Methanesulfonyl chloride → HCID 59464028, compound

HRID 1713813Notes

Reaction equation

HRID 1713813 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[N:11][CH:12]=1)=[O:5].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>Cl.O1CCOCC1.O>[CH3:27][S:28]([N:16]1[CH2:17][CH2:18][N:13]([C:10]2[N:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]([O:2][CH3:1])=[O:26])=[CH:8][CH:9]=2)[CH2:14][CH2:15]1)(=[O:30])=[O:29]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68684444HCID 68684444, compound2×

Product 1

HCID 59464028HCID 59464028, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl 4-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)piperazine-1-carboxylate (Intermediate 16, 4 g, 11 mmol) in 4N HCl/dioxan (25 mL) was stood for 16 h then concentrated by evaporation. The residue was dissolved in a mixture of DMF (20 mL) and pyridine (7 mL) then methanesulphonyl chloride (1.28 mL, 16.48 mmol) was added. The mixture was stirred for 3 hours then was diluted with water (50 mL) and extracted with dichloromethane (2×100 mL). The organic extracts were dried and concentrated by evaporation to give the title compound as a solid that was used without further purification; MS m/e MH+ 343.

Workup

  1. concentrationthen concentrated by evaporation
  2. dissolutionThe residue was dissolved in a mixture of DMF (20 mL) and pyridine (7 mL)
  3. extractionextracted with dichloromethane (2×100 mL)
  4. customThe organic extracts were dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-01441601eefc4a7e875bfb9b5d365ef4
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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