Methanesulfonic anhydride → HCID 12109141, compound

HRID 1815012Notes

Reaction equation

HRID 1815012 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 1 N 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 1 N sodium hydroxide (10 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f7aebde80dd4a47a5d64cf5dbb81e5d
Source dataset
uspto-grants-2005_04
Patent number
US06878719B2

Reaction notes

Loading…