Ethyl Acetate → HCID 66747915, compound

HRID 1622783Notes

Reaction equation

HRID 1622783 reaction equation
[O:1]=[S:2]1(=[O:19])[CH2:7][CH2:6][N:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:4]2=[N:3]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:27][CH:28]([CH3:30])[CH3:29].CCOC(C)=O>CS(C)=O.C1COCC1>[CH3:27][CH:28]([CH3:30])[CH2:29][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:4]3=[N:3][S:2](=[O:1])(=[O:19])[CH2:7][CH2:6][N:5]3[CH:8]=[CH:9][CH:10]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10556Isobutyl iodide2×HCID 11430Potassium CarbonateHCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66747915HCID 66747915, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (200 mg), potassium carbonate (260 mg) in DMSO (4 mL) was added 1-iodo-2-methylpropane (173 mg). The mixture was stirred at 130° C. for 1 hr. Another 1-iodo-2-methylpropane (0.10 mL) was added and the mixture was stirred at room temperature overnight. 0.5N NaOHaq, EtOAc and THF were added and the extracted organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from THF-MeOH/IPE to give the title compound (104 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe extracted organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from THF-MeOH/IPE

Sources & evidence

ORD record
ord-c49adf94ee5942cf80501194eeb7b6b4
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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