2-(2-(4-Chlorophenyl)thiazol-4-yl)ethanamine → N-(2-(2-(4-Chlorophenyl)thiazol-4-yl)ethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

HRID 1397281Notes

Reaction equation

HRID 1397281 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([CH:31]=2)[C:28](O)=[O:29])[N:19]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH:15][C:28](=[O:29])[C:27]3[CH:31]=[C:23]([C:20]4[N:19]=[C:18]([C:17]([F:33])([F:32])[F:16])[O:22][N:21]=4)[CH:24]=[N:25][CH:26]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 226902632-(2-(4-Chlorophenyl)thiazol-4-yl)ethanamineHCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 67379423N-(2-(2-(4-Chlorophenyl)thiazol-4-yl)ethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 23%

Procedure

This compound was synthesized from 2-(2-(4-chlorophenyl)thiazol-4-yl)ethanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (13 mg, yield 23%). 1H NMR (400 MHz, CDCl3) δ 9.46 (m, 1H), 9.25 (m, 1H), 8.81-8.80 (t, J=2 Hz, 1H), 7.87-7.84 (m, 2H), 7.40-7.37 (m, 2H), 7.08 (s, 1H), 3.93-3.89 (m, 2H), 3.16-3.13 (m, 2H). MS (ESI) m/z: Calculated for C20H13ClF3N5O2S: 479.04. found: 480.0 (M+H)+.

Sources & evidence

ORD record
ord-79799d0ae25d4f5e8a344d7c0633d4fb
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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