Triethylamine → HCID 21309551, compound

HRID 1416472Notes

Reaction equation

HRID 1416472 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:12][C@@H:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]=2)[CH:10]=[CH:9]1.C(N(CC)CC)C.[C:37](Cl)(=[O:46])[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:39]([O:38][C:37]([N:27]1[CH2:26][CH2:25][N:24]([C:16]2[N:15]=[C:14]([O:13][C@@H:11]3[CH2:12][C@H:8]([O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH:9]=[CH:10]3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:29][CH2:28]1)=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 21309555HCID 21309555, compound

Product 1

HCID 21309551HCID 21309551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[(1R,4S)-[4-[(RS)-(tetrahydropyran-2-yl)oxy]cyclopent-2-en-1-yl]oxy]-2-(1-piperazinyl)quinazoline (11.07 g) in dry methylene chloride (110 ml) is added triethylamine (7.75 ml) with stirring under ice-cooling, and thereto is further added dropwise a solution of benzyl chlorocarbonate (4.40 ml) in dry methylene chloride (20 ml). The mixture is stirred under ice-cooling for one hour. The reaction mixture is washed with water, and dried over anhydrous magnesium sulfate. The 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-[(1R,4S)-[4-[(RS)-(tetrahydropyran-2-yl)oxy]cyclopent-2-en-1-yl]oxy]quinazoline (12.57 g) as oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred under ice-
  3. temperaturecooling for one hour
  4. washThe reaction mixture is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solution is evaporated to dryness under reduced pressure
  7. customthe residue is purified by medium pressure liquid column chromatography (eluent, chloroform)

Sources & evidence

ORD record
ord-efe6dca094cb4ae1ace3de94588021cc
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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