N-propylhydroxylamine hydrochloride → 1-[(4-fluorophenyl)methyl]-N-hydroxy-N-propyl-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2377062Notes

Reaction equation

HRID 2377062 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:25][OH:26])[CH2:23][CH3:24]>>[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])[CH2:22][CH2:23][CH3:24])=[O:18])[CH:15]=[C:10]3[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 12355438N-propylhydroxylamine hydrochlorideHCID 218922071-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 115589261-[(4-fluorophenyl)methyl]-N-hydroxy-N-propyl-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-propyl hydroxylamine hydrochloride in a manner similar to step 8 of example 1. 1H NMR (DMSO-d6) δ ppm 11.93 (br s, 1H), 8.88 (s, 1H), 7.99 (s, 1H), 7.88 (d, 1H, J=3.0 Hz), 7.34 (m, 2H), 7.15 (d, 2H, J=8.8 Hz), 6.69 (d, 1H, J=3.0 Hz), 5.56 (s, 2H), 3.66 (t, 2H, J=7.1 Hz), 1.64 (m, 2H), 0.83 (s, 3H). LCMS (API-ES, M+H+): 328.1. HRMS calcd for C18H19FN3O2 (M+H) 328.1456, found 328.1458. HPLC: 100% purity.

Sources & evidence

ORD record
ord-133c9d26ad44478da405b2f72d04bc98
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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