Triethylamine → HCID 178425874, compound

HRID 547460Notes

Reaction equation

HRID 547460 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[NH:7][C:8]([CH:12]([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[N:9]2)=[CH:4][CH:3]=1.[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.C(N([CH2:46][CH3:47])CC)C>>[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([O:30][CH:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([CH:12]([N:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:29])[C:6](=[O:30])[C:5]3[CH:10]=[CH:11][C:46]([CH3:47])=[CH:3][CH:4]=3)[C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[NH:7]2)=[O:37])=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 136004604HCID 136004604, compound

Product 1

HCID 178425874HCID 178425874, compound

Procedure

To a solution of tert-butyl 3-{[1-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]amino}propylcarbamate (1.2 g, 1 eq.) methylene chloride 920 ml) at 0° C., was added 4-methyl benzoyl chloride (1.1 ml, 3 eq.) and triethylamine (1.9 ml, 5 eq.). The reaction was allowed to warm up to room temperature and stirred at room temperature overnight. The solvent was evaporated and the crude product was dissolved in ethyl acetate. Ethyl acetate layer was washed with water, saturated sodium carbonate, saturated sodium chloride, dried over magnesium sulfate, filtered, and evaporated to yield 2-[1-[{3-[(tert-butoxycarbonyl)amino]propyl} (4-methylbenzoyl)amino]-2-(dimethylamino)-2-oxoethyl]-7-chloro-3,4-dihydroquinazolin-4-yl 4-methylbenzoate (2.3 g) as a brown oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product was dissolved in ethyl acetate
  3. washEthyl acetate layer was washed with water, saturated sodium carbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6491e86baed44d76bda9a561513e1770
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Reaction notes

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