Propylamine → 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamide

HRID 2105106

반응식

HRID 2105106 반응식
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.[Na].[NH:17]1C2[C:22](=CC(S(O)(=O)=O)=CC=2)[C:20](=O)[C:18]1=O.O=P(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.C(N)CC>C1COCC1.C(OCC)(=O)C>[CH2:18]([NH:17][S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13])[CH2:20][CH3:22]

참가 물질

9

반응물 6

HCID 7852PropylamineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 817492,3-Dioxo-5-indolinesulfonic acidHCID 5360545SodiumHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

생성물 1

HCID 112771782,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamide수율 60%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonyl chloride (0.10 g, 0.41 mmol), prepared by the reaction of the sodium salt of 5-isatinsulfonic acid with POCl3, was dissolved in 5 mL THF. This solution was cooled in an ice bath and DIEA (0.14 mL, 2.0 eq) was added slowly, followed by n-propylamine (35 uL, 1.0 eq). Stirring was continued for 40 min and the solution was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by SiO2 chromatography to give the title compound (65 mg, 60%).

후처리

  1. temperatureThis solution was cooled in an ice bath
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by SiO2 chromatography

출처 및 근거

ORD 기록
ord-d7368123a74f408e92f032ad28f2ba41
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579313B2

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