Ammonium Acetate → 1-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridin-3-yl]-2-methylpropane-1,2-diol

HRID 1882014노트

반응식

HRID 1882014 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:14](=O)[CH2:15][CH:16]([CH3:31])[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([OH:30])[C:26]([OH:29])([CH3:28])[CH3:27])=[CH:21][N:20]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:44]>C(O)(=O)C.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:44][C:17]([C:19]4[N:20]=[CH:21][C:22]([CH:25]([OH:30])[C:26]([CH3:27])([OH:29])[CH3:28])=[CH:23][CH:24]=4)=[C:16]([CH3:31])[CH:15]=3)[CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 517165Ammonium AcetateHCID 593314295-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

생성물 1

HCID 593316081-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridin-3-yl]-2-methylpropane-1,2-diol수율 66.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (235 mg) in acetic acid (5 mL) was added ammonium acetate (519 mg), and the mixture was stirred at 90° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (150 mg, yield 66%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. MS: 539 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f0fb6e860efd480fba805a4924d6eda1
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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