O-Phenylhydroxylamine hydrochloride → 3-(4-Fluorobenzyl)-N-phenoxy-3H-imidazo[4,5-c]pyridine-6-carboxamide

HRID 720539Notes

Reaction equation

HRID 720539 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[N:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[O:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[N:13][C:14]([C:16]([NH:29][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:18])=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 6365179O-Phenylhydroxylamine hydrochlorideHCID 218922273-(4-Fluorobenzyl)-3H-imidazo[4,5-c]pyridine-6-carboxylic acid

Product 1

HCID 100441703-(4-Fluorobenzyl)-N-phenoxy-3H-imidazo[4,5-c]pyridine-6-carboxamide

Procedure

The title compound was prepared by coupling of 3-(4-fluoro-benzyl)-3H-imidazo[4,5-c]pyridine-6-carboxylic acid and N-phenoxyamine hydrochloride under the same conditions as those in step (c) of example 1. 1H NMR (300 MHz, MeOH-d4) δ; 8.82 (s, 1H), 8.53 (s, 1H), 8.43 (s, 1H), 8.24 (d, 2H, J=7.9 Hz), 7.38–7.33 (m, 2H), 7.07–7.01 (m, 2H), 6.88–6.74 (m, 3H), 5.57 (s, 2H). LCMS (API-ES, M+H+): 363.1. HRMS calcd for C20H16FN4O2 (M+H) 363.1257. found 363.1256. HPLC: >85% purity.

Sources & evidence

ORD record
ord-7800d8f1634d4277bfe831c3401b01a9
Source dataset
uspto-grants-2006_11
Patent number
US07135482B2

Reaction notes

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