Hydrochloric Acid → N-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide

HRID 2085290Notes

Reaction equation

HRID 2085290 reaction equation
[CH3:1][C:2]1[N:3]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[C:4]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=[C:6](OC3C=CC=CC=3)[C:5]=2[N:19]=1.C([O-])(=O)C.[NH4+:33].Cl>C(Cl)(Cl)Cl.CO.C(OCC)C>[NH2:33][C:6]1[C:5]2[N:19]=[C:2]([CH3:1])[N:3]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[C:4]=2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 12109129N-[4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide

Product 1

HCID 10125773N-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamideYield 59.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

N-[4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide (4.20 g, 10.4 mmol) and ammonium acetate (42 g) were combined and then heated in a sealed tube at 150° C. for 36 hrs. The reaction mixture was allowed to cool and then it was dissolved in chloroform. The solution was extracted with 10% aqueous sodium hydroxide solution. The aqueous layer was separated and then extracted multiple times with chloroform. The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellow oil. The oil was dissolved in methanol and combined with 1M hydrochloric acid in diethyl ether (10.4 mL). The resulting white precipitate was isolated by filtration and dried. The solid was dissolved in water and the solution was adjusted to pH 10 with solid sodium carbonate. The resulting white precipitate was isolated by filtration, washed with diethyl ether and then dried in a vacuum oven at 80° C. to provide 2.00 g of N-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide, m.p. 228-230° C.

Workup

  1. temperatureto cool
  2. extractionThe solution was extracted with 10% aqueous sodium hydroxide solution
  3. customThe aqueous layer was separated
  4. extractionextracted multiple times with chloroform
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide a yellow oil
  8. customThe resulting white precipitate was isolated by filtration
  9. customdried
  10. dissolutionThe solid was dissolved in water
  11. customThe resulting white precipitate was isolated by filtration
  12. washwashed with diethyl ether
  13. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-fffbc330752c49b58ae765ef490df49a
Source dataset
uspto-grants-2004_04
Patent number
US06720334B2

Reaction notes

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