3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69935727, compound

HRID 875039Notes

Reaction equation

HRID 875039 reaction equation
OC(C(F)(F)F)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][C@@H:18]2[CH2:20][C@H:15]1[CH2:16][NH:17]2.[F:21][C:22]([F:38])([F:37])[C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31](O)=[O:32])[N:24]=1>>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][C@@H:18]2[CH2:20][C@H:15]1[CH2:16][N:17]2[C:31]([C:30]1[CH:34]=[CH:35][CH:36]=[C:28]([C:25]2[N:24]=[C:23]([C:22]([F:37])([F:21])[F:38])[O:27][N:26]=2)[CH:29]=1)=[O:32]

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 131732580HCID 131732580, compound

Product 1

HCID 69935727HCID 69935727, compoundYield 27%

Procedure

This compound was synthesized from (1S,4S)-2-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (30 mg, yield 27%). 1H NMR (400 MHz, CDCl3) δ8.28-8.07 (m, 3H), 7.74-7.71 (m, 1H), 7.65-7.43 (m, 2H), 6.66-6.55 (m, 1H), 6.45-6.33 (m, 1H), 5.16-4.94 (m, 2H), 3.82-3.49 (m, 4H), 2.10-2.05 (m, 2H). MS (ESI) m/z: Calculated for C20H16F3N5O2: 415.13. found: 416.2 (M+H)+

Sources & evidence

ORD record
ord-a1f448eee5d240828960f4ad2f38b93d
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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