N-methylhydroxylamine hydrochloride → HCID 9997801, compound

HRID 2221479Notes

Reaction equation

HRID 2221479 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][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][OH:18])=[CH:6]1.FC1C=C(F)C=CC=1CN1C2=CN=C(C(OCC)=O)C=C2C(CO)=C1.C(OCC1C2C(=CN=C([C:67]([NH:69][OH:70])=O)C=2)N(CC2C=CC(F)=CC=2F)C=1)C1C=CC=CC=1.Cl.CNO>>[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([N:69]([OH:70])[CH3:67])=[O:16])[CH:13]=[C:8]2[C:7]([CH2:17][OH:18])=[CH:6]1

Participants

5

Reactant 4

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10387575HCID 10387575, compoundHCID 21892189HCID 21892189, compoundHCID 21892198HCID 21892198, compound2×

Product 1

HCID 9997801HCID 9997801, compound

Procedure

1-(2,4-Difluorobenzyl)-3-hydroxymethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(2,4-difluoro-benzyl)-3-hydroxymethyl-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), 8.41 (s, 1H), 7.69 (s, 1H), 7.29-7.32 (m, 2H), 7.08 (m, 1H), 5.61 (s, 2H), 5.09 (s, 1H), 4.66 (s, 2H). LCMS (API-ES, M+H+): 319.1. (b) 1-(2,4-Difluorobenzyl)-N-hydroxy-3-hydroxymethyl-N-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(2,4-difluoro-benzyl)-3-hydroxymethyl-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: 8.80 (s, 1H), 8.29 (s, 1H), 7.67 (s, 1H), 7.29-7.32 (m, 1H), 6.93-7.04 (m, 2H), 5.57 (s, 2H), 4.81 (s, 2H), 3.43 (s, 3H). LCMS (APCI, M+H+): 348.0. HRMS (M+H): 348.1175; cal: 348.1160 with C17H16F2N3O3. HPLC: 96.15% purity.

Sources & evidence

ORD record
ord-a59160cb6a204bb2b51404701a5b8178
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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