Dichloromethane → HCID 22672630, compound

HRID 1369572Notes

Reaction equation

HRID 1369572 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[K+].[Cl:24][C:25]([O:27][CH3:28])=[O:26].C(Cl)Cl>CC(C)=O>[ClH:24].[C:25](=[O:26])([O:27][CH3:28])[O:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 22672646HCID 22672646, compound

Product 1

HCID 22672630HCID 22672630, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-(2-hydroxy-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.068 g, 0.24 mmol) sodium carbonate (0.12 g, 1.1 mmol), and potassium hydroxide (0.019 g, 0.34 mmol) in acetone (12 ml) was stirred for 15 min in room temperature in a nitrogen atmosphere. Methyl chloroformate (0.023 g, 0.24 mmol) was added and the reaction mixture was stirred for 70 min. Methylene chloride was added and the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in methylene chloride, washed with saturated sodium bicarbonate and water and the organic layer was separated, dried and evaporated under reduced pressure. The residue was purified by by column chromatography on silica gel using methylene chloride:methanol (100:5) as eluent and treated with HCl/diethyl ether to give 0.025 g (28%) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred for 70 min
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with saturated sodium bicarbonate and water
  6. customthe organic layer was separated
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe residue was purified by by column chromatography on silica gel
  10. additiontreated with HCl/diethyl ether

Sources & evidence

ORD record
ord-3c1224e884bf43a2b8e3e86cc86efcd3
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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