968,
and (B) 3.


 


2.
Amendments to Section 2.1. The first sentence of Section 2.1 shall be amended and restated as follows: “On the Closing Date,
upon the terms and subject to the conditions set forth herein, the Company agrees to sell, and the Purchasers, severally and not jointly,
agree to purchase, up to an aggregate of up to $47,926,514 in Stated Value of shares of Preferred Stock pursuant to the terms of this
Agreement.


 


3.
Amendments to Section 4.18. Section 4.18(a)(iv) is hereby amended and restated as follows: “as to Securities issued for
conversion of May Convertible Notes, a Series D Warrant registered in the name of such Purchaser to purchase up to a number of shares
of common stock of the Post-Merger Company equal to 100% of the Post Merger Company Conversion Shares initially issuable upon conversion
of such Purchaser’s Post-Merger Preferred (assuming for such purposes that the allocation of the Issuable Maximum as to such Post-Merger
Company Conversion Shares is 2,323,921.)


 


4.
Acknowledgement of Revised Certificate of Designation. The parties hereto acknowledge and agree to the revised Certificate of
Designation, Exhibit C to the Agreement, as attached hereto.


 


[Second
Amendment to Securities Purchase Agreement]


 




    	 



     


    

 


5.
Amendments to ATW Signature Pages. The parties hereto acknowledge and agree to the revised executed signature pages to the Agreement
of ATW Opportunities Master Fund, L.P. and ATW Master Fund II attached to this Amendment as Annex A and Annex B.


 


6.
Amendments to Schedule A, Schedule B and Schedule C. The parties hereto acknowledge and agree that the revised Schedule A,
Schedule B and Schedule C to the Agreement as attached hereto, which in each case have been revised to reflect thereon
the accrued and unpaid interest under October Convertible Notes, January Convertible Notes or May Convertible Notes, as applicable, into
shares of Preferred Stock and Warrants at Closing, as contemplated by the definitions of October Convertible Notes, January Convertible
Notes, May Convertible Notes and Subscription Amount set forth in the Agreement.


 


7.
Miscellaneous.


 


(a)
Successors and Assigns. This Amendment shall be binding upon and inure to the benefit of and be enforceable by the respective
successors and permitted assigns of the parties hereto.


 


(b)
No Modification. Except as expressly set forth herein, the Agreement is and shall remain unchanged and in full force and effect,
and nothing contained in this Amendment shall, by implication or otherwise, limit, impair, constitute a waiver of, or otherwise affect
the rights and remedies of the parties, or shall alter, modify, amend or in any way affect any of the terms, conditions, obligations,
covenants or agreements contained in the Agreement.


 


(c)
Governing Law. This Amendment and all actions arising out of or in connection with this Amendment shall be governed by and construed
in accordance with the internal laws of the State of New York, without regard to the principles of conflicts of law thereof.


 


(d)
Counterparts. This Amendment may be executed in any number of counterparts, including counterparts transmitted by facsimile or
other electronic transmission, and by different parties hereto in separate counterparts, with the same effect as if all parties had signed
the same document. All such counterparts shall be deemed an original, shall be construed together and shall constitute one and the same
instrument.


 


[Signature
Pages Follow]


 


[Second
Amendment to Securities Purchase Agreement]


 




    	 



     


    

 


The
parties hereto have caused this Second Amendment to be duly executed and delivered by their duly authorized officers as of the day and
year first above written.


 


	 	FREIGHTHUB,
    INC.
	 	 	                
	 	By:	 /s/
    Paul Freudenthaler  
	 	Name:	 Paul
    Freudenthaler  
	 	Title:	 Chief
    Financial Officer 


 




    	 



     


    




 


The
parties hereto have caused this Second Amendment to be duly executed and delivered by their duly authorized officers as of the day and
year first above written.


 


Name
of Purchaser: __________________________________________________________________





Signature
of Authorized Signatory of Purchaser: ___________________________________________





Name
of Authorized Signatory: _________________________________________________________





Title
of Authorized Signatory: __________________________________________________________


 




    	 



     


    

 


Revised
Certificate of Designation


 


(Attached
hereto)


 




    	 



     


    

 





Revised
Schedule A, Schedule B and Schedule C


 


(Attached
hereto)


 




    	 



     


    

 





SCHEDULE
A


 


October
Convertible Notes


 


	Name
    of Purchaser	 	Description
                                            of

    October
    Convertible Notes Converted
	 	Principal
                                            Amount

                                                                     and
                                            Accrued and

    Unpaid
    Interest Converted*

	ATW
    Master Fund II, L.P.	 	Note
    No. 0002 for $304,421 issued on October 7, 2020 	 	Principal:
                                            $304,421

     

    Interest:
    $11,342.80

     

	ATW
    Opportunities Master Fund, L.P.	 	Note
    No. 0001 for $1,500,000 issued on October 7, 2020; Note No. 0018 for $550,425 issued on November 2, 2020	 	Principal:
                                            $2,050,425

     

    Interest:
    $72,753.70

     

