Acetyl chloride → HCID 11690616, compound

HRID 2111825Notes

Reaction equation

HRID 2111825 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=1)[C:5]2=[O:29].[C:30](Cl)(=[O:32])[CH3:31].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.N1C=CC=CC=1>[C:30]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:17][CH:18]=1)[C:5]2=[O:29])(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 23151376HCID 23151376, compound

Product 1

HCID 11690616HCID 11690616, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-amino-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}-4(3H)-quinazolinone (228 mg, 0.58 mmol) were dissolved in a mixed solvent of dry tetrahydrofuran (5 mL) and dry pyridine (1 mL), and coooled on an ice bath. Acetyl chloride (68 mg, 0.87 mmol) was dripped in, and the mixture stirred at room temperature overnight. Ethyl acetate and 1N sodium hydroxide aqueous solution were added, the mixture was extracted with ethyl acetate, and the organic phase was dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (chloroform/methanol=20/1), and the title compound (156 mg, 62%) was obtained as colorless crystals by recrystallization from diethyl ether/heptane.

Workup

  1. customcoooled on an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried with anhydrous sodium sulfate
  4. customThe product was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-4921fce4307641d5b7a711dcf5e7aaca
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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