Trifluoroacetic acid → 3-[4-Oxo-7-(4-trifluoromethoxy-phenylethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile

HRID 859518Notes

Reaction equation

HRID 859518 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH:27][C:28](=[O:40])[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:40]=[C:28]1[CH2:29][C:30]([C:32]2[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=2)[C:38]#[N:39])=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=3)=[CH:10][C:9]=2[NH:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588017[2-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-(4-trifluoromethoxy-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester

Product 1

HCID 222248123-[4-Oxo-7-(4-trifluoromethoxy-phenylethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrileYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from [2-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-4-(4-trifluoromethoxy-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester (Example K30) (170 mg, 0.3 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a beige solid (112 mg).

Sources & evidence

ORD record
ord-3fa68fc111554274ac819333bf01757b
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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