Methanesulfonic anhydride → HCID 12109141, compound

HRID 1060675Notes

Reaction equation

HRID 1060675 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[CH2:10]([O:12][CH2:13][C:14]1[N:15]([CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])[C:16]2[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]=2[N:30]=1)[CH3:11]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:10]([O:12][CH2:13][C:14]1[N:15]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][S:2]([CH3:1])(=[O:5])=[O:3])[C:16]2[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]=2[N:30]=1)[CH3:11]

Participants

5

Reactant 2

HCID 81560Methanesulfonic anhydrideHCID 12109140HCID 12109140, compound

Product 1

HCID 12109141HCID 12109141, compoundYield 142.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Methane sulfonic anhydride (0.822 g, 4.72 mmol) was added over a period of 5 minutes to a solution of 4-[2-(ethoxymethyl)-6-methyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]butan-1-amine (1.5 g, 4.23 mmol) in a mixture of chloroform (35 mL) and triethylamine (0.77 mL). The reaction mixture was allowed to stir for 2.5 hours then it was washed with 1N sodium hydroxide (10 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 2.6 g of crude N-[4-(2-ethoxymethyl-6-methyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide.

Workup

  1. washit was washed with 1N sodium hydroxide (10 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c31bb185fe8d4c2ab19c642e3e82f86e
Source dataset
uspto-grants-2003_02
Patent number
US06525064B1

Reaction notes

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