Triethyl orthoacetate → 1-[2,6,7-Trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]eth-2-yl Acetate

HRID 1352547ノート

反応式

HRID 1352547 の反応式
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[NH2:23])(=[O:3])[CH3:2].[C:24](OCC)(OCC)(OCC)[CH3:25]>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:8]2[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:9]=2[N:23]=[C:24]1[CH3:25])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 66221Triethyl orthoacetateHCID 691934021-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl Acetate

生成物 1

HCID 219131671-[2,6,7-Trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]eth-2-yl Acetate収率 98.2%

試薬・触媒・溶媒 2

HCID 10176127Pyridinium chloride触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

1-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl acetate (10.5 g, 33.29 mmol), toluene (100 mL), pyridine hydrochloride (0.077 g, 0.6659 mmol), and triethyl orthoacetate (9.1 mL, 49.94 mmol) were combined with stirring and the resulting mixture was heated to a gentle reflux (about 95° C.) for 1.5 hours. The reaction was complete. The resulting reaction mixture was concentrated under reduced pressure to white solids, which were dissolved in ethyl acetate. The ethyl acetate solution was washed with water (3×) and brine (2×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was triturated with diethyl ether, filtered off, and dried at 60° C. overnight to provide 11.1 g of pure product, which was carried on to the next step.

後処理

  1. temperaturethe resulting mixture was heated to
  2. customThe resulting reaction mixture
  3. concentrationwas concentrated under reduced pressure to white solids, which
  4. dissolutionwere dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water (3×) and brine (2×)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was triturated with diethyl ether
  10. filtrationfiltered off
  11. customdried at 60° C. overnight

出典と根拠

ORDレコード
ord-9315a2c95ad8484f9544c873e6d3e440
出典データセット
uspto-grants-2007_05
特許番号
US07220758B2

反応ノート

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