N-Methyl-3-phenylpropan-1-amine → 4-Methyl-2-{6-[methyl-(3-phenyl-propyl)-amino]-pyrazin-2-yl}-thiazole-5-carboxylic acid 4-fluoro-benzylamide

HRID 1879158Notes

Reaction equation

HRID 1879158 reaction equation
FC1C=CC(CNC)=CC=1.[CH3:11][NH:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:22][C:23]1[CH:45]=[CH:44][C:26]([CH2:27][NH:28][C:29]([C:31]2[S:35][C:34]([C:36]3[CH:41]=[N:40][CH:39]=[C:38](I)[N:37]=3)=[N:33][C:32]=2[CH3:43])=[O:30])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:45]=[CH:44][C:26]([CH2:27][NH:28][C:29]([C:31]2[S:35][C:34]([C:36]3[CH:41]=[N:40][CH:39]=[C:38]([N:12]([CH3:11])[CH2:13][CH2:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:37]=3)=[N:33][C:32]=2[CH3:43])=[O:30])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 35417N-Methyl-3-phenylpropan-1-amineHCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 866455582-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide

Product 1

HCID 249547024-Methyl-2-{6-[methyl-(3-phenyl-propyl)-amino]-pyrazin-2-yl}-thiazole-5-carboxylic acid 4-fluoro-benzylamideYield 70%

Procedure

Following the procedure described in Example 14, making variations as required to replace 4-fluoro-N-methyl-benzylamine with methyl-(3-phenyl-propyl)-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 70% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.49 (s, 1H), 7.99 (s, 1H), 7.31-7.38 (m, 2H), 7.09-7.28 (m, 5H), 7.00-7.08 (m, 2H), 6.17 (bs, 1H), 4.56 (d, J=8.0 Hz, 2H), 3.57-3.64 (m, 2H), 3.10 (s, 3H), 2.69 (s, 3H), 2.64-2.71 (m, 2H), 1.91-2.01 (m, 2H); MS (ES+) m/z 476.2 (M+1), Rt=1.69 min.

Sources & evidence

ORD record
ord-1907c3ca6797472d9b8f4483e7d54448
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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