<PAGE>

            THIS WARRANT AND THE SHARES OF COMMON STOCK ISSUED UPON ITS
                    EXERCISE ARE SUBJECT TO THE RESTRICTIONS ON
                  TRANSFER SET FORTH IN SECTION 4 OF THIS WARRANT


Warrant No. ____                                       Number of Shares: 100,000
(subject to adjustment)                    Date of Issuance:  April 26, 2000


                                    I-MANY INC.

                           COMMON STOCK PURCHASE WARRANT

       I-many, Inc., a Delaware corporation (the "Company"), for value received,
hereby certifies that Silicon Valley Bank, or its registered assigns (the
"Registered Holder"), is entitled, subject to the terms and conditions set forth
below, to purchase from the Company, at any time or from time to time on or
after the earlier of (w) the closing date of a Qualified Public Offering (as
defined below), and (x) August 1, 2000 (the earlier of such dates being referred
to as the "First Exercise Date") and on or before 5:00 p.m. (Boston time) on the
second anniversary of the First Exercise Date, 100,000 shares of Common Stock,
$.0001 par value per share, of the Company, at a purchase price equal to (u)
$9.00 (in the event that this warrant became exercisable on the date set forth
in clause (w) above), or (v) the fair market value per share of Common Stock of
the Company on the First Exercise Date as determined by the Board of Directors
in its reasonable discretion, acting in good faith (in the event that this
warrant became exercisable on the date set forth in clause (x) above).  The
shares purchasable upon exercise of this Warrant, and the purchase price per
share, each as adjusted from time to time pursuant to the provisions of this
Warrant, are hereinafter referred to as the "Warrant Shares" and the "Purchase
Price," respectively.  For purposes hereof, "Qualified Public Offering" means
the first underwritten public offering for the account of the Company of its
common stock pursuant to a registration statement filed under the Securities Act
of 1933.  Following the determination by the Board of Directors of the fair
market value per share pursuant to clause (v) above, the Company shall promptly
so notify  the Registered Holder in writing.

       1.     EXERCISE.

              (a)    This Warrant may be exercised by the Registered Holder, in
whole or in part, by surrendering this Warrant, with the purchase form appended
hereto as EXHIBIT I duly executed by the Registered Holder or by the Registered
Holder's duly authorized attorney, at the principal office of the Company, or at
such other office or agency as the Company may designate, accompanied by payment
in full, in lawful money of the United States, of the Purchase Price payable in
respect of the number of Warrant Shares purchased upon such exercise.

              (b)    The Registered Holder may, at its option, elect to pay some
or all of the Purchase Price payable upon an exercise of this Warrant by
cancelling a portion of this Warrant exercisable for such number of Warrant
Shares as is determined by dividing (i) the total Purchase Price payable in
respect of the number of Warrant Shares being purchased upon such exercise by
(ii) the excess of the Fair Market Value per share of Common Stock (as defined
below) as of the

<PAGE>

Exercise Date (as defined in subsection 1(c) below) over the Purchase Price per
share.  If the Registered Holder wishes to exercise this Warrant pursuant to
this method of payment with respect to the maximum number of Warrant Shares
purchasable pursuant to this method, then the number of Warrant Shares so
purchasable shall be equal to the total number of Warrant Shares, minus the
product obtained by multiplying (x) the total number of Warrant Shares by (y) a
fraction, the numerator of which shall be the Purchase Price per share and the
denominator of which shall be the Fair Market Value per share of Common Stock as
of the Exercise Date.  The Fair Market Value per share of Common Stock shall be
determined as follows:

              (i)    If the Common Stock is listed on a national securities
exchange, the Nasdaq National Market or another nationally recognized trading
system as of the Exercise Date, the Fair Market Value per share of Common Stock
shall be deemed to be the average of the high and low reported sale prices per
share of Common Stock thereon on the trading day immediately preceding the
Exercise Date (provided that if no such price is reported on such day, the Fair
Market Value per share of Common Stock shall be determined pursuant to clause
(ii)).

