5163-19-9 → HCID 68413344, compound

HRID 340837Notes

Reaction equation

HRID 340837 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) δ10.23 (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-14bf2d021858496785f561f1e6b76fd2
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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