Trifluoroacetic acid → HCID 56601381, compound

HRID 1619606Notes

Reaction equation

HRID 1619606 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:33]3[S:34][CH:35]=[CH:36][N:37]=3)(=[O:31])=[O:30])=[CH:25][C:24]=2[C:38]#[N:39])=[C:18]([C:40]2[N:44]([CH3:45])[N:43]=[CH:42][CH:41]=2)[CH:17]=1)C)(C)(C)C.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>ClCCl>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[C:38]([C:24]1[CH:25]=[C:26]([S:29]([NH:32][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)(=[O:30])=[O:31])[CH:27]=[CH:28][C:23]=1[O:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][NH:7][CH3:6])=[CH:17][C:18]=1[C:40]1[N:44]([CH3:45])[N:43]=[CH:42][CH:41]=1)#[N:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87277520HCID 87277520, compound

Product 1

HCID 56601381HCID 56601381, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-{[4′-{2-cyano-4-[(1,3-thiazol-2-ylamino)sulfonyl]phenoxy}-3′(1-methyl-1H-pyrazol-5-yl)biphenyl-2-yl]methyl}methylcarbamate (Preparation 65, 64 mg, 0.01 mmol) was dissolved in dichloromethane (5 mL), trifluoroacetic acid (0.2 mL) was added and the reaction was stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC to afford the title compound (22 mg, 37%) as a white solid as the trifluoroacetate salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-f68e8f13c8724c0aa47765bcb39b6896
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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