HCID 20780214, compound → HCID 20780237, compound

HRID 1295854Notes

Reaction equation

HRID 1295854 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:13][C:14](=[O:25])[NH:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:8](Br)=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2]>S1(CCCC1)(=O)=O.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:3][C:4]([C:6]1[N:7]2[CH2:13][C:14](=[O:25])[N:15]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[C:8]2=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 20780214HCID 20780214, compound

Product 1

HCID 20780237HCID 20780237, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 2-bromo-5-methyl-3-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-3H-imidazole-4-carboxylic acid ethyl ester (17.4 mg, 0.038 mmol) and silver carbonate (11.6 mg, 0.042 mmol) in sulfolane (0.5 mL) was heated at 150° C. for 4 h. The resulting reaction mixture was cooled to room temperature and filtered through a short pad of celite. The final purification was achieved by a reverse-phase preparative HPLC to give the desired product as white solid. Yield—12.2 mg (73%). 1H NMR (DMSO d-6, 500 MHz) δ 7.04 (s, 2H), 4.99 (s, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.34 (s, 3H), 2.30 (s, 3H), 2.06 (s, 6H), 1.31 (t, J=7.2 Hz, 3H); LC/MS: tR=1.75 min., MS: [M+H]=328.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered through a short pad of celite
  4. customThe final purification

Sources & evidence

ORD record
ord-dfa139e2788c4c288ceef35096b511ed
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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