4,5-Dichloro-1,2-phenylenediamine → 7,8-Dichloro-4-[3-(2-trifluoromethyl-pyridin-4-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 498743Notes

Reaction equation

HRID 498743 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.C([O:15][C:16](=O)[CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[CH:20]=1)(C)(C)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:16](=[O:15])[CH2:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=4)[CH:20]=3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 792974,5-Dichloro-1,2-phenylenediamineHCID 694868433-Oxo-3-[3-(2-trifluoromethyl-pyridin-4-yl)-phenyl]-propionic acid tert-butyl ester

Product 1

HCID 223173037,8-Dichloro-4-[3-(2-trifluoromethyl-pyridin-4-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The title compound was prepared from commercially available 4,5-dichloro-1,2-phenylendiamine (133 mg, 0.75 mmol) and 3-oxo-3-[3-(2-trifluoromethyl-pyridin-4-yl)-phenyl]-propionic acid tert-butyl ester (Example K38) (274 mg, 0.75 mmol) in xylene (15 ml) under reflux conditions for 2 h according to the general procedure M. Obtained as a light red solid (290 mg, 86%).

Sources & evidence

ORD record
ord-8bd70ddaacab4ea4911233301c046292
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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