3,3-Diethyl-4-[4-(4-methylpiperazine-1-carbonyl)phenoxy]azetidin-2-one → HCID 22614062, compound

HRID 842427Notes

Reaction equation

HRID 842427 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]3[NH:18][C:17](=[O:19])[C:16]3([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[CH2:26]([O:33][C:34]([C:36]1[CH:45]=[CH:44][C:39]([CH2:40][N:41]=[C:42]=[O:43])=[CH:38][CH:37]=1)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]3[N:18]([C:42]([NH:41][CH2:40][C:39]4[CH:44]=[CH:45][C:36]([C:34]([O:33][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:35])=[CH:37][CH:38]=4)=[O:43])[C:17](=[O:19])[C:16]3([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 98845843,3-Diethyl-4-[4-(4-methylpiperazine-1-carbonyl)phenoxy]azetidin-2-oneHCID 22614049HCID 22614049, compound

Product 1

HCID 22614062HCID 22614062, compound

Procedure

According to the method of Shrenik et al (J. Med. Chem., 35, 3745-3754 (1992)), 4-[4-[[(4-methyl)piperazin-1-yl]carbonyl]phenoxy]-3,3-diethyl-2-azetidinone (160 mg, 0.463 mmol) and 4-(benzyloxycarbonyl)benzylisocyanate (261 mg, 0.98 mmol) gave, following purification by flash column chromatography (MeOH/EtOAc, 1:4), the title compound (171 mg, 60%) as an oil.

Workup

  1. customgave
  2. custompurification by flash column chromatography (MeOH/EtOAc, 1:4)

Sources & evidence

ORD record
ord-523ad01fc647438db2c92f13c4f984cc
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

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