3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67325402, compound

HRID 1397231Notes

Reaction equation

HRID 1397231 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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][C:2]1[S:6][C:5]([C:7]2([CH2:13][NH:14][C:31](=[O:32])[C:30]3[CH:34]=[CH:35][CH:36]=[C:28]([C:25]4[N:24]=[C:23]([C:22]([F:38])([F:37])[F:21])[O:27][N:26]=4)[CH:29]=3)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324656HCID 67324656, compound

Product 1

HCID 67325402HCID 67325402, compoundYield 89%

Procedure

This compound was synthesized from (4-(5-methyl-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 (55 mg, 89% yield): 1H NMR (300 MHz, CDCl3) δ 8.48 (t, J=1.1 Hz, 1H), 8.23 (dt, J=6.2 Hz, 1.1, 1H), 7.98 (dt, J=7.9 Hz, 1.1 Hz, 1H), 7.74 (bs, 1H), 7.64 (m, 2H), 7.49 (t, J=7.7 Hz, 1H), 7.39-7.29 (m, 2H), 3.92 (m, 2H), 3.85 (d, J=5.7 Hz, 2H), 3.74 (m, 2H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H). MS (ESI) m/z: Calculated for C26H23F3N4O3S: 528.14. found: 529.1 (M+H)+.

Sources & evidence

ORD record
ord-65c891fdbd694bd5ac499bd8a81ee6ca
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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