1-(4-fluorophenyl)-N-methylmethanamine → HCID 24955062, compound

HRID 1879157Notes

Reaction equation

HRID 1879157 reaction equation
FC1C=CC(CNC)=CC=1.[CH2:11]([CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:24][C:25]1[CH:47]=[CH:46][C:28]([CH2:29][NH:30][C:31]([C:33]2[S:37][C:36]([C:38]3[CH:43]=[N:42][CH:41]=[C:40](I)[N:39]=3)=[N:35][C:34]=2[CH3:45])=[O:32])=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:47]=[CH:46][C:28]([CH2:29][NH:30][C:31]([C:33]2[S:37][C:36]([C:38]3[CH:43]=[N:42][CH:41]=[C:40]([N:21]4[CH2:22][CH2:23][CH:19]([CH2:11][CH2:12][C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH2:20]4)[N:39]=3)=[N:35][C:34]=2[CH3:45])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 37750123-(2-Phenylethyl)pyrrolidineHCID 866455582-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide

Product 1

HCID 24955062HCID 24955062, compoundYield 75%

Procedure

Following the procedure described in Example 14, making variations as required to replace 4-fluoro-N-methyl-benzylamine with 3-phenethyl-pyrrolidine 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 8.50 (s, 1H), 7.89 (s, 1H), 7.31-7.38 (m, 2H), 7.24-7.30 (m, 2H), 7.14-7.23 (m, 3H), 7.00-7.09 (m, 2H), 6.18 (bs, 1H), 4.55 (d, J=4.0 Hz, 2H), 3.70-3.78 (m, 1H), 3.62-3.69 (m, 1H), 3.39-3.48 (m, 1H), 3.06-3.13 (m, 1H), 2.70 (s, 3H), 2.68-2.75 (m, 2H), 2.27-2.38 (m, 1H), 2.15-2.26 (m, 1H), 1.64-1.86 (m, 3H); MS (ES+) m/z 502.3 (M+1), Rt=138 min.

Sources & evidence

ORD record
ord-ece41c203bb640d494792808549b530a
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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