Water → HCID 15171562, compound

HRID 728155Notes

Reaction equation

HRID 728155 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.[N-:25]=[N+:26]=[N-:27].[Na+].[N-]=[N+]=[N-].[K+].O>CN(C)C=O>[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:25]=[N+:26]=[N-:27])[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 10290740Potassium azideHCID 15684612HCID 15684612, compound

Product 1

HCID 15171562HCID 15171562, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-[2-(7-chloromethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (1.3 g), sodium azide (0.5 g) and potassium azide (1.3 g) in N,N-dimethylformamide (26 ml) was stirred for 17 hours at ambient temperature and the mixture was poured into water. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated with diethyl ether to give 2-amino-6-[2-(7-azidomethyl-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (1.21 g).

Workup

  1. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-01f405e2eea44c4daa8f123999a5dda6
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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