Methanol → HCID 20780216, compound

HRID 1246315Notes

Reaction equation

HRID 1246315 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-48f58415524b4b3fa775d0f49c6ce96d
Source dataset
uspto-grants-2006_10
Patent number
US07125990B2

Reaction notes

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