3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67324627, compound

HRID 874965Notes

Reaction equation

OC(C(F)(F)F)=O.[C:8]([C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH:17]2[C:22]([O:24][CH3:25])=[O:23])=[N:14][CH:15]=1)#[N:9].[F:26][C:27]([F:43])([F:42])[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=2)[C:36](O)=[O:37])[N:29]=1>>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:36](=[O:37])[C:35]3[CH:39]=[CH:40][CH:41]=[C:33]([C:30]4[N:29]=[C:28]([C:27]([F:43])([F:42])[F:26])[O:32][N:31]=4)[CH:34]=3)[CH2:18][CH:17]2[C:22]([O:24][CH3:25])=[O:23])=[N:14][CH:15]=1)#[N:9]

Participants

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

HCID 131732579HCID 131732579, compound

Product 1

HCID 67324627HCID 67324627, compoundYield 82%

Procedure

This compound was synthesized from methyl 1-(5-cyanopyridin-2-yl)piperazine-2-carboxylate TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (80 mg, yield 82%). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=1.0 Hz, 1H), 8.26-8.23 (m, 1H), 8.18 (s, 1H), 7.76-7.73 (dd, J=8.9 Hz, 2.1 Hz, 1H), 7.65-7.64 (m, 2H), 6.73-6.71 (m, 1H), 5.43 (m, 1H), 4.68 (m, 1H), 3.94-3.90 (m, 2H), 3.73-3.68 (m, 3H), 3.59 (m, 2H), 3.28 (m, 1H). MS (ESI) m/z: Calculated for C22H17F3N6O4: 486.13. found: 487.2 (M+H)+

Sources & evidence

ORD record: ord-52f647a09b58445aadba1263176777fa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981084B2

Reaction notes

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