              (ii)   If the Common Stock is not listed on a national securities
exchange, the Nasdaq National Market or another nationally recognized trading
system as of the Exercise Date, the Fair Market Value per share of Common Stock
shall be deemed to be the amount most recently determined by the Board of
Directors in good faith to represent the fair market value per share of the
Common Stock (including without limitation a determination for purposes of
granting Common Stock options or issuing Common Stock under an employee benefit
plan of the Company); and, upon request of the Registered Holder, the Board of
Directors (or a representative thereof) shall promptly notify the Registered
Holder of the Fair Market Value per share of Common Stock.  Notwithstanding the
foregoing, if the Board of Directors has not made such a determination within
the three-month period prior to the Exercise Date, then (A) the Board of
Directors shall make a determination of the Fair Market Value per share of the
Common Stock within 15 days of a request by the Registered Holder that it do so,
and (B) the exercise of this Warrant pursuant to this subsection 1(b) shall be
delayed until such determination is made.

              (c)    Each exercise of this Warrant shall be deemed to have been
effected immediately prior to the close of business on the day on which this
Warrant shall have been surrendered to the Company as provided in subsection
1(a) above (the "Exercise Date").  At such time, the person or persons in whose
name or names any certificates for Warrant Shares shall be issuable upon such
exercise as provided in subsection 1(d) below shall be deemed to have become the
holder or holders of record of the Warrant Shares represented by such
certificates.

              (d)    As soon as practicable after the exercise of this Warrant
in full or in part, and in any event within 10 days thereafter, the Company, at
its expense, will cause to be issued in the name of, and delivered to, the
Registered Holder, or as such Holder (upon payment by such Holder of any
applicable transfer taxes) may direct:

              (i)    a certificate or certificates for the number of full
Warrant Shares to which the Registered Holder shall be entitled upon such
exercise plus, in lieu of any fractional share to which the Registered Holder
would otherwise be entitled, cash in an amount determined pursuant to Section 3
hereof; and


                                        - 2 -
<PAGE>

              (ii)   in case such exercise is in part only, a new warrant or
warrants (dated the date hereof) of like tenor, calling in the aggregate on the
face or faces thereof for the number of Warrant Shares equal (without giving
effect to any adjustment therein) to the number of such shares called for on the
face of this Warrant minus the sum of (a) the number of such shares purchased by
the Registered Holder upon such exercise plus (b) the number of Warrant Shares
(if any) covered by the portion of this Warrant cancelled in payment of the
Purchase Price payable upon such exercise pursuant to subsection 1(b) above.

       2.     ADJUSTMENTS.

              (a)    ADJUSTMENT FOR STOCK SPLITS AND COMBINATIONS.  If the
Company shall at any time or from time to time after the date on which this
Warrant was first issued (the "Original Issue Date") effect a subdivision of the
outstanding Common Stock, the Purchase Price then in effect immediately before
that subdivision shall be proportionately decreased.  If the Company shall at
any time or from time to time after the Original Issue Date combine the
outstanding shares of Common Stock, the Purchase Price then in effect
immediately before the combination shall be proportionately increased.  Any
adjustment under this paragraph shall become effective at the close of business
on the date the subdivision or combination becomes effective.

              (b)    ADJUSTMENT FOR CERTAIN DIVIDENDS AND DISTRIBUTIONS.  In the
event the Company at any time, or from time to time after the Original Issue
Date shall make or issue, or fix a record date for the determination of holders
of Common Stock entitled to receive, a dividend or other distribution payable in
additional shares of Common Stock, then and in each such event the Purchase
Price then in effect immediately before such event shall be decreased as of the
time of such issuance or, in the event such a record date shall have been fixed,
as of the close of business on such record date, by multiplying the Purchase
Price then in effect by a fraction:

                     (1)    the numerator of which shall be the total number of
              shares of Common Stock issued and outstanding immediately prior to
              the time of such issuance or the close of business on such record
              date, and

                     (2)    the denominator of which shall be the total number
              of shares of Common Stock issued and outstanding immediately prior
              to the time of such issuance or the close of business on such
              record date plus the number of shares of Common Stock issuable in
              payment of such dividend or distribution;

provided, however, if such record date shall have been fixed and such dividend
is not fully paid or if such distribution is not fully made on the date fixed
therefor, the Purchase Price shall be recomputed accordingly as of the close of
business on such record date and thereafter the Purchase Price shall be adjusted
pursuant to this paragraph as of the time of actual payment of such dividends or
distributions.

