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

HRID 375903노트

반응식

HRID 375903 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) 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.

후처리

  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×)

출처 및 근거

ORD 기록
ord-d36773cf84eb4c38b7859f21c5d24564
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488055

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