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

HRID 1766519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766519
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

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e8df2fe220314aea834388ec9cdd746a
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229999B2

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