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

HRID 1397310Notes

Reaction equation

HRID 1397310 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][NH2:15])[S:11][CH: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[N:9]=[C:10]([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)[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 14977692-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]ethanamineHCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 67379115N-(2-(4-(4-Chlorophenyl)thiazol-2-yl)ethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 35%

Procedure

This compound was synthesized from 2-(4-(4-chlorophenyl)thiazol-2-yl)ethanamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (65 mg, yield 35%). 1H NMR (400 MHz, CDCl3) δ 9.46 (d, J=1.8 Hz, 1H), 9.24 (d, J=1.8 Hz, 1H), 8.80 (t, J=2.1 Hz, 1H), 7.82-7.80 (m, 3H), 7.41 (s, 1H), 7.38-7.36 (m, 2H), 4.05-4.01 (q, J=5.8 Hz, 2H), 3.43-3.40 (t, J=5.9 Hz, 2H). MS (ESI) m/z: Calculated for C20H13ClF3N5O2S: 479.04. found: 480.0 (M+H)+.

Sources & evidence

ORD record
ord-17055dc0c05743a8bdccc835db9735f7
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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