HCID 53628661, 화합물 → 4-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 1260232노트

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HRID 1260232 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([C:24](=O)[CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([CH2:24][CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

참가 물질

3

반응물 1

HCID 53628661HCID 53628661, 화합물

생성물 1

HCID 536286604-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide수율 66.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-isopropyl-N-[6-(1-propionyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide (150 mg, 0.38 mmol) in THF (15 ml) was added dropwise 1M BH3. THF (3.8 ml) and the mixture was stirred at room temperature for 12 h. It was then quenched by careful addition of 1N aqueous HCl (10 ml) and the resulting solution was heated at reflux for 4 h. The solution was next cooled to room temperature, adjusted to pH˜8 with 2 N NaOH solution and diluted with CH2Cl2. Separation of the layers, drying (Na2SO4) of the organic phase, filtration and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (CH2Cl2:methanol, 95:5) to give the title compound (95 mg, 66%) as a light yellow oil.

후처리

  1. customIt was then quenched by careful addition of 1N aqueous HCl (10 ml)
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 4 h
  4. additiondiluted with CH2Cl2
  5. customSeparation of the layers
  6. customdrying
  7. filtration(Na2SO4) of the organic phase, filtration and evaporation in vacuo
  8. customprovided the crude material, which
  9. customwas purified by flash column chromatography (CH2Cl2:methanol, 95:5)

출처 및 근거

ORD 기록
ord-f7309eb9ad3f4c8e976c1c866bf44c97
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470810B2

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