3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67326285, compound

HRID 1397314Notes

Reaction equation

HRID 1397314 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[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>>[CH3:1][N:2]([CH2:3][C:4]1([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)[C:31](=[O:32])[C:30]1[CH:34]=[CH:35][CH:36]=[C:28]([C:25]2[N:24]=[C:23]([C:22]([F:38])([F:37])[F:21])[O:27][N:26]=2)[CH:29]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67323666HCID 67323666, compound

Product 1

HCID 67326285HCID 67326285, compoundYield 14%

Procedure

This compound was synthesized from N-methyl-1-(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (30 mg, yield 14%). 1H NMR (400 MHz, CDCl3) δ 8.13-8.09 (m, 2H), 7.96-7.94 (m, 2H), 7.57-7.55 (m, 2H), 7.48-7.41 (m, 3H), 7.36-7.32 (m, 1H), 3.99-3.96 (m, 2H), 3.92 (s, 2H), 3.66-3.60 (m, 2H), 2.53 (s, 3H), 2.48-2.44 (m, 2H), 2.23-2.16 (m, 2H). MS (ESI) m/z: Calculated for C26H23F3N4O3S: 528.14. found: 529.2 (M+H)+.

Sources & evidence

ORD record
ord-a46d12301baf4f5a8ce65e93365c4983
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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