6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid → 6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (3-trifluoromethyl-[1,2,4]oxadiazol-5-ylmethyl)-amide

HRID 1026022Notes

Reaction equation

HRID 1026022 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][C:9]=2[O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:4][CH:3]=1.Cl.[F:24][C:25]([F:34])([F:33])[C:26]1[N:30]=[C:29]([CH2:31][NH2:32])[O:28][N:27]=1>>[F:34][C:25]([F:24])([F:33])[C:26]1[N:30]=[C:29]([CH2:31][NH:32][C:14]([C:12]2[CH:11]=[CH:10][C:9]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:13]=2)=[O:16])[O:28][N:27]=1

Participants

3

Reactant 2

HCID 666784836-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochloride

Product 1

HCID 569283816-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (3-trifluoromethyl-[1,2,4]oxadiazol-5-ylmethyl)-amide

Procedure

The title compound was synthesized in analogy to Example 1, using 6-(4-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example AF) and C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methylamine hydrochloride (CAS registry No. 944905-93-5; example AK) as starting materials; LC-MS (UV peak area/ESI) 100%, 479.0355 (M−H)−.

Sources & evidence

ORD record
ord-8f148eea52cf489287a807b85f6c2361
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

Loading…