Trifluoroacetic acid → HCID 24764746, compound

HRID 1172899Notes

Reaction equation

HRID 1172899 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:20]([C:22]1[S:26][C:25]2[CH:27]=[C:28]([CH:31]([C:33](=[O:35])[NH2:34])[F:32])[CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:20]([C:22]1[S:26][C:25]2[CH:27]=[C:28]([CH:31]([C:33](=[O:35])[NH2:34])[F:32])[CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68694547HCID 68694547, compound

Product 1

HCID 24764746HCID 24764746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-{[6-(carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carbonyl]-amino}-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (163 mg, 0.31 mmol)) in methylene chloride (2 mL) was added trifluoroacetic acid (1 mL) and the solution was stirred at ambient temperature for 16 hours. The reaction was evaporated to dryness. The residue was washed with sat. NaHCO3 and MeOH, and the solid was filtered. 1H NMR (DMSO-d6) δ 10.03 (br s, 1H), 8.33 (s, 1H), 8.11 (s, 1H), 8.02 (d, J=8.2 Hz, 1H), 7.93 (s, 1H), 7.62 (br d, J=2.4 Hz, 1H), 7.51 (d, J=8.2 Hz, 1H), 7.45 (d, J=1.8 Hz, 1H), 7.33 (dd, J=5.0, 1.8 Hz, 1H), 7.29 (dd, J=8.2, 1.8 Hz, 1H), 7.23 (dd, J=3.5, 1.8 Hz, 1H), 7.02 (dd, J=5.2, 3.5 Hz, 1H), 6.79 (d, J=8.2 Hz, 1H), 5.93 (d, J=45.7 Hz, 1H), 5.24 (s, 2H). cal'd 427 (MH+), exp 427 (MH+).

Workup

  1. customThe reaction was evaporated to dryness
  2. washThe residue was washed with sat. NaHCO3 and MeOH
  3. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-81b35effea644de08f1d37298399569e
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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