1,1'-Carbonyldiimidazole → HCID 10460533, compound

HRID 496030Notes

Reaction equation

HRID 496030 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N:35]1([C:41]([C:43]2[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH3:52])=[C:45]([O:53][CH3:54])[CH:44]=2)=[O:42])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([N:38]2[CH2:39][CH2:40][N:35]([C:41](=[O:42])[C:43]3[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH3:52])=[C:45]([O:53][CH3:54])[CH:44]=3)[CH2:36][CH2:37]2)=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 28742041-(3,4,5-Trimethoxybenzoyl)piperazineHCID 22324250HCID 22324250, compound

Product 1

HCID 10460533HCID 10460533, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6,6-bis-(4-fluoro-phenyl)-hex-5-enoic acid (2.64 g, 8.75 mmol) and CDI (1.42 g, 8.75 mmol) in dry THF (30 ml) was stirred for 1 hr at room temperature under nitrogen. A solution of piperazin-1-yl-(3,4,5,-trimethoxy-phenyl)-methanone (2.45 g, 8.75 mmol) in dry THF (30 ml) was added to above solution and resulting mixture stirred at room temperature overnight. The mixture is diluted with EtOAc (30 ml) and washed with water (2×30 ml) and dried over MgSO4. Evaporation of solvent followed by column chromatography using CH2Cl2:MeOH (15:1) gave the desired product in 49% yield.

Workup

  1. customresulting mixture
  2. washwashed with water (2×30 ml)
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-4b0498969d044fd5819a2fd5ff066957
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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