Potassium Carbonate → HCID 58801629, compound

HRID 2253407Notes

Reaction equation

HRID 2253407 reaction equation
Cl.[CH2:2]([C:4]1[C:12]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH2:2]([C:4]1[C:12]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68886250HCID 68886250, compound

Product 1

HCID 58801629HCID 58801629, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochloride (10.3 g, 35 mmol) and potassium carbonate (5.8 g) in ethyl acetate (150 mL) and water (30 mL) was stirred for 8 minutes at room temperature. The organic extract was separated and then washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to afford N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine (9.1 g). This compound was dissolved in tetrahydrofuran (180 mL), and then cyclopropanecarbaldehyde (7.4 g, 106 mmol) and sodium triacetoxyborohydride (10.5 g, 49.7 mmol) were added and the reaction mixture was stirred for 10 minutes. After completion of the reaction, ethyl acetate (400 mL) and water (200 mL) were added to the reaction mixture and the organic extract was separated. After extracting the aqueous layer again with ethyl acetate (200 mL), the organic extracts were combined and washed with water (100 mL) and brine (100 mL). The organic extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to afford 11.9 g of the title compound as a yellow oil (≧99% yield).

Workup

  1. extractionThe organic extract
  2. customwas separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-aba5ddfb3ecf48f9bb407f80021cdbba
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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