Sodium Bicarbonate → HCID 44622155, compound

HRID 1931697Notes

Reaction equation

HRID 1931697 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[N:5]=[CH:4][N:3]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([NH:31][NH2:32])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH2:27][CH:28]([N:31]2[C:2]3=[N:3][CH:4]=[N:5][C:6]([O:10][C:11]4[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=4)=[C:7]3[CH:8]=[N:32]2)[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 56965816HCID 56965816, compound2×HCID 57964920HCID 57964920, compound2×

Product 1

HCID 44622155HCID 44622155, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-6-(2-methyl-pyridin-3-yloxy)-pyrimidine-5-carbaldehyde (Intermediate 18; 515 mg, 2.1 mmol) and 4-hydrazino-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 9; 688 mg, 3.2 mmol) in toluene (5 mL) was heated at reflux overnight. Aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The organic phases were evaporated and purified on an Isco 40 g column, eluting with 0-3% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (330 mg, 38%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic phases were evaporated
  5. custompurified on an Isco 40 g column
  6. washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-1ac88e09eafe428799e985b52cf4b646
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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