Dimethyl Sulfoxide → 1-ethyl-N-[[4-(methylthiomethoxycarbonyl)cyclohexyl]methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:3]=12.[NH2:17][CH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]1.[CH3:28][S:29]([CH3:31])=O>>[CH2:15]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:17][CH2:18][CH:19]4[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][S:29][CH3:31])=[O:26])[CH2:23][CH2:24]4)=[C:3]2[CH:14]=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH3:16]Participants
4
Conditions
- Temperature
- 180 °C
Procedure
A mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (3 g), DMSO (9 ml) and trans-4-(aminomethyl)cyclohexane carboxylic acid (4.1 g) was heated at 180° C. overnight. The reaction mixture was then partitioned between CH2Cl2 and water, the layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were combined, washed with water, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silca gel to afford an oil which was crystallized from ether/hexane and then recrystallized from ether/hexane to afford 1-ethyl-N-[[4-(methylthiomethoxycarbonyl) cyclohexyl]methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 135°-136° C.
Workup
- customThe reaction mixture was then partitioned between CH2Cl2 and water
- customthe layers were separated
- extractionthe aqueous layer was extracted with CH2Cl2
- washwashed with water
- dry with materialdried over Na2SO4
- customevaporated
- customThe residue was purified by column chromatography on silca gel
- customto afford an oil which
- customwas crystallized from ether/hexane
- customrecrystallized from ether/hexane
Sources & evidence
- ORD record
- ord-b91da9fbc55d42aa85ba9406b896131b
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488055
Reaction notes
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