5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 53345018, compound

HRID 1397463Notes

Reaction equation

HRID 1397463 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]([CH3:16])[CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=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>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]([CH3:16])[CH2:14][NH:15][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:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67325162HCID 67325162, compound

Product 1

HCID 53345018HCID 53345018, compoundYield 28%

Procedure

This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-4-yl)propan-1-amine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (75 mg, yield 28%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 9.47-9.46 (d, J=2.0 Hz, 1H), 9.33 (d, J=2.0 Hz, 1H), 8.88-8.87 (t, J=2.1 Hz, 1H), 8.11-8.04 (m, 3H), 7.54 (d, J=1.0 Hz, 1H), 7.18-7.14 (t, J=8.8 Hz, 2H), 4.02-3.96 (ddd, J=13.2 Hz, 6.5 Hz, 4.1 Hz, 1H), 3.53-3.46 (ddd, J=13.1 Hz, 9.0 Hz, 4.3 Hz, 1H), 3.20-3.11 (m, 1H), 1.42-1.40 (d, J=7.0 Hz, 3H). MS (ESI) m/z: Calculated for C21H15F4N5O3: 461.11. found: 462.1 (M+H)+.

Sources & evidence

ORD record
ord-9e1520945f29452e9da7a0a12f616c57
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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