4-(Aminomethyl)cyclohexan-1-ol → 1-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375881Notes

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]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2].[OH:19][CH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[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:23]4[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline (2.02 g, 15.5 mmol), DMSO (6 ml) and 4-hydroxy cyclohexylmethylamine (2 g, 15.5 mmol) was heated at 110° C. overnight. The reaction mixture was partitioned between CH2Cl2 /water/NaHCO3, and the CH2Cl2 layer was separated, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford 1.8 g of 1-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl) -1H-pyrazolo[3,4-b]quinolin-4-amine.

Workup

customThe reaction mixture was partitioned between CH2Cl2 /water/NaHCO3
customthe CH2Cl2 layer was separated
dry with materialdried over MgSO4
customevaporated
customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record: ord-44bba0110f8042dc959acf1281e6b1a1
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488055

Reaction notes

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