Water → HCID 66733107, compound

HRID 1966830Notes

Reaction equation

HRID 1966830 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:10]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:11]=3[N:12]=[CH:13][C:14]=2[C:15]2[CH2:19][C:18]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[O:17][N:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH3:36]Cl.[CH2:38]1[CH2:40][CH2:39]1.O>CN(C)C=O>[CH:2]1([NH:8][C:9]2[C:10]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:11]=3[N:12]=[CH:13][C:14]=2[C:15]2[CH2:19][C:18]3([CH2:24][CH2:23][N:22]([CH2:36][CH:38]4[CH2:40][CH2:39]4)[CH2:21][CH2:20]3)[O:17][N:16]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20280621HCID 20280621, compoundHCID 66732657HCID 66732657, compound

Product 1

HCID 66733107HCID 66733107, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

N-cyclohexyl-1-ethyl-5-(1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine hydrochloride salt (70 mg, 0.00016 mole) (example 22) was taken in dimethylformamide (5 ml). Potassium carbonate (69 mg, 0.00050 mole) and cyclopropane methyl chloride (0.20 ml, 0.000021 mole) were added. The reaction mixture was stirred at 70-80° C. overnight. Water was added and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuum. The crude product obtained was purified by preparative thin layer chromatography.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1e3c9a7804bd4efd9b5564b911ab2cb2
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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