Potassium Hydroxide → HCID 58574392, compound

HRID 1619296Notes

Reaction equation

HRID 1619296 reaction equation
CS(O[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[F:19][C:20]1[CH:21]=[C:22]([C:26]#[C:27][C:28]2[CH:37]=[C:36]3[C:31]([C:32](=[O:38])[NH:33][CH:34]=[N:35]3)=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=1.[OH-].[K+]>O1CCOCC1.[Na+].[Cl-]>[F:19][C:20]1[CH:21]=[C:22]([C:26]#[C:27][C:28]2[CH:37]=[C:36]3[C:31]([C:32](=[O:38])[N:33]([CH2:6][CH:7]4[CH2:11][CH2:10][CH2:9][N:8]4[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:34]=[N:35]3)=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 18007568Tert-butyl 2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylateHCID 136038173HCID 136038173, compound

Product 1

HCID 58574392HCID 58574392, compoundYield 290.1%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate (0.86 g, 3.42 mmol, 5.4 equiv) and 7-((3-fluorophenyl)ethynyl)quinazolin-4(3H)-one (0.15 g, 0.57 mmol, 1 equiv) in 1,4-dioxane (10 mL) was added KOH (0.38 g, 6.98 mmol, 12 equiv). The reaction mixture was stirred at reflux overnight. After it was cooled to room temperature, the reaction mixture was diluted with saturated NaCl and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give 0.74 g of the desired product. MS (ESI): 448 (MH+).

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1d59ddf7b726426a88b82fbc886cd120
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…