Potassium Carbonate → 2-[(R)-1-(3-Phthalimido-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one

HRID 490266Notes

Reaction equation

HRID 490266 reaction equation
[NH2:1][C@@H:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33](=[O:46])[CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45]>CN(C=O)C>[C:36]1(=[O:45])[N:35]([CH2:34][C:33](=[O:46])[CH2:32][NH:1][C@@H:2]([C:6]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:14](=[O:23])[C:13]3[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=3)[N:7]=2)[CH:3]([CH3:5])[CH3:4])[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 21015281(R)-2-(1-amino-2-methylpropyl)-3-benzyl-7-chloroquinazolin-4(3H)-one

Product 1

HCID 690735002-[(R)-1-(3-Phthalimido-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-((R)-1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (5.0 g, 14.6 mMol) and K2CO3 (2.1 g, 15.2 mMol) in DMF (50 mL) was added N-(3-Bromo-2-oxopropyl)-phthalimide (4.5 g, 14.8 mMol) (Nair et al.; J. Org. Chem.; 40; 1975; 1745). The reaction was stirred at RT for 3 h, concentrated under vacuum, taken up in EtOAc, washed with water, brine, dried (Na2SO4) and evaporated to give the title compound (7.94 g, 14.6 mMol) as an off-white solid: MS (ES) m/e 543.2 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-21d76c65fa94460fa329bd6a9e3e6037
Source dataset
uspto-grants-2009_05
Patent number
US07528137B2

Reaction notes

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