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) is heated at 180° C. overnight. The reaction mixture is then partitioned between CH2Cl2 and water, the layers are separated and the aqueous layer is extracted with CH2Cl2. The organic layers are combined, washed with water, dried over Na2SO4, and evaporated. The residue is purified by column chromatography on silca gel to afford an oil which is 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 is then partitioned between CH2Cl2 and water
- customthe layers are separated
- extractionthe aqueous layer is extracted with CH2Cl2
- washwashed with water
- dry with materialdried over Na2SO4
- customevaporated
- customThe residue is purified by column chromatography on silca gel
- customto afford an oil which
- customis crystallized from ether/hexane
- customrecrystallized from ether/hexane
Sources & evidence
- ORD record
- ord-c2949c3f4e1e48d2a6573458833cf0ff
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05942520
Reaction notes
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