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)methyl)nicotinonitrile

HRID 874940Notes

Reaction equation

HRID 874940 reaction equation
OC(C(F)(F)F)=O.[CH3:8][CH:9]1[NH:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)[CH2:10]1.[F:24][C:25]([F:41])([F:40])[C:26]1[O:30][N:29]=[C:28]([C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34](O)=[O:35])[N:27]=1>>[CH3:8][CH:9]1[N:14]([C:34](=[O:35])[C:33]2[CH:37]=[CH:38][CH:39]=[C:31]([C:28]3[N:27]=[C:26]([C:25]([F:41])([F:40])[F:24])[O:30][N:29]=3)[CH:32]=2)[CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)[CH2:10]1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 866735316-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt

Product 1

HCID 533278086-((3-Methyl-4-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazin-1-yl)methyl)nicotinonitrileYield 21%

Procedure

This compound was synthesized from 6-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (60 mg, yield 21%) pale yellow viscous liquid. 1H NMR (400 MHz, MeOD) δ 8.85-8.84 (m, 1H), 8.25-8.22 (dt, J=7.4 Hz, 1.6 Hz, 1H), 8.19-8.16 (dd, J=8.2 Hz, 2.1 Hz, 1H), 8.13 (m, 1H), 7.82-7.80 (d, J=8.3 Hz, 1H), 7.72-7.66 (m, 2H), 3.82-3.70 (m, 3H), 3.50 (m, 2H), 2.89 (m, 1H), 2.74 (m, 1H), 2.43-2.41 (m, 1H), 2.31-2.25 (m, 1H), 1.46-1.44 (d, J=6.5 Hz, 3H). MS (ESI) m/z: Calculated for C22H16F3N6O2: 456.15. found: 457.2 (M+H)+

Sources & evidence

ORD record
ord-1cd87e6d63b04a4fbfd81f8caa3ed45b
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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