4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)butanoic acid → 6((3-Methyl-4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)butanoyl)piperazin-1-yl)methyl)nicotinonitrile

HRID 874941Notes

Reaction equation

HRID 874941 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:38])([F:37])[C:26]1[O:30][N:29]=[C:28]([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[N:27]=1>>[CH3:8][CH:9]1[N:14]([C:34](=[O:35])[CH2:33][CH2:32][CH2:31][C:28]2[N:27]=[C:26]([C:25]([F:37])([F:38])[F:24])[O:30][N:29]=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 673228604-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)butanoic acidHCID 866735316-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt

Product 1

HCID 533278096((3-Methyl-4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)butanoyl)piperazin-1-yl)methyl)nicotinonitrileYield 16%

Procedure

This compound was synthesized from 6-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt and 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)butanoic acid as described for example 37 step 3 (16 mg, yield 16%) pale yellow viscous liquid. 1H NMR (400 MHz, MeOD) δ 8.82-8.81 (dd, J=2.0 Hz, 0.8 Hz, 1H), 8.15-8.12 (dd, J=8.2 Hz, 2.1 Hz, 1H), 7.77-7.75 (d, J=8.0 Hz, 1H), 3.78-3.66 (m, 2H), 2.96-2.92 (t, J=7.4 Hz, 2H), 2.89-2.85 (m, 1H), 2.73-2.69 (dt, J=11.5 Hz, 1.7 Hz, 1H), 2.51 (m, 2H), 2.34-2.30 (m, 1H), 2.22-2.17 (m, 1H), 2.14-2.06 (m, 2H), 1.35-1.32 (m, 3H), 1.30 (s, 3H). MS (ESI) m/z: Calculated for C19H21F3N6O2: 422.17. found: 423.2 (M+H)+

Sources & evidence

ORD record
ord-441f9d27d8b2418bacf213d2489e110f
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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