Ethyl chloroformate → [6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-carbamic acid ethyl ester

HRID 548836Notes

Reaction equation

HRID 548836 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:20]=[N:19][C:18]([NH2:21])=[CH:17][CH:16]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:26]([O:25][C:23](=[O:24])[NH:21][C:18]1[N:19]=[N:20][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1)[CH3:27]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 426297716-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine

Product 1

HCID 42630374[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-carbamic acid ethyl esterYield 73.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine (280 mg, 1 mmol) and p-N,N-dimethylaminopyridine (61 mg, 0.5 mmol) in pyridine (5 mL) was added ethyl chloroformate (0.11 mL, 1.2 mmol) at room temperature. The resulting mixture was stirred at room temperature for 5 h. After evaporation the residue was extracted with ethyl acetate/water and the organic phase was dried over sodium sulfate and concentrated. Chromatography (SiO2, heptane/ethyl acetate=100:0 to 70:30) afforded the title compound (260 mg, 73%) as a white solid. MS: m/e=355.0 [M+H]+.

Workup

  1. customAfter evaporation the residue
  2. extractionwas extracted with ethyl acetate/water
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb0db15ef7574e92afdd4b31d6b55b4e
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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