Nitrogen mustard hydrochloride → 8-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

HRID 271138

反応式

HRID 271138 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH:7]2.Cl.Cl[CH2:23][CH2:24][N:25]([CH2:27][CH2:28]Cl)[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)CCC>[CH3:26][N:25]1[CH2:27][CH2:28][N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][C:8]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:7]3)[CH2:23][CH2:24]1

参加物

7

反応物 5

HCID 5935Nitrogen mustard hydrochloride2 回HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 534255023-(Phenylsulfonyl)-8-quinolinamine

生成物 1

HCID 99291628-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

A solution of 8-amino-3-phenylsulfonylquinoline (D5) (38.8 g, 137 mmol) in n-butanol (360 ml) was treated with bis-(2-chloroethyl)-methyl-amine hydrochloride (40 g, 138 mmol) and sodium carbonate (72 g, 0.68 mol). The mixture was heated to a vigorous reflux (˜100° C.) for 16 h then a further portion of bis-(2-chloroethyl)-methyl-amine hydrochloride (25 g, 86 mmol) introduced and heating continued for a further 4 h. The solution was cooled and a 1:1 mixture of saturated aqueous sodium bicarbonate and aqueous 10% sodium thiosulphate solution (2 L) added. Stirring was continued at ambient temperature for 16 h then the aqueous phase was extracted with dichloromethane (3×500 ml), the combined organic phase dried over magnesium sulphate, evaporated in vacuo and subjected to chromatography on a Biotage Flash 75 apparatus (1 kg Silica gel) to afford the title compound (E1) as the free base form (11.6 g), identical spectroscopically to that prepared by the first method.

後処理

  1. temperatureThe mixture was heated to
  2. temperatureheating
  3. temperatureThe solution was cooled
  4. additionadded
  5. waitwas continued at ambient temperature for 16 h
  6. extractionthe aqueous phase was extracted with dichloromethane (3×500 ml)
  7. dry with materialthe combined organic phase dried over magnesium sulphate
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-01b565316634446383e9b2ede5e8e759
出典データセット
uspto-grants-2008_11
特許番号
US07452888B2

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