Sodium Methoxide → HCID 67263794, compound

HRID 1041808Notes

Reaction equation

HRID 1041808 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([C:15](=[O:17])[CH3:16])[C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[C:13]#[N:14].C[O-].[Na+]>[Ni].C(Cl)Cl.CO>[C:15]([N:5]1[C:6]2[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=2[CH2:13][NH:14][C:3](=[O:2])[CH2:4]1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67264115HCID 67264115, compound

Product 1

HCID 67263794HCID 67263794, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of [acetyl-(5-amino-2-cyano-phenyl)-amino]-acetic acid methyl ester (0.4 g, 1.6 mmol), sodium methoxide (87 mg, 1.6 mmol) and Raney nickel (50 mg) was shaken for 12 hours under a 50 psi H2 atmosphere. The catalyst was removed by filtration and the filtrate was concentrated. Silica gel chromatography (DCM/MeOH 9:1) gave 1-acetyl-8-amino-1,2,4,5-tetrahydro-benzo[e][1,4]diazepin-3-one (120 mg, 0.55 mmol, 34%): 1H NMR (300 MHz, CD3OD) δ 7.12 (d, 1H), 6.7 (m, 2H), 5.35 (d, 1H), 4.37 (d, 1H), 3.80 (d, 1H), 3.49 (d, 1H), 1.93 (s, 3H);); MS (m/e) 220 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b32a4dc2965e485ea7493a7f9dcfc214
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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