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

HRID 1766526Notes

Reaction equation

HRID 1766526 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.[CH:28]1([C:31]([OH:35])([CH3:34])[CH2:32][NH2:33])[CH2:30][CH2:29]1>>[CH:28]1([C@:31]([OH:35])([CH3:34])[CH2:32][NH:33][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)[CH2:30][CH2:29]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 23, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethanol (commercially available), 4-fluorophenylboronic acid (commercially available) and 2-cyclopropyl-2-hydroxy-propylamine (commercially available) as starting materials. The two enantiomers were separated by column chromatography on chiral phase. MS (m/e): 385.3 (MH+).

Workup

  1. customdescribed for the preparation of Example 23
  2. customThe two enantiomers were separated by column chromatography on chiral phase

Sources & evidence

ORD record
ord-9f9bf67f31a04374a4366e4ce5b1e69b
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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