Dicyclohexylcarbodiimide → HCID 178489895, compound

HRID 599547Notes

Reaction equation

HRID 599547 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][C:33]([N:36]4[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37]4)=[C:32]([O:42][CH3:43])[CH:31]=3)=[N:25][C:24]=2[C:44]([OH:46])=[O:45])=[CH:19][CH:18]=1.[Br:47][CH2:48][CH2:49]O.O.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[NH:27][C:26](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][C:33]([N:36]4[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37]4)=[C:32]([O:42][CH3:43])[CH:31]=3)=[N:25][C:24]=2[C:44]([O:46][CH2:49][CH2:48][Br:47])=[O:45])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 108982-BromoethanolHCID 86585896Sodium bicarbonate waterHCID 178489893HCID 178489893, compound

Product 1

HCID 178489895HCID 178489895, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DCC (47 mg) was added to a solution of 5-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1H-imidazole-4-carboxylic acid (80 mg) and 2-bromoethanol (0.27 mL), DMAP (5 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for 15 hours. Then, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 27 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-aa90827616e74e1ea561a0607c156b63
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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