3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 53327833, compound

HRID 874960Notes

Reaction equation

HRID 874960 reaction equation
Cl.[CH3:2][C:3]1([CH3:17])[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1.[F:18][C:19]([F:35])([F:34])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])[N:21]=1>>[CH3:2][C:3]1([CH3:17])[CH2:8][N:7]([C:28](=[O:29])[C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([C:22]3[N:21]=[C:20]([C:19]([F:35])([F:34])[F:18])[O:24][N:23]=3)[CH:26]=2)[CH2:6][CH2:5][N:4]1[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324559HCID 67324559, compound

Product 1

HCID 53327833HCID 53327833, compoundYield 33%

Procedure

This compound was synthesized from 6-(2,2-dimethylpiperazin-1-yl)nicotinonitrile hydrochloride and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (50 mg, yield 33%). 1H NMR (400 MHz, MeOD) δ 8.43 (d, J=1.8 Hz, 1H), 8.29-8.22 (m, 2H), 7.75-7.72 (m, 3H), 6.88 (d, J=9.0 Hz, 1H), 4.05-3.85 (m, 4H), 3.67 (m, 2H), 1.67-1.47 (m, 6H). MS (ESI) m/z: Calculated for C22H19F3N6O2: 456.15. found: 457.2 (M+H)+

Sources & evidence

ORD record
ord-76652958c75e4afcae119dcea99abec6
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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