HCID 10387575, compound → HCID 10339368, compound

HRID 2221480Notes

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](O)=[O:15])[CH:13]=[C:8]2[C:7]([CH2:17][N:18]([CH3:20])[CH3:19])=[CH:6]1.C(OCC1C2C(=CN=C([C:44]([NH:46][OH:47])=O)C=2)N(CC2C=CC(F)=CC=2F)C=1)C1C=CC=CC=1>>[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:46]([OH:47])[CH3:44])=[O:15])[CH:13]=[C:8]2[C:7]([CH2:17][N:18]([CH3:20])[CH3:19])=[CH:6]1

Participants

Reactant 2

HCID 10387575HCID 10387575, compound

HCID 21892247HCID 21892247, compound

Product 1

HCID 10339368HCID 10339368, compound

Procedure

1-(2,4-Difluorobenzyl)-3-dimethylaminomethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(2,4-difluorobenzyl)-3-dimethylaminomethyl-1H-pyrrolo[2,3]-ccarboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6) δ: 8.91 (s, 1H), 8.43 (s, 1H), 7.74 (s, 1H), 7.29-7.37 (m, 2H), 7.04-7.10 (m, 1H), 5.62 (s, 2H), 3.70 (s, 2H), 2.22 (s, 6H). LCMS (API-ES, M+H+): 346.3. (b) 1-(2,4-Difluorobenzyl)-3-dimethylaminomethyl-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- dimethylaminomethyl-1H-pyrrol (DMSO-d6)δ: 9.44 (broad s, 1H), 8.96 (s, 1H), 8.26 (s, 1H), 7.93 (s, 1H), 7.44 (m, 1H), 7.28-7.35 (m, 1H), 7.10 (m, 1H), 5.66 (s, 2H), 4.47 (s, 2H), 3.32 (s, 3H), 2.72 (s, 6H). LCMS (APCI, M+H+): 375.0. HRMS calcd for C19H21F2N4O2. (M+H) 375.1633, found 375.1632. HPLC: 97.62% purity.

Sources & evidence

ORD record: ord-4df7d81468174290a754f078054a9697
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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