Hydrogen chloride-ethyl acetate → 1-{5-(2-fluoropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine

HRID 2197062노트

반응식

HRID 2197062 반응식
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[N:12]([S:22]([C:25]2[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:11]=1)C)(C)(C)C.C(OCC)(=O)C.Cl>C(O)C>[F:21][C:16]1[C:15]([C:13]2[N:12]([S:22]([C:25]3[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:23])=[O:24])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

참가 물질

4

반응물 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66974551tert-butyl ({5-(2-fluoropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate

생성물 1

HCID 250026371-{5-(2-fluoropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of tert-butyl({5-(2-fluoropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (86 mg) in ethanol (2 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) at room temperature. The mixture was stirred for 2 hr, and concentrated under reduced pressure. The residue was basified with a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a free salt of the title compound as a pale-yellow oil. The obtained free salt was dissolved in ethyl acetate (2 mL) and added to a solution (2 mL) of fumaric acid (11.3 mg) in ethanol, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as colorless crystals (yield 14 mg, 18%).

후처리

  1. concentrationconcentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-572c405f0cfc4a3895f32eda0c02f9d2
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338461B2

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