Cyclohexanemethylamine → 1-ethyl-6-(methylsulfinyl)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375903ノート

反応式

HRID 375903 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17]([CH3:19])=[O:18])=[CH:11][CH:10]=3)[CH3:2].[CH:20]1([CH2:26][NH2:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:27][CH2:26][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17]([CH3:19])=[O:18])=[CH:11][CH:10]=3)[CH3:2]

参加物

4

反応物 2

HCID 76688CyclohexanemethylamineHCID 212176981-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline

生成物 1

HCID 212177091-ethyl-6-(methylsulfinyl)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine収率 11.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline (0.4 g, 2.8 mmol), DMSO (1.5 mL) and cyclohexylmethylamine (0.73 mL, 5.6 mmol) was heated at 110° C. over night. The reaction mixture was cooled to room temperature, then was partitioned between CHCl3 (20 mL) and water (20 mL) containing NH4OH (3 mL). The layers were separated, the aqueous layer was extracted with CH2Cl2 (10 mL) and the organic layers were combined dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate, followed by recrystallization from ethyl acetate (2×) to afford 0.115 g of 1-ethyl-6-(methylsulfinyl)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 186°-187° C.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwas partitioned between CHCl3 (20 mL) and water (20 mL)
  3. additioncontaining NH4OH (3 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (10 mL)
  6. dry with materialthe organic layers were combined dried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  9. customfollowed by recrystallization from ethyl acetate (2×)

出典と根拠

ORDレコード
ord-d36773cf84eb4c38b7859f21c5d24564
出典データセット
uspto-grants-1996_01
特許番号
US05488055

反応ノート

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