HCID 15171562, compound → HCID 15684567, compound

HRID 728156Notes

Reaction equation

HRID 728156 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][N:22]=[N+]=[N-])[CH:18]=[CH:17][N:16]4[C:25]=3[CH3:26])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H][H]>[Pd].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][NH2:22])[CH:18]=[CH:17][N:16]4[C:25]=3[CH3:26])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 15171562HCID 15171562, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15684567HCID 15684567, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.3 g) was added to a solution of 2-amino-6-[2-(7-azidomethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (1.0 g) in methanol (100 ml) and the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure of hydrogen gas. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by alumina column chromatography eluting with a solution of chloroform and methanol (4:1, V/V). The fractions containing object compound was evaporated to give 2-amino-6-[2-(7-aminomethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.41 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by alumina column chromatography
  4. washeluting with a solution of chloroform and methanol (4:1, V/V)
  5. additionThe fractions containing object compound
  6. customwas evaporated

Sources & evidence

ORD record
ord-5202b61a45ff4f8f8e108c6343eb44eb
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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