              (c)    ADJUSTMENT IN NUMBER OF WARRANT SHARES.  When any
adjustment is required to be made in the Purchase Price pursuant to
subsections 2(a) or 2(b), the number of Warrant Shares purchasable upon the
exercise of this Warrant shall be changed to the number determined by dividing
(i) an amount equal to the number of shares issuable upon the exercise of


                                        - 3 -
<PAGE>

this Warrant immediately prior to such adjustment, multiplied by the Purchase
Price in effect immediately prior to such adjustment, by (ii) the Purchase Price
in effect immediately after such adjustment.

              (d)    ADJUSTMENTS FOR OTHER DIVIDENDS AND DISTRIBUTIONS.  In the
event the Company at any time or from time to time after the Original Issue Date
shall make or issue, or fix a record date for the determination of holders of
Common Stock entitled to receive, a dividend or other distribution payable in
securities of the Company (other than shares of Common Stock) or in cash or
other property (other than cash out of earnings or earned surplus, determined in
accordance with generally accepted accounting principles), then and in each such
event provision shall be made so that the Registered Holder shall receive upon
exercise hereof, in addition to the number of shares of Common Stock issuable
hereunder, the kind and amount of securities of the Company and/or cash and
other property which the Registered Holder would have been entitled to receive
had this Warrant been exercised into Common Stock on the date of such event and
had the Registered Holder thereafter, during the period from the date of such
event to and including the Exercise Date, retained any such securities
receivable, giving application to all adjustments called for during such period
under this Section 2 with respect to the rights of the Registered Holder.

              (e)    ADJUSTMENT FOR MERGERS OR REORGANIZATIONS, ETC.  If there
shall occur any reorganization, recapitalization, consolidation or merger
involving the Company in which the Common Stock is converted into or exchanged
for securities, cash or other property (other than a transaction covered by
subsections 2(a), 2(b) or 2(d)), then, following any such reorganization,
recapitalization, consolidation or merger, the Registered Holder shall receive
upon exercise hereof the kind and amount of securities, cash or other property
which the Registered Holder would have been entitled to receive if, immediately
prior to such reorganization, recapitalization, consolidation or merger, the
Registered Holder had held the number of shares of Common Stock subject to this
Warrant.  In any such case, appropriate adjustment (as determined in good faith
by the Board of Directors of the Company) shall be made in the application of
the provisions set forth herein with respect to the rights and interests
thereafter of the Registered Holder, to the end that the provisions set forth in
this Section 2 (including provisions with respect to changes in and other
adjustments of the Purchase Price) shall thereafter be applicable, as nearly as
reasonably may be, in relation to any securities, cash or other property
thereafter deliverable upon the exercise of this Warrant.

              (f)    CERTIFICATE AS TO ADJUSTMENTS.  Upon the occurrence of each
adjustment or readjustment of the Purchase Price pursuant to this Section 2, the
Company at its expense shall promptly compute such adjustment or readjustment in
accordance with the terms hereof and furnish to the Registered Holder a
certificate setting forth such adjustment or readjustment (including the kind
and amount of securities, cash or other property for which this Warrant shall be
exercisable and the Purchase Price) and showing in detail the facts upon which
such adjustment or readjustment is based.  The Company shall, upon the written
request at any time of the Registered Holder, furnish or cause to be furnished
to the Registered Holder a certificate setting forth (i) the Purchase Price then
in effect and (ii) the number of shares of Common Stock and the amount, if any,
of other securities, cash or property which then would be received upon the
exercise of this Warrant.


                                        - 4 -
<PAGE>

       3.     FRACTIONAL SHARES.  The Company shall not be required upon the
exercise of this Warrant to issue any fractional shares, but shall make an
adjustment therefor in cash on the basis of the Fair Market Value per share of
Common Stock, as determined pursuant to subsection 1(b) above.

