Water → [8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methyl Acetate

HRID 1166160Notes

Reaction equation

HRID 1166160 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.C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31].O>C(Cl)Cl>[C:30]([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])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 98826348-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 9819178[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methyl AcetateYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.3 g, 1.0 mmol) and triethylamine (0.014 ml, 1.0 mmol) in methylene chloride (10 ml) was added dropwise acetyl chloride (0.071 ml, 1.0 mmol). The reaction mixture was stirred for 1.5 h. at room temperature. Water was added and the organic layer was separated, washed with sodium bicarbonate solution, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using diethyl ether as eluent. Recrystallization from diethyl ether gave 0.16 g (47%) of the desired product.

Workup

  1. customthe organic layer was separated
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-d3055efe24694380abdabcdb1c3bcbdf
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

Loading…