1,1'-Carbonyldiimidazole → HCID 18509897, compound

HRID 1370111Notes

Reaction equation

HRID 1370111 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:9][C:10]1[C:15]([NH2:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>C(#N)C>[C:1]([O:4][CH2:5][C:6]([N:9]1[C:10]2=[N:11][CH:12]=[C:13]([C:17]([F:18])([F:20])[F:19])[CH:14]=[C:15]2[NH:16][C:21]1=[O:22])([CH3:8])[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18509721HCID 18509721, compound

Product 1

HCID 18509897HCID 18509897, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2-acetoxy-1,1-dimethylethylamino)-3-amino-5-(trifluoromethyl)pyridine (1.5 g) in acetonitrile (15 mL) was added 1,1′-carbonyldiimidazole (1.25 g), and the mixture was stirred at 50° C. under nitrogen atmosphere for 2 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The separated organic layer was washed successively with 1 N-hydrochloric acid, water, an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and methanol (20:1). The obtained substance was triturated with diethyl ether to give 3-(2-acetoxy-1,1-dimethylethyl)-6-trifluoromethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (736.5 mg) as a pale brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe separated organic layer was washed successively with 1 N-hydrochloric acid, water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. washeluting with a mixture of chloroform and methanol (20:1)
  8. customThe obtained substance was triturated with diethyl ether

Sources & evidence

ORD record
ord-493e3d43723547d3bdfc9a87f46204b3
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

Loading…