Trifluoroacetic acid → (E)-3-(4-oxo-7-(2-(thiazol-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrile

HRID 859491Notes

Reaction equation

HRID 859491 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[CH:10][C:9]=1[NH:21][C:22](=[O:34])[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:34]=[C:22]1[CH2:23][C:24]([C:26]2[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=2)[C:32]#[N:33])=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[CH:10][C:9]=2[NH:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588000{2-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-thiazol-2-ylethynyl-phenyl}-carbamic acid tert.-butyl ester

Product 1

HCID 22224975(E)-3-(4-oxo-7-(2-(thiazol-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrileYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from {2-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-4-thiazol-2-ylethynyl-phenyl}-carbamic acid tert.-butyl ester (Example K11) (119 mg, 0.24 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a yellow solid (36 mg).

Sources & evidence

ORD record
ord-2741c70ec10743c1af2c0cae3115845e
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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