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
4
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) is heated at 110° C. over night. The reaction mixture is cooled to room temperature, then is partitioned between CHCl3 (20 ml) and water (20 ml) containing NH4OH (3 ml). The layers are separated, the aqueous layer is extracted with CH2Cl2 (10 ml), and the organic layers are combined dried over MgSO4 and evaporated. The residue is 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 is cooled to room temperature
- customis partitioned between CHCl3 (20 ml) and water (20 ml)
- additioncontaining NH4OH (3 ml)
- customThe layers are separated
- extractionthe aqueous layer is extracted with CH2Cl2 (10 ml)
- dry with materialthe organic layers are combined dried over MgSO4
- customevaporated
- customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate
- customfollowed by recrystallization from ethyl acetate (2×)
Sources & evidence
- ORD record
- ord-081daccbb8aa4eeca574ff1b16c6e607
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05942520
Reaction notes
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