Methanol → HCID 66642984, compound

HRID 536721Notes

Reaction equation

HRID 536721 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.CN([CH:16]=[O:17])C>CCOC(C)=O>[C:1]([C:5]1[O:9][N:8]([CH2:2][C@H:1]2[CH2:5][CH2:6][CH2:16][O:17]2)[C:7](=[NH:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6228DimethylformamideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 66642984HCID 66642984, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-tert-butylisoxazol-3-amine (1 g, 7.1 mmol) and a solution of Example 39A (1.7 g, 6.8 mmol) in 1.5 mL DMF was warmed to 85° C. and was allowed to stir for 70 hours at 85° C. The mixture was cooled to ambient temperature, concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 50% hexanes in EtOAc then 10% CH3OH in EtOAc) to afford the title compound (0.48 g, 1.2 mmol, 17% yield). MS (DCI/NH3) m/z 225 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography (SiO2, 50% hexanes in EtOAc

Sources & evidence

ORD record
ord-c02857f25eb245179e4cbe455a262e78
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

Loading…