Tetrahydrofuran → HCID 21084180, compound

HRID 2253405Notes

Reaction equation

HRID 2253405 reaction equation
[CH2:1]([C:3]1[C:11]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].CC(C)([O-])C.[K+].CS(O[CH2:31][CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)(=O)=O.O1CCCC1>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([C:3]1[C:11]([N:12]([CH2:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 21084179HCID 21084179, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21084180HCID 21084180, compoundYield 108.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)carbamate (12 g, 46 mmol) and potassium tert-butoxide (6.2 g, 55 mmol) dissolved in N,N-dimethylformamide (120 mL) was added tetrahydropyran-4-ylmethyl methanesulfonate (10.7 g, 55 mmol) while cooling with ice, the reaction mixture was stirred for 1 hour, and then tetrahydrofuran (200 mL) was further added and the reaction mixture was additionally stirred for 18 hours. Water (200 mL) and ethyl acetate (500 mL) were then added to the reaction mixture, and the aqueous layer was separated and extracted with ethyl acetate (300 mL). The combined organic extracts were washed with water (300 mL, 3 times) and brine, dried over magnesium sulfate and evaporated under reduced pressure to afford 18 g of the title compound as a yellow oil (≧99% yield).

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe reaction mixture was additionally stirred for 18 hours
  3. customthe aqueous layer was separated
  4. extractionextracted with ethyl acetate (300 mL)
  5. washThe combined organic extracts were washed with water (300 mL, 3 times) and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d3347748da4944d7b42acea6446e052c
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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