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

HRID 11346ノート

反応式

HRID 11346 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6212Chloroform溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-43d8a7a728d449f7adb931a08b66fabf
出典データセット
uspto-grants-2006_08
特許番号
US07098221B2

反応ノート

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