2-Chloropyridine → HCID 66824096, compound

HRID 2036003Notes

Reaction equation

HRID 2036003 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[O:8]=[S:9]1(=[O:26])[CH2:14][CH2:13][N:12]2[CH:15]=[CH:16][CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:11]2=[N:10]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:11]3=[N:10][S:9](=[O:26])(=[O:8])[CH2:14][CH2:13][N:12]3[CH:15]=[CH:16][CH:17]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 11430Potassium CarbonateHCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 66824096HCID 66824096, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloropyridine (0.132 mL) was added to a solution of 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) and potassium carbonate (390 mg) in DMSO (6 mL). The mixture was stirred at 120° C. under nitrogen overnight. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and crystallized from THF-IPE to give the title compound (3.3 mg) as colorless crystals.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  8. customcrystallized from THF-IPE

Sources & evidence

ORD record
ord-2b7e895a3c5d41cebe65ac8b634f6ae3
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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