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

HRID 1159269Notes

Reaction equation

HRID 1159269 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]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[NH2:28][CH2:29][C:30]([CH:33]1[CH2:35][CH2:34]1)([OH:32])[CH3:31]>>[CH:33]1([C@:30]([OH:32])([CH3:31])[CH2:29][NH:28][C:3](=[O:12])[C:4]2[CH:9]=[C:8]([C:22]3[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=3)[C:7]([O:17][CH2:16][CH:13]3[CH2:15][CH2:14]3)=[N:6][CH:5]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2856454-Fluorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 11950408N-((R)-2-Cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethanol (commercially available), 4-fluorophenylboronic acid (commercially available) and rac-1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. The two enantiomers were separated by column chromatography on chiral phase. MS (ISP): 385.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43
  2. customThe two enantiomers were separated by column chromatography on chiral phase

Sources & evidence

ORD record
ord-c2177f1206d94ec79c0eb3930416e153
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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