Sodium hydride → 1-[1-(2,3-Dihydro-1-benzofuran-5-ylsulfonyl)-5-phenyl-1H-pyrrol-3-yl]-N-methylmethanamine

HRID 554403노트

반응식

HRID 554403 반응식
C[N:2]([CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13][CH:12]=1)[C:3](=O)OC(C)(C)C.[H-].[Na+].[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:32][C:27]=2[CH2:26][CH2:25]1>CN(C)C=O>[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([S:33]([N:13]3[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:15][C:11]([CH2:10][NH:2][CH3:3])=[CH:12]3)(=[O:35])=[O:34])=[CH:32][C:27]=2[CH2:26][CH2:25]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideHCID 57522146Tert-butyl methyl[(5-phenyl-1H-pyrrol-3-YL)methyl]carbamate

생성물 1

HCID 669252451-[1-(2,3-Dihydro-1-benzofuran-5-ylsulfonyl)-5-phenyl-1H-pyrrol-3-yl]-N-methylmethanamine수율 72.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution (5 mL) of tert-butyl methyl[(5-phenyl-1H-pyrrol-3-yl)methyl]carbamate (28 mg) in N,N-dimethylformamide was added sodium hydride (60% in oil, 40 mg) at room temperature and the mixture was stirred for 30 min. 2,3-Dihydro-1-benzofuran-5-sulfonyl chloride (65 mg) was added at room temperature and the mixture was stirred for 1 hr. To the reaction mixture was added ice water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1), and dissolved in methanol (10 mL). 4 mol/l Hydrogen chloride-ethyl acetate solution (1.5 mL) was added and the mixture was stirred at 65° C. for 30 min. The reaction mixture was concentrated under reduced pressure to give a free form, which was crystallized from ethyl acetate as a 0.5 oxalic acid salt to give the title compound as pale-red crystals (yield 26 mg, 63%).

후처리

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)
  7. dissolutiondissolved in methanol (10 mL)
  8. addition4 mol/l Hydrogen chloride-ethyl acetate solution (1.5 mL) was added
  9. stirringthe mixture was stirred at 65° C. for 30 min
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. customto give a free form, which
  12. customwas crystallized from ethyl acetate as a 0.5 oxalic acid salt

출처 및 근거

ORD 기록
ord-4c7e3de235604bd395aada71fa135c21
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048909B2

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