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

HRID 874948Notes

Reaction equation

HRID 874948 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH2:11][CH:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=2)[CH2:9]1.[F:20][C:21]([F:37])([F:36])[C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30](O)=[O:31])[N:23]=1>>[F:36][C:21]([F:20])([F:37])[C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([N:8]2[CH2:9][CH:10]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=3)[CH2:11]2)=[O:31])[N:23]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 866735326-(azetidin-3-yl)nicotinonitrile TFA salt

Product 1

HCID 533278116-(1-(3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)azetidin-3-yl)nicotinonitrileYield 47%

Procedure

This compound was synthesized from 6-(azetidin-3-yl)nicotinonitrile TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (70 mg, yield 47%). 1H NMR (400 MHz, DMSO-d6) δ 9.06 (m, 1H), 8.30-8.29 (m, 2H), 8.21-8.19 (d, J=7.8 Hz, 1H), 7.96-7.94 (d, J=7.8 Hz, 1H), 7.74-7.70 (t, J=7.7 Hz, 1H), 7.63-7.61 (d, J=8.1 Hz, 1H), 4.76-4.72 (m, 1H), 4.52-4.46 (m, 2H), 4.25-4.18 (m, 2H). MS (ESI) m/z: Calculated for C19H12F3N5O2: 399.09. found: 400.2 (M+H)+

Sources & evidence

ORD record
ord-907124eb5b87454aa472bac6fc187946
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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