2-Amino-3-(2-methylbenzylamino)pyridine → 8-(2-Methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

HRID 4301

Reaction equation

HRID 4301 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:22]([CH2:26][C:27]#[CH:28])[C:23](=O)[CH3:24])(C)(=O)=O>C(O)C>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:7]1[C:2]2[N:3]([C:22]([CH2:26][C:27]#[CH:28])=[C:23]([CH3:24])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 138258912-Amino-3-(2-methylbenzylamino)pyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

Product 1

HCID 138259268-(2-Methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridineYield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-3-(2-methylbenzylamino)pyridine (2 g) and 3-mesyloxy-5-hexyn-2-one (1.78 g) in ethanol (40 ml) was refluxed for 31.5 hours and then evaporated in vacuo. The residue was treated with aqueous sodium bicarbonate solution and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (40 g) with a mixtutre of methylene chloride and ethyl acetate (50:1 to 10:1) as an eluent to give 8-(2-methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.82 g).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was treated with aqueous sodium bicarbonate solution
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (40 g) with a mixtutre of methylene chloride and ethyl acetate (50:1 to 10:1) as an eluent

Sources & evidence

ORD record
ord-02f0036534674dbdbf7bb937e43757ec
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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