Hydrochloric Acid → HCID 76071675, compound

HRID 927043Notes

Reaction equation

HRID 927043 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][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:15][N:14]=2)=[N:10][O:11][CH:12]=1)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[C:8]([NH2:7])=[CH:12][O:11][N:10]=2)=[N:14][CH:15]=1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90203155HCID 90203155, compound

Product 1

HCID 76071675HCID 76071675, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[3-(5-Phenethyloxy-pyridin-2-yl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (60 mg, 0.158 mmol) was dissolved in dioxane (9 mL) and treated with conc. HCl (1.8 mL). After stirring for 14 h, the reaction mixture combined with satd aqueous NaHCO3 (10 mL). The organic layer was separated and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave a beige solid from which 3-(5-phenethyloxy-pyridin-2-yl)-isoxazol-4-ylamine (9.8 mg, 22%) was isolated by chromatography (30% ethyl acetate in hexane). HRMS: 281.1285 (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-206c2ed707f7419da61fd7d51c30b8d8
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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