Cyclohexanemethylamine → 1-ethyl-6-(methylsulfinyl)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine
Reaction equation
[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]Participants
Conditions
- Temperature
- 110 °C
Procedure
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.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customwas partitioned between CHCl3 (20 mL) and water (20 mL)
- additioncontaining NH4OH (3 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with CH2Cl2 (10 mL)
- dry with materialthe organic layers were combined dried over MgSO4
- customevaporated
- customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
- customfollowed by recrystallization from ethyl acetate (2×)
Sources & evidence
- ORD record
- ord-d36773cf84eb4c38b7859f21c5d24564
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488055
Reaction notes
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