Hydrochloric Acid → HCID 76071679, compound

HRID 927052Notes

Reaction equation

HRID 927052 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:9]3[C:8]([NH2:7])=[CH:12][O:11][N:10]=3)=[CH:14][CH:15]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90203859HCID 90203859, compound

Product 1

HCID 76071679HCID 76071679, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{3-[4-(Pyridin-3-ylmethoxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (from previous reaction) was dissolved in dioxane (18 mL) and treated with conc. HCl (3.6 mL). After stirring for 3 h, the reaction mixture combined with satd aqueous NaHCO3 (20 mL). The organic layer was separated and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave an oily white solid from which 3-[4-(pyridin-3-ylmethoxy)-phenyl]-isoxazol-4-ylamine (6.5 mg, 6.7%) was isolated as a white solid by chromatography (5% CH3OH in CH2Cl2). HRMS: 268.108 (M+1)

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration
  4. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-0df94fea2c174a85b6827be8d9654ccf
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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