3-Mesyloxy-5-hexyn-2-one → HCID 14499825, compound

HRID 2073804Notes

Reaction equation

HRID 2073804 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[C:15]([NH:16][C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:21])=[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>CO.C(Cl)(Cl)Cl>[CH3:21][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][C:17]([O:19][CH3:20])=[O:18])[C:10]=1[CH2:9][NH: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

Participants

5

Reactant 2

HCID 143683463-Mesyloxy-5-hexyn-2-oneHCID 144998172-Amino-3-(2-methyl-6-methoxycarbonylaminobenzylamino)pyridine

Product 1

HCID 14499825HCID 14499825, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

A mixture of 2-amino-3-(2-methyl-6-methoxycarbonylaminobenzylamino)pyridine (180 mg) and 3-mesyloxy-5-hexyn-2-one (120 mg) in methanol (0.36 ml) and chloroform (0.36 ml) was refluxed for 20 hours. After cooling, chloroform was added to the mixture and the resultant mixture was washed with an aqueous solution of sodium carbonate and water. The solvent was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (4 g), eluting with chloroform to give an oily product. The residue was triturated with diethyl ether to give 8-(2-methyl-6-methoxycarbonylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (127 mg).

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureAfter cooling
  3. washthe resultant mixture was washed with an aqueous solution of sodium carbonate and water
  4. customThe solvent was evaporated under reduced pressure
  5. washeluting with chloroform
  6. customto give an oily product
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c9928290769441f3b78c69e14e40ee76
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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