Methyl iodide → 6-Chloro-1,4-dimethyl-3-oxo-1,3-dihydro-pyrazolo[3,4-b]pyridine-2-carboxylic acid 2-methylbenzylamide

HRID 1685222Notes

Reaction equation

[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][C:12]([Cl:19])=[CH:13][C:14]=2[CH3:18])[NH:9]1)=[O:7].[CH3:24]C(C)([O-])C.[K+].IC.C(N(CC)CC)C>C1COCC1>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][C:12]([Cl:19])=[CH:13][C:14]=2[CH3:18])[N:9]1[CH3:24])=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

99.89 mg (0.3 mmol) of 6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid 2-methylbenzylamide and 37.3 mg (0.33 mmol) of potassium tert-butoxide were stirred in 10 ml of THF at room temperature for 10 minutes. Addition of 20.7 μl of iodomethane was followed by stirring at room temperature for 2 h and at 60° C. for 4 h. Then 30 μl of iodomethane and 50 μl of triethylamine were added, and stirring was continued at 60° C. for 7 h, the mixture was concentrated and mixed with water and ethyl acetate, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 18 mg (17%), M+H+: 345.08.

Workup

stirringstirring
waitwas continued at 60° C. for 7 h
concentrationthe mixture was concentrated
additionmixed with water and ethyl acetate
customthe organic phase was separated off
concentrationconcentrated
custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record: ord-6eb2ec6b34804d0dadc8fb9448c4d4d2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148395B2

Reaction notes

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