3-(Methylaminomethyl)pyridine → HCID 59489545, compound

HRID 1879162Notes

Reaction equation

HRID 1879162 reaction equation
FC1C=CC(CNC)=CC=1.[CH3:11][NH:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[F:20][C:21]1[CH:43]=[CH:42][C:24]([CH2:25][NH:26][C:27]([C:29]2[S:33][C:32]([C:34]3[CH:39]=[N:38][CH:37]=[C:36](I)[N:35]=3)=[N:31][C:30]=2[CH3:41])=[O:28])=[CH:23][CH:22]=1>>[F:20][C:21]1[CH:43]=[CH:42][C:24]([CH2:25][NH:26][C:27]([C:29]2[S:33][C:32]([C:34]3[CH:39]=[N:38][CH:37]=[C:36]([N:12]([CH3:11])[CH2:13][C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[N:35]=3)=[N:31][C:30]=2[CH3:41])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 883933-(Methylaminomethyl)pyridineHCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 866455582-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fluoro benzylamide

Product 1

HCID 59489545HCID 59489545, compoundYield 78%

Procedure

Following the procedure described in Example 14, making variations as required to replace 4-fluoro-N-methyl-benzylamine with methyl-pyridin-3-ylmethyl-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 78% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.58-8.65 (m, 2H), 8.45-8.49 (m, 1H), 8.11 (s, 1H), 7.62-7.68 (m, 1H), 7.29-7.37 (m, 2H), 7.22-7.28 (m, 1H), 6.98-7.08 (m, 2H), 6.35 (bs, 1H), 4.84 (s, 2H), 4.54 (d, J=8.0 Hz, 2H), 3.18 (s, 3H), 2.69 (s, 3H); MS (ES+) m/z 449.2 (M+1), Rt=1.32 min.

Sources & evidence

ORD record
ord-dde92361b0404d7994747e34180dec57
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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