O-Methylhydroxylamine hydrochloride → 1-(2,4-Difluorobenzyl)-N-methoxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 720534Notes

Reaction equation

HRID 720534 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](O)=[O:15])[CH:13]=[C:8]2[CH:7]=[CH:6]1.Cl.[CH3:23][O:24][NH2:25]>>[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]([NH:25][O:24][CH3:23])=[O:15])[CH:13]=[C:8]2[CH:7]=[CH:6]1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 218922121-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 103811051-(2,4-Difluorobenzyl)-N-methoxy-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 O-methyl hydroxylamine hydrochloride in analogy to step (c) of example 1. 1H NMR (CD3OD) δ; 8.80 (s, 1H), 8.33 (s, 1H), 7.64 (d, 1H, J=3.0 Hz), 7.24–7.27 (m, 1H), 6.96–7.08 (m, 2H), 6.74 (d, 1H, J=3.0 Hz), 5.62 (s, 2H) 3.85 (s, 3H). LCMS (API-ES, M+H+): 318.0. HRMS calcd for C16H14F2N3O2. (M+H) 318.1054. found 318.1045. Anal. (C16H13F2N3O2) C, H, N. HPLC: 99.6% purity.

Sources & evidence

ORD record
ord-d335b7c72f1549a6b40bf6e1fddad88a
Source dataset
uspto-grants-2006_11
Patent number
US07135482B2

Reaction notes

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