1,1'-Carbonyldiimidazole → HCID 10479297, compound

HRID 1819957Notes

Reaction equation

HRID 1819957 reaction equation
[CH2:1]([C:3]([C:21]1[S:25][C:24]([C:26]([NH:28][NH2:29])=[O:27])=[C:23]([CH3:30])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32]>C1COCC1.CCOC(C)=O>[CH2:1]([C:3]([C:21]1[S:25][C:24]([C:26]2[O:27][C:31](=[O:32])[NH:29][N:28]=2)=[C:23]([CH3:30])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 68625394HCID 68625394, compound

Product 1

HCID 10479297HCID 10479297, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid hydrazide (432 mg, 1 mmol), 1,1′-carbonyldiimidazole (405 mg, 2.5 mmol) and triethylame (0.28 ml, 2 mmol) in THF (10 ml) is stirred at reflux overnight. It is diluted with EtOAc, washed with 1N HCl solution. The organic phase is concentrated and chromatographed (Hex to 20% EtOAc/Hex to give the title compound (290 mg, 63%).

Workup

  1. temperatureat reflux overnight
  2. washwashed with 1N HCl solution
  3. concentrationThe organic phase is concentrated
  4. customchromatographed (Hex to 20% EtOAc/Hex

Sources & evidence

ORD record
ord-a2ea773e1dc648a78757a9248b8a4634
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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