Glycine ethyl ester → (Z)-8-bromo-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 718077Notes

Reaction equation

HRID 718077 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[NH2:17][CH2:18][C:19](OCC)=[O:20]>N1C=CC=CC=1>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2=[C:2]([CH:7]=1)[NH:1][C:19](=[O:20])[CH2:18][N:17]=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 12176Glycine ethyl esterHCID 4149946(2-Amino-4-bromophenyl)(phenyl)methanone

Product 1

HCID 59783468(Z)-8-bromo-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-oneYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2-Amino-4-bromophenyl)(phenyl)methanone (1.75 g, 10 mmol), ethyl 2-aminoacetate (2.23 g, 16 mmol) and pyridine (40 mL) were stirred together at 80° C. for about 3 days. The pyridine was evaporated and the residue was triturated in 5% methanol in ethyl acetate to afford title compound 354 (1.6 g, 51%) as a yellow solid.

Workup

  1. customThe pyridine was evaporated
  2. customthe residue was triturated in 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-3c96ce11ce804a3e84c60e7cff3534e4
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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