5163-19-9 → HCID 68413344, compound

HRID 1879987Notes

Reaction equation

HRID 1879987 reaction equation
[Br:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7](=O)[CH2:8][N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1.CN1CC2C=CC=CC=2NCC1>>[BrH:1].[Br:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][CH2:7][CH2:8][N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 3987075163-19-9HCID 59456946HCID 59456946, compound

Product 1

HCID 68413344HCID 68413344, compound

Procedure

7-bromo-4-methyl-1,3,4,5-tetrahydro-pyrido[e][1,4]diazepin-2-one (1.67 g, 6.55 mmol) was reduced to give a 1:1 mixture of the title compound and 4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine. The mixture was dissolved in acetic acid (12 mL), treated with bromine (1.04 g, 6.5 mmol) and stirred at room temperature overnight. Ether (100 mL) was added and the precipitate was isolated by filtration to yield the title compound as an orange solid (2.04 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 10.23 (s, 1H) 8.16 (d, J=2.3 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 6.89 (s, 1H), 4.25-4.48 (m, 2H), 3.54-3.58 (m, 2H), 3.28-3.35 (m, 2H), 2.86-2.87 (m, 3H); MS (ESI) m/e 242 (C9H12BrN3+H)+.

Workup

  1. customto give

Sources & evidence

ORD record
ord-f3d2f9e7f2b3491e84b609bc5b732ba7
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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