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

HRID 1062127Notes

Reaction equation

HRID 1062127 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][CH:19]=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH:22][C:23](=[O:35])[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[CH:28]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:35]=[C:23]1[CH2:24][C:25]([C:27]2[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=2)[C:33]#[N:34])=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][C:9]=2[NH:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11167526{2-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-phenylethynyl-phenyl}-carbamic acid tert.-butyl ester

Product 1

HCID 98203213-(4-Oxo-7-phenylethynyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrileYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from {2-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-4-phenylethynyl-phenyl}-carbamic acid tert.-butyl ester (Example K2) (230 mg, 0.48 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (135 mg).

Sources & evidence

ORD record
ord-6421269797f9472fa9c7949718587b6e
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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