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

HRID 1026097Notes

Reaction equation

HRID 1026097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:17][CH2:18][CH:19]3[CH2:23][CH2:22][O:21][CH2:20]3)=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13](O)=[O:14])=[CH:4][CH:3]=1.[F:24][C:25]([F:34])([F:33])[C:26]1[N:30]=[C:29]([CH2:31][NH2:32])[O:28][N:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:17][CH2:18][CH:19]3[CH2:23][CH2:22][O:21][CH2:20]3)=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([NH:32][CH2:31][C:29]2[O:28][N:27]=[C:26]([C:25]([F:34])([F:33])[F:24])[N:30]=2)=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 55263061(3-(Trifluoromethyl)-1,2,4-oxadiazol-5-YL)methanamineHCID 666784905-(4-Chloro-phenyl)-6-(tetrahydro-furan-3-ylmethoxy)-nicotinic acid

Product 1

HCID 66687152(SR)-5-(4-chlorophenyl)-6-((tetrahydrofuran-3-yl)methoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide

Procedure

The title compound was synthesized in analogy to Example 1 using 5-(4-chloro-phenyl)-6-(tetrahydro-furan-3-ylmethoxy)-nicotinic acid (example CK) and 3-trifluoromethyl-[1,2,4]oxadiazol-5-methanamine (example AK) as starting materials; enantiomers were separated by chiral HPLC (ChiralPak AD, 30% ethanol/n-heptane (+) enantiomer isolated; LC-MS (UV peak area/ESI) 100%, 483.1038 (M+H)+.

Workup

  1. customenantiomers were separated by chiral HPLC (ChiralPak AD, 30% ethanol/n-heptane (+)
  2. customenantiomer isolated

Sources & evidence

ORD record
ord-1233456b5eee4aa7a2a607a24f2d602a
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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