Triethylamine → Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate

HRID 72430

Reaction equation

HRID 72430 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:13][CH:14]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:15]2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67958303Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

Product 1

HCID 86697874Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinateYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate (D62) (50 mg, 0.206 mmol) and triethylamine (0.057 ml, 0.412 mmol) in dimethylformamide (0.26 ml) cooled at 0° C., methansulfonyl chloride (0.016 ml, 0.206 mmole) was added dropwise and the reaction mixture stirred at the same temperature for 1 h. After solvent evaporation the obtained residue was purified by SPE-Si (5 g) eluting with a mixture petroleum ether/ethyl acetate from 90/10 to 70/30. Collected fractions, after solvent evaporation, afforded the title compound (D63) (53 mg)

Workup

  1. customAfter solvent evaporation the obtained residue
  2. customwas purified by SPE-Si (5 g)
  3. washeluting with a mixture petroleum ether/ethyl acetate from 90/10 to 70/30
  4. customCollected fractions, after solvent evaporation

Sources & evidence

ORD record
ord-014c4490700b4569a0298cb9b75a7719
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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