Hydrochloric Acid → 6-(Cyclohexylamino)-5-nitropyridin-2-yl methanesulfonate

HRID 1890355Notes

Reaction equation

HRID 1890355 reaction equation
[CH:1]1([NH:7][C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH3:18][S:19]([O:14][C:12]1[CH:11]=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[C:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:13]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178526704HCID 178526704, compound

Product 1

HCID 866552596-(Cyclohexylamino)-5-nitropyridin-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(Cyclohexylamino)-5-nitropyridin-2-ol (1.35 g, 5.69 mmol) was dissolved in DCM (1150 mL). Methanesulfonyl chloride (0.782 g, 6.83 mmol) and triethylamine (1.152 g, 11.38 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, acidified with 1 M HCl and extracted with DCM. The organic layers were combined, washed with water, dried over Na2SO4, and concentrated under reduced pressure to give the title compound without further purification. LCMS m/z=316.30 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-035812f4266345429d9b39c9769f835d
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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