	Winston
    J. Churchill	 	Note
    No. 0011 for $67,021 issued on October 9, 2020	 	Principal:
                                            $67,021

     

    Interest:
    $2,423.77

     

	Jason
    Epstein	 	Note
    No. 0008 for $123,669 issued on October 16, 2020	 	Principal:
                                            $123,669

     

    Interest:
    $4,354.88

     

	Grays
    West Ventures LLC	 	Note
    No. 0007 for $136,199 issued on October 8, 2020	 	Principal:
                                            $136,199

     

    Interest:
    $4,944.21

     

	Kerry
    Propper	 	Note
    No. 0010 for $71,473 issued on October 19, 2020	 	Principal:
                                            $71,473

     

    Interest:
    $2,486.88

     

	Kli
    Capital LLP (f/k/a BNSG Capital LLP)	 	Note
    No. 0005 for $234,871 issued on October 16, 2020	 	Principal:
                                            $234,871

     

    Interest:
    $8,268.75

     

	M&M
    Energy Investors LLC	 	Note
    No. 0012 for $24,384 issued on October 8, 2020	 	Principal:
                                            $24,384

     

    Interest:
    $885.17

     

	Ramiro
    E. Menchaca Sr.	 	Note
    No. 0015 for $9,067 issued on October 9, 2020	 	Principal:
                                            $9,067

     

    Interest:
    $327.90

     

	Ignacio
    Mounetou	 	Note
    No. 0006 for $221,632 issued on October 14, 2020	 	Principal:
                                            $221,632

     

    Interest:
    $7,863.38

     

	Ramiro
    E. Menchaca II	 	Note
    No. 0009 for $81,072 issued on October 22, 2020	 	Principal:
                                            $81,072

     

    Interest:
    $2,787.54

     

	Sharbaugh
    Trust	 	Note
    No. 0014 for $10,013 issued on October 9, 2020	 	Principal:
                                            $10,013

     

    Interest:
    $362.11

     

	Yaron
    Eitan	 	Note
    No. 0016 for $1,399 issued on October 16, 2020	 	Principal:
                                            $1,399

     

    Interest:
    $49.25

     

	Yuri
    Kokush	 	Note
    No. 0004 for $250,000 issued on October 13, 2020	 	Principal:
                                            $250,000

     

    Interest:
    $8,904.11

     

	JADI
    Trust	 	Note
    No. 0003 for $400,000 issued on October 16, 2020	 	Principal:
                                            $400,000

     

    Interest:
    $14,082.19

     

	Michael
    Richter	 	Note
    No. 0013 for $18,293 issued on October 8, 2020	 	Principal:
                                            $18,293

     

    Interest:
    $664.06

     

	Emanuel
    Zareh	 	Note
    No. 0017 for $481 issued on October 14, 2020	 	Principal:
    $481 Interest: $17.07





 


*Interest
calculated through June 30, 2021.


 




    	 



     


    

 


SCHEDULE
B


 


January
Convertible Notes


 


	Name
    of Purchaser	 	Description
                                            of

    

    January
    Convertible Notes

    Converted
	 	Principal
                                            Amount

                                                                     and
                                            Accrued and

    

    Unpaid
    Interest Converted*

	ATW
    Opportunities Master Fund, L.P.	 	Note
    No. 0001 for $1,000,000 issued January, 2021	 	Principal:
                                            $1,000,000

     

    Interest:
    $19,726.03






 


*Interest
calculated through June 30, 2021.


 




    	 



     


    

 





SCHEDULE
C


 


May
Convertible Notes


 


	
    Name
    of Purchaser
	 	

    

    

    

    Description
    of

    

    May
    Convertible Notes 

    

    Converted
	 	Principal
                                            Amount

                                                                     and
                                            Accrued and

    

    Unpaid
    Interest Converted*

	ATW
    Opportunities Master Fund, L.P.	 	Note
    No. 0001 for $1,000,000 issued May 24, 2021	 	Principal:
                                            $1,000,000

     

    Interest:
    $5,068.49

     

	ATW
    Master Fund II, L.P.	 	Note
    No. 0002 for $608,842 issued June 23, 2021	 	Principal:
                                            $608,842

     

    Interest:
    $500.42

     

	ATW
    Opportunities Master Fund, L.P.	 	Note
    No. 3 for $1,000,000 issued July 30, 2021	 	Principal:
                                            $1,000,000

     

    Interest:
    $0



 


*Interest
calculated through June 30, 2021.


 




    	 



     


    

 


Annex
A


 


Amended
Signature Page of ATW Opportunities Master Fund, L.P.


 


(Attached
hereto)


 




    	 



     


    

 





PURCHASER
SIGNATURE PAGES TO fr8hub and husn SECURITIES PURCHASE AGREEMENT


 


IN
WITNESS WHEREOF, the undersigned have caused this Securities Purchase Agreement to be duly executed by their respective authorized signatories
as of the date first indicated above.


