HCID 16070453, compound → HCID 16070834, compound

HRID 1710721Notes

Reaction equation

HRID 1710721 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:9]1[C:10]([NH2:26])=[N:11][C:12]([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:14]=1)#[CH:8]>CN1CCCC1=O>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[C:12]1[N:11]=[C:10]2[NH:26][CH:8]=[CH:7][C:9]2=[N:14][C:13]=1[C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 16070453HCID 16070453, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 16070834HCID 16070834, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A mixture of potassium t-butoxide (45 mg, 0.40 mmol) in N-methylpyrrolidone (1 mL) was stirred under nitrogen and a solution of 3-ethynyl-6-(2-furyl)-5-pyridin-4-ylpyrazin-2-amine (Example 65, 50 mg, 0.19 mmol) in N-methylpyrrolidone (1 mL) was added. The mixture was stirred at room temperature overnight, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic extracts washed with water and brine, dried (MgSO4) and concentrated under vacuum. Silica gel flash column chromatography (dichloromethane/methanol 95:5) gave the title compound as a yellow solid (20 mg, 40%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. custompartitioned between water and ethyl acetate
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washthe organic extracts washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b3177a60690742b2afbd5394ed18f248
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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