N-Isopropylhydroxylamine Hydrochloride → 1-(4-Fluorobenzyl)-N-hydroxy-N-isopropyl-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2377060Notes

Reaction equation

HRID 2377060 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.[CH:22]([NH:25][OH:26])([CH3:24])[CH3:23]>>[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]([N:25]([OH:26])[CH:22]([CH3:24])[CH3:23])=[O:18])[CH:15]=[C:10]3[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 218922071-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 116670201-(4-Fluorobenzyl)-N-hydroxy-N-isopropyl-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-isopropyl hydroxylamine hydrochloride in a manner similar to step 8 of example 1. 1H NMR (CDCl3) δ ppm 8.59 (s, 1H), 8.46 (s, 1H), 7.39 (s, 1H), 7.10 (m, 2H), 7.02 (d, 2H, J=8.6 Hz), 6.73 (s, 1H), 5.41 (s, 2H), 5.08 (m, 1H), 1.33 (d, 6H, J=6.6 Hz). LCMS (APCI, M+H+): 328.1 HRMS calcd for C18H18FN3O2 (M+H) 328.1456, found 328.1456. HPLC: 95.8% purity.

Sources & evidence

ORD record
ord-df3304d45e0342cb9c6f37b027df479d
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

Loading…