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

HRID 1060700ノート

反応式

HRID 1060700 の反応式
[C:1]([O-:4])(=O)[CH3:2].[NH4+:5].[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](OC3C=CC=CC=3)[C:10]=2[N:24]=1.[ClH:35]>C(O)(C)C.C(OCC)C>[ClH:35].[NH2:5][C:11]1[C:10]2[N:24]=[C:7]([CH3:6])[N:8]([CH2:25][CH2:26][NH:27][C:1](=[O:4])[CH3:2])[C:9]=2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 21973834tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate

生成物 1

HCID 22499154N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]acetamide hydrochloride

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒

反応条件

温度
160 °C

実験手順

A mixture of ammonium acetate (95 g) and tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate (9.5 g) was heated at 160° C. in a sealed tube for 24 hours. The reaction mixture was allowed to cool to ambient temperature and then it was partitioned between water and chloroform. The aqueous layer was made basic (pH 13) with 50% sodium hydroxide and then extracted with chloroform (10×400 mL). The combined organics were dried over magnesium sulfate and then concentrated under reduced pressure to provide a brown solid. The solid was dissolved in warm isopropanol (80 mL) and then combined with 1M hydrochloric acid in diethyl ether (23.7 mL). The resulting precipitate was isolated by filtration, washed with cold isopropanol and diethyl ether, and then dried in a vacuum oven at 80° C. overnight to provide 5.0 g of N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]acetamide hydrochloride as a white solid, m.p. >250° C. Analysis: Calculated for: C13H19N5O·1.00 HCl: % C, 52.43; % H, 6.77; % N, 23.52; Found: % C, 52.25; % H, 6.81; % N, 23.41.

後処理

  1. temperatureto cool to ambient temperature
  2. customit was partitioned between water and chloroform
  3. extractionextracted with chloroform (10×400 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a brown solid
  7. customThe resulting precipitate was isolated by filtration
  8. washwashed with cold isopropanol and diethyl ether
  9. customdried in a vacuum oven at 80° C. overnight

出典と根拠

ORDレコード
ord-934e3e65d3284671b2881b21020a1e53
出典データセット
uspto-grants-2003_02
特許番号
US06525064B1

反応ノート

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