Methylamine → 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methylamide

HRID 470350Notes

Reaction equation

HRID 470350 reaction equation
CO[C:3]([C:5]1[CH:28]=[CH:27][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([C:18]4[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:14][C:13]=3[OH:26])[NH:11][C:7]=2[CH:6]=1)=[O:4].[CH3:29][NH2:30]>>[CH3:29][NH:30][C:3]([C:5]1[CH:28]=[CH:27][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([C:18]4[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:14][C:13]=3[OH:26])[NH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 1361065952-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 1361069462-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methylamideYield 50%

Procedure

A suspension of 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methyl ester (37.5 mg, 0.1 mmol) in aqueous methylamine solution (40%, 2 mL) was heated at 140° C. in a Biotage Initiator Sixty microwave reactor for 15 min, cooled to the room temperature, and concentrated under reduced pressure. The residue was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (19 mg, 50%). 1H NMR (DMSO-d6) δ 2.84 (s, 3H), 3.92 (s, 3H), 7.11-7.17 (2H), 7.62-7.83 (4H), 8.10-8.29 (3H), 8.50 (br, 1H, NH). ESI-MS m/z 375.3 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH)

Sources & evidence

ORD record
ord-3dee2cbda74540fab0c4e70150b61c93
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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