tert-Butyl (2-amino-4-chloro-5-methylphenyl)carbamate → 8-Chloro-7-methyl-4-(3-pyrimidin-2-yl-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 498806Notes

Reaction equation

HRID 498806 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([Cl:15])=[CH:10][C:9]=1[NH2:16])(C)(C)C.C(O[C:23](=[O:39])[CH2:24][C:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[N:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:27]=1)(C)(C)C>>[Cl:15][C:11]1[C:12]([CH3:14])=[CH:13][C:8]2[N:7]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]4[N:33]=[CH:34][CH:35]=[CH:36][N:37]=4)[CH:27]=3)[CH2:24][C:23](=[O:39])[NH:16][C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 69486983tert-Butyl (2-amino-4-chloro-5-methylphenyl)carbamateHCID 694873573-Oxo-3-(3-pyrimidin-2-yl-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 223180368-Chloro-7-methyl-4-(3-pyrimidin-2-yl-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from (2-amino-4-chloro-5-methyl-phenyl)-carbamic acid tert-butyl ester (Example J22) (128 mg, 0.5 mmol) and 3-oxo-3-(3-pyrimidin-2-yl-phenyl)-propionic acid tert-butyl ester (Example K44) (179 mg, 0.6 mmol) according to the general procedure M and subsequent treatment of the crude product according to the general procedure N. Obtained as a light yellow solid (81 mg).

Sources & evidence

ORD record
ord-ab63f4277ea948bebf1a4df94b19e649
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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