5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 67380355, compound

HRID 1397426Notes

Reaction equation

HRID 1397426 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[O:7][CH:8]=1.[F:17][C:18]([F:34])([F:33])[C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:32]=2)[C:29](O)=[O:30])[N:20]=1>>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([C:6]2[O:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:29](=[O:30])[C:28]3[CH:32]=[C:24]([C:21]4[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=4)[CH:25]=[N:26][CH:27]=3)[N:5]=2)=[CH:10][CH:11]=1)#[N:14]

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67324352HCID 67324352, compound

Product 1

HCID 67380355HCID 67380355, compoundYield 23%

Procedure

This compound was synthesized from 4-(4-(2-aminoethyl)oxazol-2-yl)benzonitrile and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (30 mg, yield 23%) as an off white solid. 1H NMR (400 MHz, CDCl3) δ 9.69 (m, 1H), 9.47 (m, 1H), 9.18 (m, 1H), 8.18-8.16 (d, J=8.3 Hz, 2H), 7.78-7.76 (d, J=8.8 Hz, 2H), 7.71 (s, 1H), 3.92-3.91 (m, 2H), 3.05-3.02 (t, J=6.0 Hz, 2H). MS (ESI) m/z: Calculated for C21H13F3N6O3: 454.10. found: 453.2 (M−H)−.

Sources & evidence

ORD record
ord-6cfaa95b4c204937ba08f46f62099ade
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…