Water → HCID 136004604, compound

HRID 547459Notes

Reaction equation

HRID 547459 reaction equation
Br[CH:2]([C:8]1[NH:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][C:12]([Cl:19])=[CH:13][CH:14]=2)[N:9]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[C:20]([NH:27][CH2:28][CH2:29][CH2:30][NH2:31])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].O.C(OCC)(=O)C>CN(C)C=O>[Cl:19][C:12]1[CH:11]=[C:10]2[C:15]([C:16](=[O:18])[NH:17][C:8]([CH:2]([NH:31][CH2:30][CH2:29][CH2:28][NH:27][C:20](=[O:21])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:3]([N:5]([CH3:7])[CH3:6])=[O:4])=[N:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 136004603HCID 136004603, compound

Product 1

HCID 136004604HCID 136004604, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-2-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide (950 mg, 1 eq.) in N,N-dimethylformamide (10 ml), was added N-Boc-1,3-diaminopropane (2.4 g, 5 eq.). The reaction was stirred at 60° C. for 30 minutes. Water and ethyl acetate was added. Ethyl acetate layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated to give tert-butyl 3-{[1-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]amino}propylcarbamate (1.2 g) as a pale orange solid.

Workup

  1. washEthyl acetate layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1295be06a7634b10a2f21f091c00d61a
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Reaction notes

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