Sodium Methoxide → HCID 15684565, compound

HRID 728154Notes

Reaction equation

HRID 728154 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH2:21]Cl)[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:25][O-:26].[Na+]>CO>[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([CH2:21][O:26][CH3:25])[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15684612HCID 15684612, compound

Product 1

HCID 15684565HCID 15684565, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-amino-6-[2-(7-chloromethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.4 g), and sodium methoxide (0.13 g) in methanol (10 ml) was stirred for 3 hours at 40°-50° C. and the solvent was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and tetrahydrofuran and the mixture was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by silica gel column chromatography eluting with a solution of chloroform and methanol (9:V/V). The fraction containing object compound were concentrated to give 2-amino-6-[2-(7-methoxymethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.22 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  3. washthe mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas purified by silica gel column chromatography
  8. washeluting with a solution of chloroform and methanol (9:V/V)
  9. additionThe fraction containing object compound
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-18880317a515422a9a556e3951889429
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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