5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 67324923, compound

HRID 1397391Notes

Reaction equation

HRID 1397391 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([CH3:10])[CH2:8][NH2:9])=[CH:5][N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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>>[CH3:1][N:2]1[C:6]([CH:7]([CH3:10])[CH2:8][NH:9][C:29](=[O:30])[C:28]2[CH:32]=[C:24]([C:21]3[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=3)[CH:25]=[N:26][CH:27]=2)=[CH:5][N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67325741HCID 67325741, compound

Product 1

HCID 67324923HCID 67324923, compoundYield 28%

Procedure

This compound was synthesized from 2-(1-methyl-2-phenyl-1H-imidazol-5-yl)propan-1-amine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (35 mg, yield 28%). 1H NMR (400 MHz, DMSO-d6) δ 9.36 (d, J=2.1 Hz, 1H), 9.28-9.26 (m, 2H), 8.84-8.83 (t, J=2.0 Hz, 1H), 7.65-7.63 (m, 2H), 7.50-7.42 (m, 4H), 6.92 (s, 1H), 3.70 (s, 3H), 3.66-3.61 (m, 1H), 3.32-3.28 (m, 1H), 3.22-3.17 (m, 1H), 1.33-1.32 (d, J=6.7 Hz, 3H). MS (ESI) m/z: Calculated for C22H19F3N6O2: 456.15. found: 457.2 (M+H)+.

Sources & evidence

ORD record
ord-11b60e989d2843b999175b9a722ef2a4
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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