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

HRID 498778Notes

Reaction equation

HRID 498778 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]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[N:27]=2)[CH:21]=1)=O)(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:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[N:27]=4)[CH:21]=3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 792974,5-Dichloro-1,2-phenylenediamineHCID 694867223-[3-(2-Methyl-pyrimidin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

Product 1

HCID 223177577,8-Dichloro-4-[3-(2-methyl-pyrimidin-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 4,5-dichlorophenylenediamine (89 mg 0.5 mmol) and 3-[3-(2-methyl-pyrimidin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester (Example K42) (172 mg, 0.55 mmol) by refluxing in xylene according to the general procedure M. Obtained as a light yellow solid (131 mg).

Sources & evidence

ORD record
ord-8b236765385047b099b37dd28296eee2
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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