Dimethyl Sulfoxide → 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375877노트

반응식

HRID 375877 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][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2].CS(C)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.O>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:31][CH2:30][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 76688CyclohexanemethylamineHCID 212177041-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 212177061-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline (0.9 g, 3.3 mmol), DMSO (9 ml) and cyclohexanemethyl amine (0.86 ml, 6.6 mmol) was heated at 120°-130° C. for 6 hours. The reaction mixture was poured into water, acidified with acetic acid and the solid which formed was collected by filtration, dissolved in 5% NaOH and extracted with CH2Cl2 (2×50 ml). The aqueous layer was acidified with acetic acid and the solid which formed was collected by filtration and washed with water. The solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2 to afford 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid.

후처리

  1. temperaturewas heated at 120°-130° C. for 6 hours
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in 5% NaOH
  5. extractionextracted with CH2Cl2 (2×50 ml)
  6. customthe solid which formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customThe solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2

출처 및 근거

ORD 기록
ord-bfa05063c31b45bb80a1fa67617994d7
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488055

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