       4.     REQUIREMENTS FOR TRANSFER.

              (a)    This Warrant and the Warrant Shares shall not be sold or
transferred unless either (i) they first shall have been registered under the
Securities Act of 1933, as amended (the "Act"), or (ii) the Company first shall
have been furnished with an opinion of legal counsel, reasonably satisfactory to
the Company, to the effect that such sale or transfer is exempt from the
registration requirements of the Act.

              (b)    Notwithstanding the foregoing, no registration or opinion
of counsel shall be required for (i) a transfer by a Registered Holder which is
a corporation to a wholly owned subsidiary of such corporation, or to a
corporation which wholly owns such Registered Holder (a "Parent Corporation") or
which is wholly owned by such Parent Corporation, a transfer by a Registered
Holder which is a partnership to a partner of such partnership or a retired
partner of such partnership or to the estate of any such partner or retired
partner, or a transfer by a Registered Holder which is a limited liability
company to a member of such limited liability company or a retired member or to
the estate of any such member or retired member, provided that the transferee in
each case agrees in writing to be subject to the terms of this Section 4, or
(ii) a transfer made in accordance with Rule 144 under the Act.

              (c)    Each certificate representing Warrant Shares shall bear a
legend substantially in the following form:

                     "The securities represented by this
                     certificate have not been registered
                     under the Securities Act of 1933, as
                     amended, and may not be offered, sold
                     or otherwise transferred, pledged or
                     hypothecated unless and until such
                     securities are registered under such
                     Act or an opinion of counsel
                     satisfactory to the Company is
                     obtained to the effect that such
                     registration is not required."

       The foregoing legend shall be removed from the certificates representing
any Warrant Shares, at the request of the holder thereof, at such time as they
become eligible for resale pursuant to Rule 144(k) under the Act.

              (d)    The Company hereby represents and warrants to the
Registered Holder that when issued in accordance with the terms hereof, the
Warrant Shares will be fully paid and non-assessable and free and clear of all
liens, encumbrances and restrictions except as imposed by applicable federal and
state securities laws.

       5.     NO IMPAIRMENT.  The Company will not, by amendment of its charter
or through reorganization, transfer of assets, consolidation, merger,
dissolution, issue or sale of securities or any other voluntary action, avoid or
seek to avoid the observance or performance of any of the


                                        - 5 -
<PAGE>

terms of this Warrant, but will at all times in good faith assist in the
carrying out of all such terms and in the taking of all such action as may be
necessary or appropriate in order to protect the rights of the holder of this
Warrant against impairment.

       6.     NOTICES OF RECORD DATE, ETC.  In the event:

              (a)    the Company shall take a record of the holders of its
Common Stock (or other stock or securities at the time deliverable upon the
exercise of this Warrant) for the purpose of entitling or enabling them to
receive any dividend or other distribution, or to receive any right to subscribe
for or purchase any shares of stock of any class or any other securities, or to
receive any other right; or

              (b)    of any capital reorganization of the Company, any
reclassification of the Common Stock of the Company, any consolidation or merger
of the Company with or into another corporation (other than a consolidation or
merger in which the Company is the surviving entity and its Common Stock is not
converted into or exchanged for any other securities or property), or any
transfer of all or substantially all of the assets of the Company; or

              (c)    of the voluntary or involuntary dissolution, liquidation or
winding-up of the Company, then, and in each such case, the Company will mail or
cause to be mailed to the Registered Holder a notice specifying, as the case may
be, (i) the record date for such dividend, distribution or right, and the amount
and character of such dividend, distribution or right, or (ii) the effective
date on which such reorganization, reclassification, consolidation, merger,
transfer, dissolution, liquidation or winding-up is to take place, and the time,
if any is to be fixed, as of which the holders of record of Common Stock (or
such other stock or securities at the time deliverable upon the exercise of this
Warrant) shall be entitled to exchange their shares of Common Stock (or such
other stock or securities) for securities or other property deliverable upon
such reorganization, reclassification, consolidation, merger, transfer,
dissolution, liquidation or winding-up.  Such notice shall be mailed at least
ten days prior to the record date or effective date for the event specified in
such notice; provided that the failure to give such notice shall not invalidate
any such event or action or give the Registered Holder the right to enjoin or
otherwise stop such event or action.

