N-methylhydroxylamine hydrochloride → 1-(2,4-Difluorobenzyl)-N-hydroxy-N-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2221470Notes

Reaction equation

HRID 2221470 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([OH:16])=O)[CH:13]=[C:8]2[CH:7]=[CH:6]1.Cl.[CH3:23][NH:24][OH:25]>>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([N:24]([OH:25])[CH3:23])=[O:16])[CH:13]=[C:8]2[CH:7]=[CH:6]1

Participants

3

Reactant 2

HCID 77906N-methylhydroxylamine hydrochlorideHCID 218922121-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 100643901-(2,4-Difluorobenzyl)-N-hydroxy-N-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Procedure

The title compound was prepared by coupling of 1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid and N-methyl hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) δ: 11.10 (br, 1H), 8.92 (s, 1H), 8.04 (s, 1H), 7.82 (s, 1H), 7.26-7.38 (m, 2H), 7.07-7.08 (m, 1H), 6.72 (s, 1H), 5.64 (s, 2H), 3.33 (s, 3H). LCMS (API-ES, M+H+): 318.0. HRMS calcd for C16H14F2N3O2(M+H) 318.1054, found 318.1037. HPLC: 100% purity.

Sources & evidence

ORD record
ord-413c09cf36c54064bf891f1bc6ab56a3
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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