3-Mesyloxy-5-hexyn-2-one → Methyl hydrogen [3-methyl-2-({[2-methyl-3-(prop-2-yn-1-yl)imidazo[1,2-a]pyridin-8-yl]oxy}methyl)phenyl]carbonimidate

HRID 1762210Notes

Reaction equation

HRID 1762210 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[NH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:27]([CH2:31][C:32]#[CH:33])[C:28](=O)[CH3:29])(C)(=O)=O>C(O)C>[CH3:21][O:20][C:18]([NH:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=1[CH2:9][O:8][C:7]1[C:2]2[N:3]([C:27]([CH2:31][C:32]#[CH:33])=[C:28]([CH3:29])[N:1]=2)[CH:4]=[CH:5][CH:6]=1)=[O:19]

Participants

4

Reactant 2

HCID 143683463-Mesyloxy-5-hexyn-2-oneHCID 20042533HCID 20042533, compound

Product 1

HCID 195217Methyl hydrogen [3-methyl-2-({[2-methyl-3-(prop-2-yn-1-yl)imidazo[1,2-a]pyridin-8-yl]oxy}methyl)phenyl]carbonimidate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2-methoxycarbonylamino-6-methylbenzyloxy)pyridine (4.22 g) and 3-mesyloxy-5-hexyn-2-one (2.74 g) in ethanol (42 ml) was refluxed for 62 hours and then evaporated in vacuo. To the residue was added and aqueous solution of sodium bicarbonate and the insoluble material was collected by filtration. The crude product was purified by column chromatography on silica gel (150 g) with methylene chloride and then a mixture of methylene chloride and acetonitrile (10:1) as eluents to afford a solid, which was recrystallized from a mixture of ethyl acetate and cyclohexane to give 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine.

Workup

  1. temperaturewas refluxed for 62 hours
  2. customevaporated in vacuo
  3. additionTo the residue was added
  4. filtrationaqueous solution of sodium bicarbonate and the insoluble material was collected by filtration
  5. customThe crude product was purified by column chromatography on silica gel (150 g) with methylene chloride
  6. additiona mixture of methylene chloride and acetonitrile (10:1) as eluents
  7. customto afford a solid, which
  8. customwas recrystallized from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-f25b130cccef4d769382420f03d39448
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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