3,5-Dimethylpyridin-2-amine → {1-[4-(6,8-Dimethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 872304노트

반응식

HRID 872304 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH:19](Br)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][C:30]1[C:31]([NH2:37])=[N:32][CH:33]=[C:34]([CH3:36])[CH:35]=1>C(O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:37]=[C:31]4[C:30]([CH3:29])=[CH:35][C:34]([CH3:36])=[CH:33][N:32]4[C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 30163103,5-Dimethylpyridin-2-amineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

생성물 1

HCID 66665950{1-[4-(6,8-Dimethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester수율 14.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

500 mg (1.13 mmol) {1-[4-(2-Bromo-2-phenyl-acetyl)phenyl]-cyclobutyl}-carbamic acid tert.-butyl ester, 137.5 mg (1.13 mmol) 3,5-dimethyl-pyridin-2-yl-amine and molecular sieves (4 Å, dried over night at 120° C. in a drying oven) were heated in 10 mL ethanol in a Dean-Stark apparatus for 23 hours. The reaction mixture had been sucked off via a glass fibre filter and evaporated to dryness. The residue was redissolved in dichloromethane, washed with an 1 M hydrochloric acid, saturated sodium bicarbonate and brine and dried (sodium sulfate). After filtration and removal of the solvent the residue was purified by chromatography on silicagel (eluents: hexane/ethyl acetate) yielding 142.6 mg (25.8%) of the pure title compound and 77.5 mg (14.7%) of the title compound which was slightly contaminated.

후처리

  1. filtrationfilter
  2. customevaporated to dryness
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with an 1 M hydrochloric acid, saturated sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationAfter filtration and removal of the solvent the residue
  7. customwas purified by chromatography on silicagel (eluents: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-e4b2a8efa28c4287b51bc26e59eccbbb
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975265B2

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