       7.     RESERVATION OF STOCK.  The Company will at all times reserve and
keep available, solely for issuance and delivery upon the exercise of this
Warrant, such number of Warrant Shares and other securities, cash and/or
property, as from time to time shall be issuable upon the exercise of this
Warrant.

       8.     EXCHANGE OF WARRANTS.  Upon the surrender by the Registered
Holder, properly endorsed, to the Company at the principal office of the
Company, the Company will, subject to the provisions of Section 4 hereof, issue
and deliver to or upon the order of such Holder, at the Company's expense, a new
Warrant or Warrants of like tenor, in the name of the Registered Holder or as
the Registered Holder (upon payment by the Registered Holder of any applicable
transfer taxes) may direct, calling in the aggregate on the face or faces
thereof for the number of shares of Common Stock (or other securities, cash
and/or property) then issuable upon exercise of this Warrant.


                                        - 6 -
<PAGE>

       9.     REPLACEMENT OF WARRANTS.  Upon receipt of evidence reasonably
satisfactory to the Company of the loss, theft, destruction or mutilation of
this Warrant and (in the case of loss, theft or destruction) upon delivery of an
indemnity agreement (with surety if reasonably required) in an amount reasonably
satisfactory to the Company, or (in the case of mutilation) upon surrender and
cancellation of this Warrant, the Company will issue, in lieu thereof, a new
Warrant of like tenor.

       10.    TRANSFERS, ETC.

              (a)    The Company will maintain a register containing the name
and address of the Registered Holder of this Warrant.  The Registered Holder may
change its or his address as shown on the warrant register by written notice to
the Company requesting such change.

              (b)    Subject to the provisions of Section 4 hereof, this Warrant
and all rights hereunder are transferable, in whole or in part, upon surrender
of this Warrant with a properly executed assignment (in the form of EXHIBIT II
hereto) at the principal office of the Company.

              (c)    Until any transfer of this Warrant is made in the warrant
register, the Company may treat the Registered Holder as the absolute owner
hereof for all purposes; PROVIDED, HOWEVER, that if and when this Warrant is
properly assigned in blank, the Company may (but shall not be obligated to)
treat the bearer hereof as the absolute owner hereof for all purposes,
notwithstanding any notice to the contrary.

       11.    MAILING OF NOTICES, ETC.  All notices and other communications
from the Company to the Registered Holder shall be mailed by first-class
certified or registered mail, postage prepaid, to the address last furnished to
the Company in writing by the Registered Holder.  In addition, unless the
Registered Holder otherwise instructs the Company in writing, copies of all
notices to the Registered Holder shall be sent to Silicon Valley Bank, Treasury
Department, 303 Tasman Drive, MS NC 821, Santa Clara, CA 95054.  All notices and
other communications from the Registered Holder or in connection herewith to the
Company shall be mailed by first-class certified or registered mail, postage
prepaid, to the Company at its principal office set forth below.  If the Company
should at any time change the location of its principal office to a place other
than as set forth below, it shall give prompt written notice to the Registered
Holder and thereafter all references in this Warrant to the location of its
principal office at the particular time shall be as so specified in such notice.

       12.    NO RIGHTS AS STOCKHOLDER.  Until the exercise of this Warrant, the
Registered Holder shall not have or exercise any rights by virtue hereof as a
stockholder of the Company.  Notwithstanding the foregoing, in the event (i) the
Company effects a split of the Common Stock by means of a stock dividend and the
Purchase Price of and the number of Warrant Shares are adjusted as of the date
of the distribution of the dividend (rather than as of the record date for such
dividend), and (ii) the Registered Holder exercises this Warrant between the
record date and the distribution date for such stock dividend, the Registered
Holder shall be entitled to receive, on the distribution date, the stock
dividend with respect to the shares of Common Stock acquired upon such exercise,
notwithstanding the fact that such shares were not outstanding as of the close
of business on the record date for such stock dividend.


