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

HRID 874928Notes

Reaction equation

HRID 874928 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[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>>[CH3:1][CH:2]1[N:7]([C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:20]3[N:19]=[C:18]([C:17]([F:33])([F:32])[F:16])[O:22][N:21]=3)[CH:24]=2)[CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 624798016-(3-Methylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 533277706-(3-Methyl-4-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazin-1-yl)nicotinonitrileYield 39%

Procedure

This compound was synthesized from 6-(3-methylpiperazin-1-yl)nicotinonitrile and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (75 mg, yield 39%). 1H NMR (400 MHz, MeOD) δ 8.41 (d, J=2.0 Hz, 1H), 8.27-8.25 (m, 1H), 8.18 (s, 1H), 7.77-7.72 (m, 3H), 6.89 (d, J=9.0 Hz, 1H), 4.39 (m, 3H), 3.48 (m, 2H), 3.22-3.15 (m, 1H), 1.29 (m, 3H). MS (ESI) m/z: Calculated for C21H17F3N6O2: 442.14. found: 443.2 (M+H)+.

Sources & evidence

ORD record
ord-3fac6b0bde38424dbd43da1e2756a960
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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