5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 69950455, compound

HRID 1397408Notes

Reaction equation

HRID 1397408 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]([CH2:19][NH2:20])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[N:12]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:38])([F:37])[C:23]1[O:27][N:26]=[C:25]([C:28]2[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=2)[C:33](O)=[O:34])[N:24]=1>>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:9][CH:10]=1)[CH2:19][NH:20][C:33](=[O:34])[C:32]1[CH:36]=[C:28]([C:25]2[N:24]=[C:23]([C:22]([F:38])([F:37])[F:21])[O:27][N:26]=2)[CH:29]=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 69949973HCID 69949973, compound

Product 1

HCID 69950455HCID 69950455, compoundYield 10%

Procedure

This compound was synthesized from 3-(2-(4-fluorophenyl)oxazol-4-yl)-N1,N1-dimethylbutane-1,4-diamine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (16 mg, yield 10%). 1H NMR (400 MHz, MeOD) δ 9.39-9.38 (d, J=2.0 Hz, 1H), 9.16 (d, J=2.0 Hz, 1H), 8.85-8.84 (t, J=2.1 Hz, 1H), 8.08-8.05 (m, 2H), 7.84 (s, 1H), 7.26-7.22 (t, J=8.9 Hz, 2H), 3.79-3.66 (m, 2H), 3.18-3.11 (m, 1H), 2.63-2.46 (m, 2H), 2.37 (m, 6H), 2.06-2.00 (m, 2H). MS (ESI) m/z: Calculated for C24H22F4N6O3: 518.17. found: 519.2 (M+H)+.

Sources & evidence

ORD record
ord-2bbc1c34c34c4392a36a2612b4608a88
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…