 


Name
of Purchaser: ATW Opportunities Master Fund, L.P., by ATW Partners Opportunities Fund GP, LLC, its General Partner


 


Signature of Authorized Signatory of Purchaser:
__/s/ Antonio Ruiz-Gimenez, Jr. _______________________ 


 


Name
of Authorized Signatory: Antonio Ruiz-Gimenez


 


Title
of Authorized Signatory: Managing Partner


 


Email
Address of Authorized Signatory: aruizg@atwpartners.com


 


Address
for Notice to Purchaser: 507 West 28th Street 1205, New York, NY 10001


 


Address
for Delivery of Securities to Purchaser (if not same as address for notice):


 


Subscription
Amounts:


 


Cash:
$4,100,850, subject to the final paragraph of this signature page. 

Principal of January Convertible Notes: $1,000,000


Principal
of October Convertible Notes: $2,050,425


Principal
of May Convertible Notes: $2,000,000


 


Shares
of Preferred Stock:


 


From
Cash (200%): 2,733,900, subject to the final paragraph of this signature page.


From
January Convertible Notes (250%): 833,333


From
October Convertible Notes (400%): 2,733,900


From
May Convertible Notes (266.67%): 2,318,971


 


Warrant
Shares (calculated per Section 4.18(a)): 2,733,900 Series A Warrant Shares (subject to the final paragraph of this signature page),
833,333 Series B Warrant Shares, 2,733,900 Series C Warrant Shares, and 2,318,971 Series D Warrant Shares.


 


EIN
Number: 85-1393078


 


ATW
Opportunities Master Fund, L.P. may in its sole discretion elect at any time prior to the Closing, by written notice of such election
delivered to the Company, to reduce its $4,100,850 cash subscription amount set forth above by all or any portion it may so elect of
the principal and accrued and unpaid interest of January Convertible Notes and/or May Convertible Notes being converted at Closing by
ATW Opportunities Master Fund, L.P. In the case of any such election by ATW Opportunities Master Fund, L.P. (i) the $4,100,850 cash subscription
amount set forth above shall automatically be reduced on a dollar-for-dollar basis to the extent of such election, (ii) the number of
shares of Preferred Stock issuable from cash at the rate of 200% set forth above shall be correspondingly reduced, and (iii) the number
of Series A Warrant Shares calculated per Section 4.18(a) set forth above shall be correspondingly reduced.


 


[SIGNATURE
PAGES CONTINUE]


 




    	 



     


    

 


Annex
B


 


Amended
Signature Page of ATW Master Fund II, L.P.


 




    	 



     


    

 





PURCHASER
SIGNATURE PAGES TO fr8hub and husn SECURITIES PURCHASE AGREEMENT


 


IN
WITNESS WHEREOF, the undersigned have caused this Securities Purchase Agreement to be duly executed by their respective authorized signatories
as of the date first indicated above.


 


Name
of Purchaser: ATW Master Fund II, L.P., by ATW Partners GP II, LLC, its General Partner


 


Signature of Authorized Signatory of Purchaser:
___/s/ Antonio Ruiz-Gimenez, Jr. ________ 


 


Name
of Authorized Signatory: Antonio Ruiz-Gimenez


 


Title
of Authorized Signatory: Managing Partner


 


Email
Address of Authorized Signatory: aruizg@atwpartners.com


 


Address
for Notice to Purchaser: 507 West 28th Street 1205, New York, NY 10001


 


Address
for Delivery of Securities to Purchaser (if not same as address for notice):


 


Subscription
Amounts:


 


Cash:
$608,842, subject to the final paragraph of this signature page. 

Principal of January Convertible Notes: None.


Principal
of October Convertible Notes $304,421.


Principal
of May Convertible Notes: $608,842


 


Shares
of Preferred Stock:


 


From
Cash (200%): 405,894, subject to the final paragraph of this signature page.


From
January Convertible Notes (250%): None.


From
October Convertible Notes (400%): 405,894


From
May Convertible Notes (266.67%): 541,193


 


Warrant
Shares (calculated per Section 4.18(a)): 405,894 Series A Warrant Shares (subject to the final paragraph of this signature page, 405,894
Series C Warrant Shares, and 541,193 Series D Warrant Shares.


 


EIN
Number: 82-1673294


 


ATW
Master Fund II, L.P. may in its sole discretion elect at any time prior to the Closing, by written notice of such election delivered
to the Company, to reduce its $608,842 cash subscription amount set forth above by all or any portion it may so elect of the principal
and accrued and unpaid interest of January Convertible Notes and/or May Convertible Notes being converted at Closing by ATW Master Fund
II, L.P. In the case of any such election by ATW Master Fund II, L.P. (i) the $608,842 cash subscription amount set forth above shall
automatically be reduced on a dollar-for-dollar basis to the extent of such election, (ii) the number of shares of Preferred Stock issuable
from cash at the rate of 200% set forth above shall be correspondingly reduced, and (iii) the number of Series A Warrant Shares calculated
per Section 4.18(a) set forth above shall be correspondingly reduced.