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

HRID 1766519노트

반응식

HRID 1766519 반응식
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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8df2fe220314aea834388ec9cdd746a
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229999B2

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