Triethylamine → 2-(4-(2-(1-acetylazetidin-3-yl)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 591593Notes

Reaction equation

HRID 591593 reaction equation
N1CC(NC(=[O:8])C)C1.Br[CH2:10][CH2:11][O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]2[NH:29][C:28](=[O:30])[C:27]3[C:22](=[CH:23][C:24]([O:33][CH3:34])=[CH:25][C:26]=3[O:31][CH3:32])[N:21]=2)=[CH:15][C:14]=1[CH3:35].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])C>CN(C=O)C>[C:39]([N:38]1[CH2:36][CH:42]([CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[NH:29][C:28](=[O:30])[C:27]4[C:22](=[CH:23][C:24]([O:33][CH3:34])=[CH:25][C:26]=4[O:31][CH3:32])[N:21]=3)=[CH:15][C:14]=2[CH3:35])[CH2:41]1)(=[O:8])[CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13401968N-(azetidin-3-yl)acetamideHCID 1364005142-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one

Product 1

HCID 1363480452-(4-(2-(1-acetylazetidin-3-yl)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-azetidin-3-yl-acetamide (17) (1.99 mmol) and 2-[4-(2-bromo-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (18) (1.00 mmol) in anhydrous DMF (10 mL) was added triethylamine (3 mL). The reaction mixture was stirred at room temperature for 3 days under nitrogen. The solvent was evaporated under reduced pressure, water (50 mL) was added, and the precipitated solid was filtered off. The aqueous layer was extracted with ethyl acetate (2×100 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by the Simpliflash system (0-5% 7 N ammonia in methanol and CH2Cl2 as eluent) to give the title compound 19 as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, water (50 mL)
  2. additionwas added
  3. filtrationthe precipitated solid was filtered off
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe crude compound was purified by the Simpliflash system (0-5% 7 N ammonia in methanol and CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-3f5a937688d94a7bb6c4e7aa801fa073
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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