(4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methanamine → N-((4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

HRID 1397278Notes

Reaction equation

HRID 1397278 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3([CH2:20][NH2:21])[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[N:12]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:39])([F:38])[C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:30]=[N:31][CH:32]=[C:33]([CH:37]=2)[C:34](O)=[O:35])[N:25]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3([CH2:20][NH:21][C:34](=[O:35])[C:33]4[CH:37]=[C:29]([C:26]5[N:25]=[C:24]([C:23]([F:39])([F:38])[F:22])[O:28][N:27]=5)[CH:30]=[N:31][CH:32]=4)[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 67323091(4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methanamineHCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 67324198N-((4-(2-(4-Chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 11%

Procedure

This compound was synthesized from (4-(2-(4-chlorophenyl)thiazol-4-yl)-1-methylpiperidin-4-yl)methanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (17 mg, yield 11%). 1H NMR (400 MHz, MeOD) δ 9.36 (d, J=2.0 Hz, 1H), 9.09 (d, J=2.0 Hz, 1H), 8.72 (t, J=2.0 Hz, 1H), 7.95-7.93 (d, J=8.5 Hz, 2H), 7.59 (br s, 1H), 7.44-7.42 (d, J=8.6 Hz, 2H), 3.73 (m, 2H), 3.50-3.49 (m, 2H), 2.87-2.83 (m, 7H), 2.21-2.16 (m, 2H). MS (ESI) m/z: Calculated for C25H22ClF3N6O2S: 562.12. found: 563.2 (M+H)+.

Sources & evidence

ORD record
ord-209c31741d25466d840442744875b6e6
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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