(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid → (S)-5-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinamide

HRID 1528441Notes

Reaction equation

HRID 1528441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=O)=[CH:4][CH:3]=1.Cl.[F:25][C:26]([F:35])([F:34])[C:27]1[N:31]=[C:30]([CH2:32][NH2:33])[O:29][N:28]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:17][C@@H:18]([CH3:23])[C:19]([F:20])([F:22])[F:21])=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([NH:33][CH2:32][C:30]2[O:29][N:28]=[C:27]([C:26]([F:35])([F:34])[F:25])[N:31]=2)=[O:15])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 66678484(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acidHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochloride

Product 1

HCID 86663145(S)-5-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinamide

Procedure

The title compound was synthesized in analogy to Example 1, using (S)-5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid (Example AO) and C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methylamine hydrochloride (CAS registry No. 944905-93-5; example AK) as starting materials; MS: 493.1 (M−H)−.

Sources & evidence

ORD record
ord-4561835cf1444128beaf796eb0ef7c0d
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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