N-methylhydroxylamine hydrochloride → HCID 11740168, compound

HRID 2221478Notes

Reaction equation

HRID 2221478 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([OH:16])=O)[CH:13]=[C:8]2[C:7]([CH2:17][O:18][CH2:19][CH3:20])=[CH:6]1.FC1C=C(F)C=CC=1CN1C2=CN=C(C(OCC)=O)C=C2C(COCC)=C1.C(OCC1C2C(=CN=C([C:71]([NH:73][OH:74])=O)C=2)N(CC2C=CC(F)=CC=2F)C=1)C1C=CC=CC=1.Cl.CNO>>[F:1][C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([N:73]([OH:74])[CH3:71])=[O:16])[CH:13]=[C:8]2[C:7]([CH2:17][O:18][CH2:19][CH3:20])=[CH:6]1

Participants

5

Reactant 4

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10387575HCID 10387575, compoundHCID 21892193HCID 21892193, compound2×HCID 21892237HCID 21892237, compound

Product 1

HCID 11740168HCID 11740168, compound

Procedure

1-(2,4-Difluorobenzyl)-3-ethoxymethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(2,4-difluorobenzyl)-3-ethoxymethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6). δ: 8.96 (s, 1H), 8.34 (s, 1H), 7.78 (s, 1H), 7.08-7.40 (m, 2H), 7.07 (m, 1H), 5.62 (s, 2H), 4.63 (s, 2H), 3.48 (q, 2H, J=7.0 Hz), 1.11 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 347.0. (b) 1-(2,4-Difluorobenzyl)-3-ethoxymethyl-N-hydroxy-N-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(2,4-difluorobenzyl)-3-ethoxymethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid and N-methyl hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (CD3OD) δ: 8.81 (s, 1H), 8.27 (s, 1H), 7.71 (s, 1H), 7.29 -7.30 (m, 1H), 6.98 -7.30 (m, 2H), 5.58 (s, 2H), 4.72 (s, 2H), 3.59 (q, 2H, J=7.0 Hz), 3.43 (s, 3H), 1.20 (t, 3H, J=7.0 Hz). LCMS (APCI, M+H+): 376.1. HRMS calcd for C19H20F2N3O3 (M+H) 376.1473, found 376.1454. Anal. (C19H19F2N3O3×0.2H2O) C, H, N. HPLC: 100% purity.

Sources & evidence

ORD record
ord-6268034ddb324bc0a759f6c3efb2f05b
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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