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

HRID 874926Notes

Reaction equation

HRID 874926 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)[N:4]=1.Cl.[CH3:20][CH:21]1[CH2:26][NH:25][CH2:24][CH2:23][N:22]1[C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=1>>[CH3:20][CH:21]1[CH2:26][N:25]([C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([C:5]3[N:4]=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=3)[CH:9]=2)[CH2:24][CH2:23][N:22]1[C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673239496-(2-Methylpiperazin-1-yl)nicotinonitrile hydrochloride

Product 1

HCID 533277696-(2-Methyl-4-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazin-1-yl)nicotinonitrileYield 43%

Procedure

This compound was synthesized from 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid and 6-(2-methylpiperazin-1-yl)nicotinonitrile hydrochloride as described for example 37 step 3 (70 mg, yield 43%). 1H NMR (400 MHz, MeOD) δ 8.43 (d, J=2.0 Hz, 1H), 8.27 (m, 1H), 8.22 (s, 1H), 7.78-7.73 (m, 3H), 6.86 (d, J=9.0 Hz, 1H), 4.66-4.56 (m, 2H), 4.34-4.29 (m, 1H), 3.85-3.83 (m, 1H), 3.65 (m, 1H), 3.49-3.40 (m, 1H), 3.26 (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-258788814e204fc99ef5b73bdb0e2754
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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