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Triethylamine → HCID 67582301, compound

HRID 1416467
Notes
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Reaction equation

HRID 1416467 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:9][C@H:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:12]=2)[CH:7]=[CH:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:34](Cl)(=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:9][C@H:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([N:21]3[CH2:22][CH2:23][N:24]([C:34]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:43])[CH2:25][CH2:26]3)[N:12]=2)[CH:7]=[CH:6]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 56991092HCID 56991092, compound

Product 1

HCID 67582301HCID 67582301, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344Dichloromethane
Solvent
2×

Procedure

To a solution of 4-[(1S,4R)-(4-acetoxycyclopent-2-en-1-yl)oxy]-2-(1-piperazinyl)quinazoline (2.07 g) in dry methylene chloride (15 ml) is added triethylamine (1.63 ml) with stirring under ice-cooling, and thereto is further added dropwise a solution of benzyl chlorocarbonate (0.92 ml) in dry methylene chloride (5 ml). The mixture is stirred under ice-cooling for 2 hours, and the reaction mixture is diluted with chloroform, 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 4-[(1S,4R)-(4-acetoxycyclopent-2-en-1-yl)oxy]-2-[4-(benzyloxycarbonyl)piperazin-1-yl]quinazoline (2.36 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred under ice-
  3. temperaturecooling for 2 hours
  4. washwashed 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-4969246ec07c47ea9b22fa665765f662
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05912247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes