Water → HCID 22672634, compound

HRID 1006668Notes

Reaction equation

HRID 1006668 reaction equation
[CH3:1][C:2]1[C:22](C)=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH:16](O)[CH3:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:24])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH:16]=[CH2:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 22672562HCID 22672562, compound

Product 1

HCID 22672634HCID 22672634, compoundYield 141.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-[8-(2,3-dimethylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-yl]-1-ethanol (0.2 g, 0.65 mmol) and p-toluenesulfonic acid (0.029 g, 0.15 mmol) in benzene (40 ml) was refluxed for 20 h with Dean-Stark water separation. The solvent was evaporated under reduced pressure, the residue was solved in methylene chloride and washed with saturated sodium bicarbonate solution. The organic layer was separated, dried and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:ethyl acetate (10:1) gave 0.062 g (33%) of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed with saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated under reduced pressure
  6. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-7724b8b864614de189511ea87b449fce
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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