Methanesulfonyl chloride → HCID 84332484, compound

HRID 1486819Notes

Reaction equation

HRID 1486819 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11]C)=[O:9])=[CH:4][CH:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([NH:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 235927Ethyl 6-Aminonicotinate

Product 1

HCID 84332484HCID 84332484, compoundYield 131.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-aminopyridine-3-carboxylate (738 mg, 4.44 mmol) was dissolved in pyridine (20 mL), cooled to 0° C. and methanesulfonyl chloride (1.72 mL, 22.2 mmol) was added. The reaction mixture was stirred at room temperature for 16 h, concentrated in vacuo and partitioned between DCM (50 mL) and 1M aq citric acid (50 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo to give the crude title compound (1.34 g) as a brown solid. LCMS (ES+): 245.1 [MH]+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between DCM (50 mL) and 1M aq citric acid (50 mL)
  3. dry with materialThe organic fraction was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-354fae2768814dde9cc5eefebae2d801
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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