5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid → HCID 71212765, compound

HRID 1397451Notes

Reaction equation

HRID 1397451 reaction equation
[CH3:1][C:2]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:9][CH:10]=1)([CH3:5])[CH2:3][NH2:4].[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>>[CH3:5][C:2]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:9][CH:10]=1)([CH3:1])[CH2:3][NH:4][C:29](=[O:30])[C:28]1[CH:32]=[C:24]([C:21]2[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=2)[CH:25]=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 67325368HCID 67325368, compound

Product 1

HCID 71212765HCID 71212765, compoundYield 13%

Procedure

This compound was synthesized from 2-methyl-2-(2-phenyloxazol-4-yl)propan-1-amine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (19 mgs, 13% yield). 1H NMR (CDCl3) δ 9.45 (t, J=9.0 Hz, 1H), 9.35 (s, 1H), 8.42 (s, 1H), 8.03 (s, 2H), 7.51-7.40 (m, 4H), 3.62 (bs, 2H), 1.42 (s, 6H). MS (ESI) m/z: Calculated for C22H18F3N5O3: 457.14. found: 458.1 (M+H)+.

Sources & evidence

ORD record
ord-580b192b63ad47639f8db13575cad077
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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