Sodium Bicarbonate → 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine

HRID 1882122노트

반응식

HRID 1882122 반응식
[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][N:23]=1)([CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:3](=O)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O.C([O-])(=O)C.[NH4+:34].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][N:23]=1)([C:3]1[NH:34][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][CH:4]=1)[CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 593314515-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

생성물 1

HCID 593312412-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine수율 145.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To a solution of 5-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (60.7 mg) in acetic acid (1 mL) was added ammonium acetate (181 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (84.0 mg, yield 82%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9df2e48b43b74192ab914f12c22df32a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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