(3-(Trifluoromethyl)-1,2,4-oxadiazol-5-YL)methanamine → (R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide

HRID 1026095Notes

Reaction equation

HRID 1026095 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:17][C@@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=O)=[CH:4][CH:3]=1.[F:23][C:24]([F:33])([F:32])[C:25]1[N:29]=[C:28]([CH2:30][NH2:31])[O:27][N:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:17][C@@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([NH:31][CH2:30][C:28]2[O:27][N:26]=[C:25]([C:24]([F:33])([F:32])[F:23])[N:29]=2)=[O:15])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 55263061(3-(Trifluoromethyl)-1,2,4-oxadiazol-5-YL)methanamineHCID 66678800(R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)nicotinic acid

Product 1

HCID 56929661(R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide

Procedure

The title compound was synthesized in analogy to Example 1 using (R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)nicotinic acid (example CJ) and 3-trifluoromethyl-[1,2,4]oxadiazol-5-methanamine (example AK) as starting materials; LC-MS (UV peak area/ESI) 94.6%, 469.1 (M+H)+.

Sources & evidence

ORD record
ord-80089222a80241c193edd5ed6e3aab74
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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