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

HRID 874956Notes

Reaction equation

HRID 874956 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]([C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:29][CH2:28][CH:27]([C:30](O)=[O:31])[CH2:26]2)=[N:23][CH:24]=1)#[N:18]>>[C:17]([C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:29][CH2:28][CH:27]([C:30]([NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:8]([C:5]4[N:4]=[C:3]([C:2]([F:15])([F:1])[F:16])[O:7][N:6]=4)[CH:9]=3)=[O:31])[CH2:26]2)=[N:23][CH:24]=1)#[N:18]

Participants

3

Reactant 2

HCID 202975493-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)anilineHCID 630315031-(5-Cyanopyridin-2-yl)pyrrolidine-3-carboxylic acid

Product 1

HCID 533278311-(5-Cyanopyridin-2-yl)-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pyrrolidine-3-carboxamideYield 58%

Procedure

This compound was synthesized from 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)aniline and 1-(5-cyanopyridin-2-yl)pyrrolidine-3-carboxylic acid as described for example 37 step 3 (65 mg, yield 58%). 1H NMR (400 MHz, DMSO-d6) δ 10.46 (s, 1H), 8.48-8.47 (m, 2H), 7.85-7.81 (m, 2H), 7.75 (d, J=7.8 Hz, 1H), 7.58-7.54 (m, 1H), 6.59 (d, J=8.9 Hz, 1H), 3.77-3.66 (m, 3H), 3.52 (m, 1H), 3.33 (m, 1H), 2.35-2.29 (m, 1H), 2.23 (m, 1H). MS (ESI) m/z: Calculated for C20H15F3N6O2: 428.12. found: 429.0 (M+H)+

Sources & evidence

ORD record
ord-52791932ef8847019766a43ebb3269ba
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…