Water → HCID 23151392, compound

HRID 2111844Notes

Reaction equation

HRID 2111844 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:23](=[O:24])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[C:15]3[CH3:25])=[CH:10][CH:9]=2)[CH2:3]1.C(N(CC)CC)C.[S:33](Cl)([CH3:36])(=[O:35])=[O:34].O>C(Cl)Cl>[CH3:36][S:33]([O:1][CH:2]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:23](=[O:24])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[C:15]3[CH3:25])=[CH:10][CH:9]=2)[CH2:3]1)(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23151270HCID 23151270, compound

Product 1

HCID 23151392HCID 23151392, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{4-[(3-hydroxycyclopentyl)oxy]phenyl}-2-methyl-4(3H)-quinazolinone (520 mg, 1.19 mmol) and triethylamine (0.33 mL, 2.32 mmol) were mixed in methylene chloride and cooled on an ice bath. Mesyl chloride (0.12 mL, 1.55 mmol) was dripped in and stirred for 10 minutes at room temperature. Distilled water was added to the reaction mixture, and the mixture extracted with ethyl acetate. The organic phase was washed with distilled water, and dried by anhydrous magnesium sulfate. The residue was concentrated to dryness, and the target compound (553 mg) was thus obtained.

Workup

  1. temperaturecooled on an ice bath
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic phase was washed with distilled water
  4. dry with materialdried by anhydrous magnesium sulfate
  5. concentrationThe residue was concentrated to dryness

Sources & evidence

ORD record
ord-533ad5ba96b14b3c8be395c3846eac73
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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