Cyclopropanemethanol → N-((S)-2-Cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1766519Notes

Reaction equation

HRID 1766519 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[CH:31]1([C:34]([OH:38])([CH3:37])[CH2:35][NH2:36])[CH2:33][CH2:32]1>>[CH:31]1([C@@:34]([OH:38])([CH3:37])[CH2:35][NH:36][C:3](=[O:12])[C:4]2[CH:9]=[C:8]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)[C:7]([O:17][CH2:16][CH:13]3[CH2:15][CH2:14]3)=[N:6][CH:5]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 11950064N-((S)-2-Cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The two title compounds were synthesized in analogy to the procedure described for the preparation of Example 23, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethanol (commercially available), 4-trifluoromethylphenylboronic acid (commercially available) and 2-cyclopropyl-2-hydroxy-propylamine (commercially available) as starting materials and separated into the two enantiomers by column chromatography on chiral phase.

Workup

  1. customThe two title compounds were synthesized in analogy to the procedure
  2. customdescribed for the preparation of Example 23
  3. customseparated into the two enantiomers by column chromatography on chiral phase

Sources & evidence

ORD record
ord-e8df2fe220314aea834388ec9cdd746a
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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