(S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acid → (S)-6-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxamide

HRID 1026035Notes

Reaction equation

HRID 1026035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[N:10][C:9]=2[O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[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:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:33][CH2:32][C:30]3[O:29][N:28]=[C:27]([C:26]([F:35])([F:34])[F:25])[N:31]=3)=[O:15])[CH:11]=[N:10][C:9]=2[O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66678820(S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acidHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochloride

Product 1

HCID 86663144(S)-6-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 1, using (S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acid (example AG) and C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methylamine hydrochloride (CAN 944905-93-5; example AK) as starting materials. MS: 494.0 (M−H)−.

Sources & evidence

ORD record
ord-c2eed7368e1c46e882846d683cc6eed3
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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