Water → HCID 57964907, compound

HRID 1931726Notes

Reaction equation

HRID 1931726 reaction equation
[H-].[Na+].[N+]([C:6]1[CH:11]=C[C:9]([O:12][C:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([O:30][C:31]5[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=5)=[C:24]4[CH:23]=[N:22]3)[CH2:17][CH2:16]2)=[O:14])=[CH:8][CH:7]=1)([O-])=O.C1(O)CCCC1.O>O1CCCC1>[CH:9]1([O:12][C:13]([N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([O:30][C:31]5[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=5)=[C:24]4[CH:23]=[N:22]3)[CH2:19][CH2:20]2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 57964982HCID 57964982, compound

Product 1

HCID 57964907HCID 57964907, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil; 6 mg, 0.15 mmol) was added to a solution of 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid 4-nitro-phenyl ester (Example 123; 37 mg, 0.078 mmol) in anhydrous tetrahydrofuran (750 μL) under argon. Cyclopentanol (70 μL, 0.77 mmol) was added and the mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (sodium sulfate), filtered, evaporated, and purified on an Isco 4 g column, eluting with 0-4% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid cyclopentyl ester (6 mg, 18%). Mass spectrum (ES) MH+=423.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified on an Isco 4 g column
  6. washeluting with 0-4% methanol/dichloromethane

Sources & evidence

ORD record
ord-73c572e417664905a0b63e2c74191e5e
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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