Water → N-{4-[methyl-(2-pyridin-2-yl-ethyl)sulfamoyl]phenyl}acetamide

HRID 17829

반응식

HRID 17829 반응식
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)(=[O:13])[CH3:12].O>CC(C)=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[S:21]([C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:11](=[O:13])[CH3:12])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

참가 물질

5

반응물 3

HCID 962WaterHCID 2366BetahistineHCID 8481N-Acetylsulfanilyl chloride

생성물 1

HCID 52254087N-{4-[methyl-(2-pyridin-2-yl-ethyl)sulfamoyl]phenyl}acetamide수율 78.5%

시약·촉매·용매 1

HCID 180Acetone용매2회

반응 조건

온도
0 °C

실험 절차

(prepared according to an analogous procedure described in U.S. Pat. No. 5,755,873) Step A: Methyl-(2-pyridin-2-ylethyl)amine (8.9 ml, 0.0643 mol) was dissolved in acetone (13 ml) and cooled to 0° C., 4-acetylaminobenzenesulfonyl chloride (5 g, 0.0214 mol) was added over 10 min. Additional acetone (5 ml) was added and the mixture was heated at reflux for 2 h. After cooling to rt, the mixture was added to water and extracted with EtOAc. The extracts were dried (MgSO4). The mixture was concentrated under reduced pressure and purified by flash chromatography (SiO2, EtOAc-MeOH/EtOAc 1:19) to give 5.6 g of N-{4-[methyl-(2-pyridin-2-yl-ethyl)sulfamoyl]phenyl}acetamide. Step B: The compound from step A (5.6 g) was suspended in water (22.4 ml), treated with concentrated HCl (13.4 ml), and the mixture heated at reflux for 1 h. After cooling to rt, NH4OH (13.7 ml) was added with stirring. The resulting mixture was extracted with CH2Cl2; the extracts were washed with water, dried (MgSO4), and concentrated under reduced pressure to give 4.8 g of 4-amino-N-methyl-N-(2-pyridin-2-ylethyl)benzenesulfonamide. LCMS: MH+=292.0.

후처리

  1. custom(prepared
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 h
  4. temperatureAfter cooling to rt
  5. extractionextracted with EtOAc
  6. dry with materialThe extracts were dried (MgSO4)
  7. concentrationThe mixture was concentrated under reduced pressure
  8. custompurified by flash chromatography (SiO2, EtOAc-MeOH/EtOAc 1:19)

출처 및 근거

ORD 기록
ord-f82bf14d6f8749feb0a287637b8666cb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741318B2

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