3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69949904, compound

HRID 1397218Notes

Reaction equation

HRID 1397218 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:17][NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:36])([F:35])[C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](O)=[O:30])[N:22]=1>>[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:17][NH:18][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][CH:34]=[C:26]([C:23]5[N:22]=[C:21]([C:20]([F:36])([F:35])[F:19])[O:25][N:24]=5)[CH:27]=4)[CH2:16][CH2:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67325828HCID 67325828, compound

Product 1

HCID 69949904HCID 69949904, compoundYield 34%

Procedure

This compound was synthesized from (1-(4-phenylthiazol-2-yl)cyclopentyl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (65 mg, yield 34%). 1H NMR (400 MHz, DMSO-d6) 8.78 (m, 1H), 8.44 (s, 1H), 8.19 (d, J=7.6 Hz, 1H), 8.06 (d, J=7.9 Hz, 1H), 7.98 (s, 1H), 7.93 (d, J=7.3 Hz, 2H), 7.71 (t, J=7.9 Hz, 1H), 7.39 (m, 2H), 7.30 (m, 1H), 3.69 (d, J=6.2 Hz, 2H), 2.19 (m, 2H), 2.07 (m, 2H), 1.76 (m, 2H), 1.64 (m, 2H). MS (ESI) m/z: Calculated for C25H21F3N4O2S: 498.13. found: 499.2 (M+H)+.

Sources & evidence

ORD record
ord-08b145c6ac8f4a86b6bb47508b8f9b3e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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