Pyridine → HCID 86731663, compound

HRID 1504770Notes

Reaction equation

HRID 1504770 reaction equation
N1C=CC=CC=1.[N:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[NH2:13][C:12]1[N:7]=[C:8]([NH:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 88612,6-DiaminopyridineHCID 31297Methanesulfonyl chloride

Product 1

HCID 86731663HCID 86731663, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (0.130 mL, 1.60 mmol) was added to pyridine-2,6-diamine (350 mg, 3.21 mmol) in DCM (6.4 mL). The reaction mixture was cooled to 0° C., and then methanesulfonyl chloride (0.124 mL, 1.60 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (30-100% acetone/hexanes, linear gradient) to afford N-(6-aminopyridin-2-yl)methanesulfonamide (˜50% purity) that was used without further purification. MS ESI calc'd. for C6H10N3O2S [M+H]+ 188. found 188.

Workup

  1. temperatureto warm to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (30-100% acetone/hexanes, linear gradient)

Sources & evidence

ORD record
ord-8ce1172889e44268aa429cc3f03368ba
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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