Pyridine → HCID 178502064, compound

HRID 2356708Notes

Reaction equation

HRID 2356708 reaction equation
[NH2:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[C:26]([Cl:30])(=[O:29])[O:27][CH3:28].C(OCC)C>C(Cl)Cl>[ClH:30].[CH3:28][O:27][C:26]([NH:1][C:2]1[NH:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6586Methyl chloroformateHCID 178509086HCID 178509086, compound

Product 1

HCID 178502064HCID 178502064, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-(4-fluorophenyl)-4-phenylimidazole (63 mg) and pyridine (40 mg) in methylene chloride (5 ml) was added methyl chlorocarbonate (28 mg) under ice-cooling and the mixture was stirred at room temperature overnight. To the reaction mixture was added diethyl ether, and the solvent was removed under reduced pressure. The resulting residue was triturated with diethyl ether and the powder was collected by filtration. The powder was treated with hydrogen chloride-methanol solution to obtain 5-methoxycarbonylamino-2-(4-fluorophenyl)-4-phenylimidazole hydrochloride (67 mg) as colorless powder.

Workup

  1. temperaturecooling
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting residue was triturated with diethyl ether
  4. filtrationthe powder was collected by filtration
  5. additionThe powder was treated with hydrogen chloride-methanol solution

Sources & evidence

ORD record
ord-946a2ecb889e45008c1250d2b1d39e56
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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