1,4-Dioxane → HCID 15953524, compound

HRID 1696252Notes

Reaction equation

HRID 1696252 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[NH:10][C:9]1=[O:20].O1CCOCC1.C(=O)([O-])O.[Na+].[CH3:32][N:33]([CH3:38])[S:34](Cl)(=[O:36])=[O:35]>C(Cl)(Cl)Cl>[CH3:32][N:33]([CH3:38])[S:34]([N:5]1[CH2:6][CH2:7][C@@H:2]([CH3:1])[C@@H:3]([N:8]2[C:12]3=[C:13]4[CH:19]=[CH:18][NH:17][C:14]4=[N:15][CH:16]=[C:11]3[NH:10][C:9]2=[O:20])[CH2:4]1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium BicarbonateHCID 67277969HCID 67277969, compound

Product 1

HCID 15953524HCID 15953524, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of rel-1-[(3R,4R)-4-methylpiperidin-3-yl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (80 mg), dioxane (1.6 mL) and 4M saturated aqueous sodium hydrogencarbonate (2.4 mL) was added dimethylsulfamoyl chloride (51 mg) at ambient temperature. The mixture was stirred for 2 hours then chloroform (8 mL) was added. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography to give rel-(3R,4R)—N,N,4-trimethyl-3-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)piperidine-1-sulfonamide (41 mg) as a colorless solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5d104e948014c3e8b4587cab6f80670
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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