3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950332, compound

HRID 1397360Notes

Reaction equation

HRID 1397360 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]3([CH2:20][NH2:21])[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[N:12]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:39])([F:38])[C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[N:25]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]3([CH2:20][NH:21][C:32](=[O:33])[C:31]4[CH:35]=[CH:36][CH:37]=[C:29]([C:26]5[N:25]=[C:24]([C:23]([F:39])([F:38])[F:22])[O:28][N:27]=5)[CH:30]=4)[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67321794HCID 67321794, compound

Product 1

HCID 69950332HCID 69950332, compoundYield 24%

Procedure

This compound was synthesized from (4-(2-(4-fluorophenyl)oxazol-4-yl)-1-methylpiperidin-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (50 mg, yield 24%). 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 8.29-8.27 (m, 1H), 8.13-8.05 (m, 3H), 7.67-7.62 (m, 2H), 7.17-7.13 (t, J=8.7 Hz, 2H), 3.85-3.84 (m, 2H), 3.14-3.00 (m, 4H), 2.67 (m, 3H), 2.43-2.42 (m, 2H), 2.24-2.23 (m, 2H). MS (ESI) m/z: Calculated for C26H23F4N5O3: 529.17. found: 530.2 (M+H)+.

Sources & evidence

ORD record
ord-5d6765fe1c364c8792e86dc4c792f28c
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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