3-Isoxazolamine, 5-(1,1-dimethylethyl)- → HCID 59674136, compound

HRID 1391545Notes

Reaction equation

HRID 1391545 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[N:3]=1.[C:15]([C:19]1[O:23][N:22]=[C:21]([NH2:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>C(O)(C)C.Cl>[C:15]([C:19]1[O:23][N:22]=[C:21]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=3[N:3]=2)[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 108223912-Chloro-1-methyl-5-nitro-1H-benzimidazole

Product 1

HCID 59674136HCID 59674136, compoundYield 317.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-Chloro-1-methyl-5-nitro-1H-benzoimidazole (200 mg, 0.19 mmol) and 5-tert-Butyl-isoxazol-3-ylamine (265 mg, 1.90 mmol) in isopropanol (15 ml) was added a solution of HCl (3 drops, 4.0 m in dioxane). The reaction was heated to 80° C. and after 20 h. the reaction mixture was cooled to rt. The solvent was evaporated to dryness and the resultant solid was dissolved in EtOAc and neutralized by a 10% NaHCO3 water solution. The combined organic layers were washed with water, dried over MgSO4 and concentrated to give a foam. The crude material was purified through silica gel to give the title compound as a yellow solid (190 mg, 63%). MS (ESI) m/z=316 [M+H].

Workup

  1. temperaturewas cooled to rt
  2. customThe solvent was evaporated to dryness
  3. dissolutionthe resultant solid was dissolved in EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a foam
  8. customThe crude material was purified through silica gel

Sources & evidence

ORD record
ord-8b8b14432ed848cb861e07e5ab948fca
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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