Sodium Iodide → HCID 66748003, compound

HRID 1622651Notes

Reaction equation

HRID 1622651 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH2:11][CH3:12])[CH2:9][CH3:10].[I-].[Na+].[O:15]=[S:16]1(=[O:33])[CH2:21][CH2:20][N:19]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:18]2=[N:17]1.[OH-].[Na+]>CS(C)=O>[CH2:9]([CH:8]([O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]2[C:18]3=[N:17][S:16](=[O:33])(=[O:15])[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=2)=[CH:31][CH:30]=1)[CH2:11][CH3:12])[CH3:10]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 157383-BromopentaneHCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66748003HCID 66748003, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of potassium carbonate (750 mg), 3-bromopentane (820 mg), sodium iodide (814 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (5 mL) was stirred at 150° C. for 3 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 a solid. This material 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 (36.1 mg) as a pale yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  7. customto give a solid
  8. customThis material was purified by preparative HPLC (C18, eluted with H2O in acetonitrile containing 0.1% TFA)
  9. extractionextracted with EtOAc
  10. customThe organic layer was separated
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf5f41aca2414eb384ed110e881731e0
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

Loading…