Water → HCID 23151223, compound

HRID 2386954Notes

Reaction equation

HRID 2386954 reaction equation
CS(O[CH:6]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[C:19]3[CH3:29])=[CH:14][CH:13]=2)[CH2:7]1)(=O)=O.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:29][C:19]1[N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH:8]3[CH2:9][CH2:10][CH:6]([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:7]3)=[CH:13][CH:14]=2)[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 23151392HCID 23151392, compound

Product 1

HCID 23151223HCID 23151223, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-[4-({3-[(methylsulfonyl)oxy]cyclopentyl}oxy)phenyl]-2-methyl -4(3H)-quinazolinone (550 mg, 1.33 mmol), pyrrolidine (474 mg, 6.7 mmol) and potassium carbonate (277 mg, 2.0 mmol) were mixed in dimethylformamide (10 mL) and stirred at 80° C. overnight. Distilled water was added, and the mixture extracted with ethyl acetate. The organic phase was dried by anhydrous magnesium sulfate, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to obtain the title compound (143 mg) as a colorless solid. 2-methyl-3-[4-{[3-(1-pyrrolidinyl)cyclopentyl]oxy}phenyl]-4(3H)-quinazolinone (trans isomer)

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialThe organic phase was dried by anhydrous magnesium sulfate
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-f235e380d95b4251a49031de5206c87e
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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