Hydrochloric Acid → HCID 15684561, compound

HRID 728157Notes

Reaction equation

HRID 728157 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]([O:21][CH3:22])[CH:18]=[CH:17][N:16]4[CH:23]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:24]N1C(=O)CCC1=O.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[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]([O:21][CH3:22])[CH:18]=[CH:17][N:16]4[C:23]=3[Cl:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 15684559HCID 15684559, compound

Product 1

HCID 15684561HCID 15684561, compoundYield 37.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-6-[2-(7-methoxyimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (1.0 g) and N-chlorosuccinimide (0.43 g) in dioxane (15 ml) was stirred for 2 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 1 with 6N hydrochloric acid. The separated aqueous layer was adjusted to pH 8 with 20% potassium carbonate aqueous solution and the mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine 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 (19:1, V/V). The fractions containing object compound were concentrated to give 2-amino-6-[2-(3-chloro-7-methoxyimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.41 g).

Workup

  1. additionTo the reaction mixture was added
  2. extractionthe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  3. washThe extract was washed with brine
  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 (19:1, V/V)
  9. additionThe fractions containing object compound
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-c6de9ec170a6443db31dfadde9244b1c
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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