Ethyl chloroformate → [8-(2,6-Dimethylbenzylamino)-3-meihylimidazo[1,2-a]pyridin-2-yl]methyl Ethyl Carbonate

HRID 1166161Notes

Reaction equation

HRID 1166161 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15][OH:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:24](=[O:25])([O:26][CH2:27][CH3:28])[O:16][CH2:15][C:13]1[N:14]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:2]=3[CH3:1])=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformate2×HCID 516892Sodium BicarbonateHCID 98826348-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 9951111[8-(2,6-Dimethylbenzylamino)-3-meihylimidazo[1,2-a]pyridin-2-yl]methyl Ethyl CarbonateYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.4 g, 1.3 mmol) and ethyl chloroformate (0.13 ml, 1.3 mmol) were solved in methylene chloride (20 ml) and were refluxed for 3 h. An additional amount of ethyl chloroformate (0.13 ml, 1.3 mmol) was added and the reaction mixture was refuxed 20 h. A sodium bicarbonate solution was added, the organic layer was separated dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using diethyl ether as eluent and crystallization from diethyl ether: petroleum ether (1:2) gave 0.11 g (23%) of the title compound.

Workup

  1. temperaturewere refluxed for 3 h
  2. customthe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel
  6. customcrystallization from diethyl ether: petroleum ether (1:2)

Sources & evidence

ORD record
ord-b69ddcc63d924d7ca3c03bce3d45ce3b
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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