Ethyl bromoacetate → Ethyl [6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetate

HRID 2383986Notes

Reaction equation

HRID 2383986 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][NH:20][C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:27]([C:16]1([C:6]2[C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:25][CH2:24][C:23]2[N:22]=[CH:21][N:20]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:19](=[O:26])[C:18]=2[CH2:17]1)#[N:28]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1356204896-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

Product 1

HCID 24804607Ethyl [6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in example 13 (170 mg, 0.46 mmol) in 5 ml of dry DMF was added ethyl bromoacetate (84.5 mg, 0.5 mmol) and cesium carbonate (195.6 mg, 0.6 mmol) at room temperature for 1 hr. Once the reaction has completed, the reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, followed by brine, and concentrated under vacuum. The crude product was purified by column chromatography to get 175 mg (83.2% yields) of the product. MP-106.2-125.1° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by column chromatography
  5. customto get
  6. custom175 mg (83.2% yields) of the product

Sources & evidence

ORD record
ord-d15a430eee7b45aab6022df6551f4cce
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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