Thionyl Chloride → 4-tert-butyl-N-[6-{2-(5-ethylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

HRID 1082272노트

반응식

HRID 1082272 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([O:30][CH2:31][CH2:32][O:33][C:34]3[N:39]=[CH:38][C:37]([CH:40](O)[CH3:41])=[CH:36][N:35]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([O:30][CH2:31][CH2:32][O:33][C:34]3[N:35]=[CH:36][C:37]([CH2:40][CH3:41])=[CH:38][N:39]=3)[N:18]=[CH:17][N:16]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 196894724-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

생성물 1

HCID 196894794-tert-butyl-N-[6-{2-(5-ethylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide수율 93.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (150 mg) in methylene chloride (3 ml) is added thionyl chloride (90 mg), and the mixture is reacted at room temperature for 0.5 hour. The reaction solution is concentrated to dryness under reduced pressure, and to the residue are added 10% palladium-carbon (30 mg), triethylamine (76 mg) and ethanol (3 ml), and the mixture is stirred at room temperature for two hours under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated to dryness under reduced pressure. The residue is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-ethylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (137 mg) as crystals.

후처리

  1. customthe mixture is reacted at room temperature for 0.5 hour
  2. concentrationThe reaction solution is concentrated to dryness under reduced pressure
  3. additionto the residue are added 10% palladium-carbon (30 mg), triethylamine (76 mg) and ethanol (3 ml)
  4. customThe catalyst is removed by filtration
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure
  6. extractionThe residue is extracted with ethyl acetate
  7. washthe ethyl acetate layer is washed
  8. customdried
  9. customevaporated
  10. customto remove the solvent
  11. customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
  12. customrecrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-378a207a39f046c2bd26856123cec3f6
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05589478

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