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

HRID 17829

反応式

HRID 17829 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 2366BetahistineHCID 8481N-Acetylsulfanilyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-f82bf14d6f8749feb0a287637b8666cb
出典データセット
uspto-grants-2010_06
特許番号
US07741318B2

関連ノート

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