Trifluoroacetic acid methylene chloride → HCID 178504710, compound

HRID 1987073Notes

Reaction equation

HRID 1987073 reaction equation
C(Cl)Cl.C(O)(C(F)(F)F)=O.C(OC([N:18]=[C:19]([N:21](C(OC(C)(C)C)=O)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:52])[CH2:27][C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[C:30]([NH:36][CH2:37][C:38]([F:50])([F:49])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[S:45]([CH3:48])(=[O:47])=[O:46])[C:29]=1[F:51])[NH2:20])=O)(C)(C)C>>[C:19]([NH:21][O:22][CH2:23][CH2:24][NH:25][C:26](=[O:52])[CH2:27][C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[C:30]([NH:36][CH2:37][C:38]([F:49])([F:50])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[S:45]([CH3:48])(=[O:47])=[O:46])[C:29]=1[F:51])(=[NH:18])[NH2:20]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86595389HCID 86595389, compound

Product 1

HCID 178504710HCID 178504710, compoundYield 74%

Procedure

A solution of 3:1 CH2Cl2/TFA (0.8 mL) was added to N-[2-(N′,N″-bis(tert-butoxycarbonyl)amidinoaminooxy)ethyl]-2-{3-[(2,2-difluoro-2-(2 methanesulfonylphenyl)ethyl)amino]-6-cyano-2-fluorophenyl}acetamide (34.8 mg, 0.049 mmol)(prepared essentially as described in Example 2h), and the reaction mixture was stirred at room temperature for 3 h. After evaporating the solvents, the residue was subjected to flash chromatography (DCM/MeOH saturated with gaseous NH3; 95:5→90:10) to yield 18.4 mg (74%) of the title compound as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.24 (m, 1H), 7.74 (m, 3H), 7.20 (dd, J=8.6 Hz, 1.3 Hz, 1H), 6.87 (t, J=8.7 Hz, 1H), 4.24 (t, J=14.2 Hz, 2H), 3.80 (t, J=5.2 Hz, 2H), 3.72 (d, J=1.9 Hz, 2H), 3.43 (t, J=5.5 Hz, 2H), 3.27 (s, 3H). LC/MS (m/z) [M+1]+ 513.4 (calculated for C21H24F3N6O4S, 513.5).

Workup

  1. customprepared essentially
  2. customAfter evaporating the solvents

Sources & evidence

ORD record
ord-887f1bbbda664a71908b84bd6c2433a8
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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