Trifluoroacetic acid → 4-(3-Nitro-phenyl)-8-phenylethynyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 859519Notes

Reaction equation

HRID 859519 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:36])[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:33]([C:29]1[CH:28]=[C:27]([C:25]2[CH2:24][C:23](=[O:36])[NH:22][C:9]3[CH:10]=[C:11]([C:14]#[C:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:32]=[CH:31][CH:30]=1)([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588018{2-[3-(3-Nitro-phenyl)-3-oxo-propionylamino]-4-phenylethynyl-phenyl}-carbamic acid tert.-butyl ester

Product 1

HCID 222249504-(3-Nitro-phenyl)-8-phenylethynyl-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from {2-[3-(3-nitro-phenyl)-3-oxo-propionylamino]-4-phenylethynyl-phenyl}-carbamic acid tert.-butyl ester (Example K31) (970 mg, 1.94 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (631 mg).

Sources & evidence

ORD record
ord-922ec32ff69145c5a39cc5c16416f743
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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