                                        - 7 -
<PAGE>

       13.    CHANGE OR WAIVER.  Any term of this Warrant may be changed or
waived only by an instrument in writing signed by the party against which
enforcement of the change or waiver is sought.

       14.    SECTION HEADINGS.  The section headings in this Warrant are for
the convenience of the parties and in no way alter, modify, amend, limit or
restrict the contractual obligations of the parties.

       15.    GOVERNING LAW.  This Warrant will be governed by and construed in
accordance with the internal laws of the State of Delaware (without reference to
the conflicts of law provisions thereof).

       16.    REGISTRATION RIGHTS AGREEMENT.  The Registered Holder is entitled
to the rights, and subject to the obligations set forth in the Amended and
Restated Registration Rights Agreement dated December 30, 1999, among the
Company and the stockholders named therein, as it may be amended from time to
time (the "Registration Rights Agreement").  Without limiting the foregoing, by
its acceptance of this Warrant, the Registered Holder, and any other holder of
this Warrant, agrees to be subject to the provisions of Section 4 of the
Registration Rights Agreement (the "Holdback Agreement").  The Registered Holder
shall not be bound by any amendment to the Registration Rights Agreement which
would adversely affect the Registered Holder without the Registered Holder's
written consent unless such amendment affects all Investors thereunder in a
similar manner.

       EXECUTED as of the Date of Issuance indicated above.

                                          I-many, Inc.

                                          By:  /s/ Philip M. St. Germain
                                             --------------------------------
                                                   Philip M. St. Germain
[Corporate Seal]                          Title:  CFO
                                                -----------------------------
ATTEST:

 /s/ Carol A. Ruymos
----------------------------


                                        - 8 -

<PAGE>

                                                                       EXHIBIT I

                                    PURCHASE FORM

To:_________________                                          Dated:____________

       The undersigned, pursuant to the provisions set forth in the attached
Warrant (No. ___), hereby irrevocably elects to purchase (CHECK APPLICABLE BOX):

       / /    _____ shares of the Common Stock covered by such Warrant; or

       / /    the maximum number of shares of Common Stock covered by such
              Warrant pursuant to the cashless exercise procedure set forth in
              Section 1(b).

       The undersigned herewith makes payment of the full purchase price for
such shares at the price per share provided for in such Warrant, which is
$________.  Such payment takes the form of (CHECK APPLICABLE BOX OR BOXES):

       / /    $______ in lawful money of the United States; and/or

       / /    the cancellation of such portion of the attached Warrant as is
              exercisable for a total of _____ Warrant Shares (using a Fair
              Market Value of $_____ per share for purposes of this
              calculation); and/or

       / /    the cancellation of such number of Warrant Shares as is necessary,
              in accordance with the formula set forth in Section 1(b), to
              exercise this Warrant with respect to the maximum number of
              Warrant Shares purchasable pursuant to the cashless exercise
              procedure set forth in Section 1(b).

                                          SILICON VALLEY BANK

                                          By:
                                                 ----------------------------

                                          Its:
                                                 ----------------------------

                                                 ----------------------------


                                        - 9 -
<PAGE>

                                                                      EXHIBIT II

                                   ASSIGNMENT FORM

       FOR VALUE RECEIVED, ________________________________________ hereby
sells, assigns and transfers all of the rights of the undersigned under the
attached Warrant (No. ____) with respect to the number of shares of Common Stock
covered thereby set forth below, unto:


Name of Assignee                   Address                     No. of Shares
----------------                   -------                     -------------



Dated:                                    Signature:
      ---------------------                         -------------------------
Signature Guaranteed:

By:
   ------------------------

The signature should be guaranteed by an eligible guarantor institution (banks,
stockbrokers, savings and loan associations and credit unions with membership in
an approved signature guarantee medallion program) pursuant to Rule 17Ad-15
under the Securities Exchange Act of 1934.


                                        - 10 -