3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 69950154, compound

HRID 1397235Notes

Reaction equation

HRID 1397235 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[C:9]([C:12]2([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[S:10][CH:11]=1.[F:20][C:21]([F:37])([F:36])[C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30](O)=[O:31])[N:23]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[C:9]([C:12]2([CH2:18][NH:19][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][CH:35]=[C:27]([C:24]4[N:23]=[C:22]([C:21]([F:37])([F:36])[F:20])[O:26][N:25]=4)[CH:28]=3)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[S:10][CH:11]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324504HCID 67324504, compound

Product 1

HCID 69950154HCID 69950154, compoundYield 13%

Procedure

This compound was synthesized from (4-(4-(pyridin-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 (35 mg, yield 13%). 1H NMR (400 MHz, MeOD) δ 8.54 (d, J=5.5 Hz, 1H), 8.44 (m, 1H), 8.25 (d, J=8.0 Hz, 1H), 8.17 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.97 (d, J=7.8 Hz, 1H), 7.79 (td, J=7.7 Hz, 1.6 Hz, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.32 (m, 1H), 3.97-3.93 (dt, J=11.8 Hz, 3.8 Hz, 2H), 3.75 (m, 2H), 3.62-3.56 (m, 2H), 2.47-2.44 (m, 2H), 2.12-2.08 (ddd, J=14.1 Hz, 10.5 Hz, 4.3 Hz, 2H). MS (ESI) m/z: Calculated for C24H20F3N5O3S: 515.12. found: 516.0 (M+H)+.

Sources & evidence

ORD record
ord-aff353527b0243c9830d4bb9e900f3a1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…