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

HRID 1586187노트

반응식

HRID 1586187 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
110 °C

실험 절차

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) is heated at 110° C. over night. The reaction mixture is cooled to room temperature, then is partitioned between CHCl3 (20 ml) and water (20 ml) containing NH4OH (3 ml). The layers are separated, the aqueous layer is extracted with CH2Cl2 (10 ml), and the organic layers are combined dried over MgSO4 and evaporated. The residue is 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.

후처리

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

출처 및 근거

ORD 기록
ord-081daccbb8aa4eeca574ff1b16c6e607
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942520

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