Water → Tert-butyl 3-{[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]amino}propylcarbamate

HRID 547455Notes

Reaction equation

HRID 547455 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20](Br)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[C:32]([NH:39][CH2:40][CH2:41][CH2:42][NH2:43])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].O>C(OCC)(=O)C>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([NH:43][CH2:42][CH2:41][CH2:40][NH:39][C:32](=[O:33])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 58378174HCID 58378174, compound

Product 1

HCID 58378184Tert-butyl 3-{[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]amino}propylcarbamateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-bromo-N,N-dimethylacetamide (1.4 g, 1 eq.) in of N,N-dimethylformamide (10 ml), was added N-Boc-1,3-diaminopropane (2.8 g, 5 eq.). The reaction was stirred at room temperature for 4 h and then heated to 40° C. The mixture was stirred at 40° C. overnight. Water and ethyl acetate were added to the mixture. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography to give tert-butyl 3-{[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]amino}propylcarbamate (1 g) as a pale yellow solid.

Workup

  1. temperatureheated to 40° C
  2. stirringThe mixture was stirred at 40° C. overnight
  3. washThe organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-39bc120e182949088fc2b0cd7c420302
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Reaction notes

Loading…