3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67346828, compound

HRID 1397225Notes

Reaction equation

HRID 1397225 reaction equation
[CH3:1][C:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)([CH3:5])[CH2:3][NH2:4].[F:17][C:18]([F:34])([F:33])[C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])[N:20]=1>>[CH3:5][C:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)([CH3:1])[CH2:3][NH:4][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([C:21]2[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324345HCID 67324345, compound

Product 1

HCID 67346828HCID 67346828, compoundYield 38%

Procedure

This compound was synthesized from 2-methyl-2-(4-phenylthiazol-2-yl)propan-1-amine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (75 mg, yield 38%). 1H NMR (400 MHz, MeOD) δ 8.52 (t, J=1.8 Hz, 1H), 8.27 (d, J=7.8 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.92-7.90 (m, 2H), 7.69 (s, 1H), 7.67-7.63 (t, J=7.8 Hz, 1H), 7.36-7.29 (m, 2H), 7.28-7.26 (m, 1H), 3.79 (d, J=6.3 Hz, 2H), 1.58 (s, 6H). MS (ESI) m/z: Calculated for C23H19F3N4O2S: 472.12. found: 473.0 (M+H)+.

Sources & evidence

ORD record
ord-aae9506f518847a68f14f8497dce317f
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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