Methanol → HCID 20780216, compound

HRID 1295858Notes

Reaction equation

HRID 1295858 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([Br:15])=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].Br[CH2:17][C:18]([NH:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=1[CH3:29])=[O:19].C1CCN2C(=NCCC2)CC1.CO>C1(C)C=CC=CC=1.CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:17][C:18](=[O:19])[NH:20][C:21]2[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])[C:8]([Br:15])=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21916126HCID 21916126, compoundHCID 178470342HCID 178470342, compound

Product 1

HCID 20780216HCID 20780216, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-5-trifluoromethyl-3H-imidazole-4-carboxylic acid ethyl ester (3.00 g, 10.45 mmol) and 2-bromo-N-(2,4,6-trimethyl-phenyl)-acetamide (2.94 g, 11.50 mmol) in a mixture of toluene (16 mL) and acetone (8 mL) was added DBU (1.72 mL, 11.50 mmol). The resulting solution was stirred at room temperature for 5 days. Methanol (10 mL) was added to dissolve the precipitate formed, followed by the addition of silica gel (25 g). The solvent was removed under reduced pressure to dryness and the residue was applied to a silica gel-packed column. The isolation of the product was achieved by column chromatography (hexanes-ethyl acetate 4:1). Yield—4.25 g (88%). LC/MS: tR=1.62 min., MS: [M+H]=462.

Workup

  1. dissolutionto dissolve the precipitate
  2. customformed
  3. additionfollowed by the addition of silica gel (25 g)
  4. customThe solvent was removed under reduced pressure to dryness

Sources & evidence

ORD record
ord-d286682de1234357a700e0fef5858869
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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