Ethyl Acetate → HCID 66747915, compound

HRID 1405850Notes

Reaction equation

HRID 1405850 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-8effe1c48a5e439eb0939d716bc50957
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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