Betahistine → HCID 24955066, compound

HRID 1879161Notes

Reaction equation

HRID 1879161 reaction equation
FC1C=CC(CNC)=CC=1.[CH3:11][NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[F:21][C:22]1[CH:44]=[CH:43][C:25]([CH2:26][NH:27][C:28]([C:30]2[S:34][C:33]([C:35]3[CH:40]=[N:39][CH:38]=[C:37](I)[N:36]=3)=[N:32][C:31]=2[CH3:42])=[O:29])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:44]=[CH:43][C:25]([CH2:26][NH:27][C:28]([C:30]2[S:34][C:33]([C:35]3[CH:40]=[N:39][CH:38]=[C:37]([N:12]([CH3:11])[CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[N:36]=3)=[N:32][C:31]=2[CH3:42])=[O:29])=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 2366BetahistineHCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 866455582-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide

Product 1

HCID 24955066HCID 24955066, compoundYield 75%

Procedure

Following the procedure described in Example 14, making variations as required to replace 4-fluoro-N-methyl-benzylamine with methyl-(2-pyridin-2-yl-ethyl)-amine to react with 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide, the title compound was obtained in 75% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.40-8.52 (m, 2H), 8.03 (s, 1H), 7.36-7.43 (m, 3H), 7.11-7.35 (m, 3H), 7.00-7.10 (m, 2H), 4.55 (d, J=4.0 Hz, 2H), 4.00-4.15 (m, 2H), 3.15-3.40 (m, 2H), 3.12 (bs, 3H), 2.70 (s, 3H); MS (ES+) m/z 463.1 (M+1), Rt=1.39 min.

Sources & evidence

ORD record
ord-6152b6f7e509426cb949e24d7b0ba44b
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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