3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → 6-(1-(3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperidin-4-yl)nicotinonitrile

HRID 874951Notes

Reaction equation

HRID 874951 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[F:32][C:17]([F:16])([F:33])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([N:2]2[CH2:3][CH2:4][CH:5]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=3)[CH2:6][CH2:7]2)=[O:27])[N:19]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673246076-(Piperidin-4-yl)nicotinonitrile hydrochloride

Product 1

HCID 533278126-(1-(3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperidin-4-yl)nicotinonitrileYield 30%

Procedure

This compound was synthesized from 6-(piperidin-4-yl)nicotinonitrile hydrochloride and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (50 mg, yield 30%). 1H NMR (400 MHz, CDCl3) δ 8.84 (d, J=2.0 Hz, 1H), 8.20-8.19 (m, 2H), 7.95-7.92 (dd, J=8.2 Hz, 2.1 Hz, 1H), 7.67-7.59 (m, 2H), 7.33 (d, J=8.3 Hz, 1H), 4.92 (m, 1H), 3.91 (m, 1H), 3.24 (m, 1H), 3.09 (m, 1H), 2.97 (m, 1H), 2.09 (m, 1H), 1.94-1.83 (m, 3H). MS (ESI) m/z: Calculated for C21H16F3N6O2: 427.13. found: 428.2 (M+H)+

Sources & evidence

ORD record
ord-4f21af5f40834d3984ec788adba98709
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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