Potassium Carbonate → HCID 66823786, compound

HRID 1405710Notes

Reaction equation

HRID 1405710 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[O:13]=[S:14]1(=[O:31])[CH2:19][CH2:18][N:17]2[CH:20]=[CH:21][CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C:16]2=[N:15]1.[OH-].[Na+]>CS(C)=O>[CH:8]1([O:30][C:27]2[CH:26]=[CH:25][C:24]([C:23]3[C:16]4=[N:15][S:14](=[O:31])(=[O:13])[CH2:19][CH2:18][N:17]4[CH:20]=[CH:21][CH:22]=3)=[CH:29][CH:28]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 73784Iodocyclopentane2×HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66823786HCID 66823786, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of potassium carbonate (450 mg), iodocyclopentane (639 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (3 mL) was stirred at 130° C. overnight. Then iodocyclopentane (639 mg) was added and the mixture was stirred at 150° C. for 5 hr. The mixture was poured into 1N NaOH aq. and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give crude product (81.1 mg). The crude product was purified by preparative HPLC (C18, eluted with H2O in acetonitrile containing 0.1% TFA). The desired fraction was neutralized with sat.NaHCO3 aq. and extracted with EtOAc. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (52.3 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at 150° C. for 5 hr
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with 1N NaOH aq. and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  8. customto give crude product (81.1 mg)
  9. customThe crude product was purified by preparative HPLC (C18, eluted with H2O in acetonitrile containing 0.1% TFA)
  10. extractionNaHCO3 aq. and extracted with EtOAc
  11. customThe organic layer was separated
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4437d9eed7cc433583785b22ebb0544d
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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