3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69949947, compound

HRID 1397242Notes

Reaction equation

HRID 1397242 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([C:11]2([CH2:17][NH2:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[S:9][CH:10]=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>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([C:11]2([CH2:17][NH:18][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([C:23]4[N:22]=[C:21]([C:20]([F:36])([F:35])[F:19])[O:25][N:24]=4)[CH:27]=3)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[S:9][CH:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324419HCID 67324419, compound

Product 1

HCID 69949947HCID 69949947, compoundYield 46%

Procedure

This compound was synthesized from (4-(4-(thiophen-2-yl)thiazol-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 (70 mg, yield 46%): 1H NMR (400 MHz, MeOD) δ 8.47 (t, J=1.5 Hz, 1H), 8.26 (m, 1H), 8.00 (dt, J=7.8 Hz, 1.4 Hz, 1H), 7.63-7.61 (m, 2H), 7.46 (dd, J=3.8 Hz, 1.0 Hz, 1H), 7.29 (dd, J=5.0 Hz, 1.0 Hz, 1H), 7.01 (dd, J=5.0 Hz, 3.8 Hz, 1H), 3.95-3.92 (dt, J=11.9 Hz, 4.0 Hz, 2H), 3.71 (s, 2H), 3.62-3.56 (m, 2H), 2.42-2.38 (d, J=13.8 Hz, 2H), 2.08-2.02 (ddd, J=14.3 Hz, 10.4 Hz, 4.4 Hz, 2H), MS (ESI) m/z: Calculated for C23H19F3N4O3S2: 520.09. found: 521.0 (M+H)+.

Sources & evidence

ORD record
ord-287f23b94c9249708f7dcd505153f722
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…