3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)aniline → 1-(4-Phenylthiazol-2-yl)-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pyrrolidine-3-carboxamide

HRID 874946Notes

Reaction equation

HRID 874946 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[N:4]=1.[C:17]1([C:23]2[N:24]=[C:25]([N:28]3[CH2:32][CH2:31][CH:30]([C:33](O)=[O:34])[CH2:29]3)[S:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:17]1([C:23]2[N:24]=[C:25]([N:28]3[CH2:32][CH2:31][CH:30]([C:33]([NH:11][C:10]4[CH:12]=[CH:13][CH:14]=[C:8]([C:5]5[N:4]=[C:3]([C:2]([F:15])([F:1])[F:16])[O:7][N:6]=5)[CH:9]=4)=[O:34])[CH2:29]3)[S:26][CH:27]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 202975493-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)anilineHCID 630313291-(4-Phenylthiazol-2-yl)pyrrolidine-3-carboxylic acid

Product 1

HCID 533278101-(4-Phenylthiazol-2-yl)-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pyrrolidine-3-carboxamideYield 28%

Procedure

This compound was synthesized from 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)aniline and 1-(4-phenylthiazol-2-yl)pyrrolidine-3-carboxylic acid as described for example 37 step 3 (20 mg, yield 28%). 1H NMR (400 MHz, MeOD) δ 8.47 (t, J=1.8 Hz, 1H), 7.88-7.81 (m, 3H), 7.57-7.53 (t, J=7.9 Hz, 1H), 7.39-7.35 (m, 2H), 7.30-7.25 (m, 2H), 6.90 (s, 1H), 3.90-3.86 (m, 1H), 3.82-3.78 (m, 1H), 3.76-3.71 (m, 1H), 3.64-3.58 (m, 1H), 3.47-3.39 (m, 1H), 2.46-2.40 (m, 2H). MS (ESI) m/z: Calculated for C23H18F3N5O2S: 485.11. found: 486.0 (M+H)+

Sources & evidence

ORD record
ord-03433d47371b4226872a629676bf4164
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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