3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67325620, compound

HRID 1397294Notes

Reaction equation

HRID 1397294 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]([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)[CH2:4][NH2:5].[F:18][C:19]([F:35])([F:34])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])[N:21]=1>>[CH3:1][N:2]([CH3:17])[CH:3]([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)[CH2:4][NH:5][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:22]2[N:21]=[C:20]([C:19]([F:35])([F:34])[F:18])[O:24][N:23]=2)[CH:26]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324466HCID 67324466, compound

Product 1

HCID 67325620HCID 67325620, compoundYield 17%

Procedure

This compound was synthesized from N,N-dimethyl-1-(4-phenylthiazol-2-yl)ethane-1,2-diamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (16 mg, yield 17%). 1H NMR (400 MHz, CDCl3) δ 8.57-8.56 (t, J=1.5 Hz, 1H), 8.26-8.23 (dt, J=7.8 Hz, 1.4 Hz, 1H), 8.07-8.05 (dt, J=7.8 Hz, 1.4 Hz, 1H), 7.91-7.87 (m, 3H), 7.63-7.59 (t, J=7.8 Hz, 1H), 7.51 (s, 1H), 7.42-7.38 (m, 2H), 7.36-7.31 (m, 1H), 4.35-4.29 (ddd, J=13.2 Hz, 6.6 Hz, 5.5 Hz, 1H), 4.15-4.12 (m, 1H), 3.85-3.78 (ddd, J=13.0 Hz, 8.3 Hz, 4.6 Hz, 1H), 2.51 (s, 6H). MS (ESI) m/z: Calculated for C23H20F3N5O2S: 487.13. found: 488.2 (M+H)+.

Sources & evidence

ORD record
ord-54e2ded3baac488992bce168f0662e9e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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