Triethylamine → HCID 10873678, compound

HRID 1416465Notes

Reaction equation

HRID 1416465 reaction equation
[CH:1]1([O:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:8]=2)[CH2:5][CH2:4][CH:3]=[CH:2]1.C(N(CC)CC)C.[C:30](Cl)(=[O:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:32]([O:31][C:30]([N:20]1[CH2:19][CH2:18][N:17]([C:9]2[N:8]=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH:3]=[CH:2]3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:22][CH2:21]1)=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22375260HCID 22375260, compound

Product 1

HCID 10873678HCID 10873678, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[(cyclopent-2-en-1-yl)oxy]-2-(1-piperazinyl) quinazoline (1.47 g) in dry methylene chloride (15 ml) is added triethylamine (1.39 ml) with stirring under ice-cooling, and thereto is further added dropwise a solution of benzyl chlorocarbonate (0.75 ml) in dry methylene chloride (3 ml). The mixture is stirred at 0° C. for 4 hours, and the reaction mixture is diluted with chloroform and washed with water, and then dried over anhydrous magnesium sulfate. The resulting solution is evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography (eluent, chloroform) to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(cyclopent-2-en-1-yl)oxy]quinazoline (1.85 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at 0° C. for 4 hours
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe resulting solution is evaporated to dryness under reduced pressure
  6. customthe residue is purified by medium pressure liquid column chromatography (eluent, chloroform)

Sources & evidence

ORD record
ord-a058a2eaba414236983c54cb302d97cd
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

Loading…