Cyclohexylamine → ethyl 4-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1966802Notes

Reaction equation

[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]2[N:20]([CH2:23][CH3:24])[N:21]=[CH:22][C:10]=12>C(#N)C>[CH:1]1([NH:7][C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]3[N:20]([CH2:23][CH3:24])[N:21]=[CH:22][C:10]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

Cyclohexyl amine (9.07 ml, 0.7905 mole) was added to a mixture of ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (10 gm, 0.0395 mole) (example 3) in acetonitrile. After stirring for about 2 h at 110° C., acetonitrile was removed under reduced pressure. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo to give brownish solid.

Workup

customacetonitrile was removed under reduced pressure
additionWater was added
extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated in vacuo
customto give brownish solid

Sources & evidence

ORD record: ord-46412d01f50f48dda4dae1df5fd9a5de
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420666B2

Reaction notes

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