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

HRID 874930Notes

Reaction equation

HRID 874930 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH2:3]1.[F:17][C:18]([F:34])([F:33])[C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])[N:20]=1>>[CH3:1][CH:2]1[N:7]([C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([C:21]3[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=3)[CH:25]=2)[CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 625880796-(3,5-Dimethylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 533277876-(3,5-Dimethyl-4-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazin-1-yl)nicotinonitrileYield 18%

Procedure

This compound was synthesized from 6-(3,5-dimethylpiperazin-1-yl)nicotinonitrile and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (35 mg, yield 18%). 1H NMR (400 MHz, CDCl3) δ 8.42 (d, J=1.8 Hz, 1H), 8.22 (dt, J=7.2 Hz, J=1.7 Hz, 1H), 8.16 (s, 1H), 7.68-7.62 (m, 3H), 6.66 (d, J=9.0 Hz, 1H), 4.46 (m, 2H), 4.29 (d, J=13.8 Hz, 1H), 3.36 (m, 2H), 1.16 (d, J=6.3 Hz, 6H). MS (ESI) m/z: Calculated for C22H19F3N6O2: 456.15. found: 457.2 (M+H)+.

Sources & evidence

ORD record
ord-f8146702588c46a6a3a2726cdf75d4a3
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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