Ethyl chloroformate → HCID 21851293, compound

HRID 617155Notes

Reaction equation

HRID 617155 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:16]=2)[CH2:11][CH2:10]1)=[O:5].[C:40](Cl)(=[O:44])[O:41][CH2:42][CH3:43]>>[CH2:42]([O:41][C:40]([NH:1][C:2]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:16]=2)[CH2:11][CH2:10]1)=[O:5])=[O:44])[CH3:43]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 21851296HCID 21851296, compound2×

Product 1

HCID 21851293HCID 21851293, compound

Procedure

Ethyl chlorocarbonate (10 ml) was added to 540 mg (1.01 mmol) of 4-[2-(2-amino-5-methylbenzoylamino)ethyl]-1-(6,7-dimethoxy-2-morpholino-4-quinazolinyl)piperidine (Compound 1) obtained in Reference Example 13, and the mixture was heated under reflux for 10 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure, followed by addition of hexane and ether to the residue. The precipitated crystals were collected by filtration to give 430 mg of crude 4-[2-(2-ethoxycarbonylamino-5-methylbenzoylamino)ethyl]-1-(6,7-dimethoxy-2-morpholino-4-quinazolinyl)piperidine, which was then dissolved in 10 ml of ethanol. To the solution was added 210 mg of potassium hydroxide, and the mixture was heated under reflux for one hour. After evaporation of the solvent under reduced pressure, water was added to the residue, followed by extraction with chloroform. The organic layer was washed and dried, and the solvent was evaporated to give 360 mg (overall yield: 64%) of Compound 29 as white crystals.

Workup

  1. customobtained in Reference Example 13
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 10 hours
  4. customthe solvent was evaporated under reduced pressure
  5. additionfollowed by addition of hexane and ether to the residue
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-b68afc7aaea34e429769558702420147
Source dataset
uspto-grants-1999_09
Patent number
US05948784

Reaction notes

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