5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → N-((1-Methyl-4-(2-phenylthiazol-4-yl)piperidin-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

HRID 1397273Notes

Reaction equation

HRID 1397273 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:19][NH2:20])([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:11][CH:12]=2)[CH2:4][CH2:3]1.[F:21][C:22]([F:38])([F:37])[C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=2)[C:33](O)=[O:34])[N:24]=1>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([CH2:19][NH:20][C:33](=[O:34])[C:32]2[CH:36]=[C:28]([C:25]3[N:24]=[C:23]([C:22]([F:38])([F:37])[F:21])[O:27][N:26]=3)[CH:29]=[N:30][CH:31]=2)([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:11][CH:12]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67325392(1-Methyl-4-(2-phenylthiazol-4-yl)piperidin-4-yl)methanamine

Product 1

HCID 69950102N-((1-Methyl-4-(2-phenylthiazol-4-yl)piperidin-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 8%

Procedure

This compound was synthesized from (1-methyl-4-(2-phenylthiazol-4-yl)piperidin-4-yl)methanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (15 mg, yield 8%). 1H NMR (400 MHz, CDCl3) δ 9.43 (d, J=1.5 Hz, 1H), 9.22 (d, J=1.8 Hz, 1H), 8.76 (m, 1H), 7.92-7.90 (m, 3H), 7.42-7.41 (m, 3H), 7.19 (s, 1H), 3.92-3.87 (m, 2H), 3.00 (m, 2H), 2.84 (m, 2H), 2.57 (m, 5H), 2.25 (m, 2H). MS (ESI) m/z: Calculated for C25H23F3N6O2S: 528.55. found: 529.2 (M+H)+.

Sources & evidence

ORD record
ord-018d16b8968041169bb42f916ea6567a
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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