HCID 53374913, compound → HCID 56587816, compound

HRID 1405999Notes

Reaction equation

HRID 1405999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[O:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[O:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 53374913HCID 53374913, compound

Product 1

HCID 56587816HCID 56587816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To obtain the HCl salt of the parent compound, the yellow solid was added to DCM: NaHCO3 (sat'd aqueous) (1:1) and the organic layer was separated, dried (MgSO4), filtered and concentrated. Afterwards, the title compound was dissolved in DCM (20 mL) and at 0° C. 4 M HCl in 1,4-dioxane (1 mL) was added. After 10 min, the ice bath was removed. A precipate formed after 30 min. The solvent was removed under reduced pressure to afford N-(3-chlorophenyl)isoxazolo[4,5-b]pyridin-3-amine HCl salt.

Workup

  1. customNaHCO3 (sat'd aqueous) (1:1) and the organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionAfterwards, the title compound was dissolved in DCM (20 mL) and at 0° C
  6. addition4 M HCl in 1,4-dioxane (1 mL) was added
  7. customthe ice bath was removed
  8. customA precipate formed after 30 min
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7c42f50ee7a24ed3a4a95d44449c42fa
Source dataset
uspto-grants-2014_12
Patent number
US08916584B2

Reaction notes

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