N-benzylhydroxylamine hydrochloride → N-Benzyl-1-(4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 720533Notes

Reaction equation

HRID 720533 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([OH:18])=O)[CH:15]=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[CH2:22]([NH:29][OH:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([N:29]([OH:30])[C:16]([C:14]1[CH:15]=[C:10]2[CH:9]=[CH:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=3)[C:11]2=[CH:12][N:13]=1)=[O:18])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 11332622N-benzylhydroxylamine hydrochlorideHCID 218922071-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 10452086N-Benzyl-1-(4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Procedure

The title compound was prepared by coupling of 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid with N-benzyl hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) δ; 8.92 (s, 1H), 8.11 (s, 1H), 7.91 (d, 1H, J=2.8 Hz), 7.26–7.38 (m, 7H), 7.16 (d, 2H, J=8.5 Hz), 6.72 (d, 1H, J=2.8 Hz), 5,58 (s, 2H), 4.97 (s, 2H). LCMS (API-ES, M+H+): 376.1, HRMS calcd for C22H19FN3O2 (M+H) 376.1461. found 376.1448. Anal. (C22H18FN3O2) C, H, N. HPLC: 100% purity.

Sources & evidence

ORD record
ord-429e161bcd764c0cb6828b3211d53b20
Source dataset
uspto-grants-2006_11
Patent number
US07135482B2

Reaction notes

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