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Triethyl orthoacetate → 2,6,7-trimethyl-4-phenoxy-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridine

HRID 1352556
ノート
印刷プレビュー

反応式

HRID 1352556 の反応式
[CH3:1][C:2]1[C:3]([NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[C:4]([NH2:16])[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][C:7]=1[CH3:8].Cl.N1C=CC=[CH:33][CH:32]=1.C(OCC)(OCC)(OCC)C>C1(C)C=CC=CC=1>[CH3:32][C:33]1[N:17]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:3]2[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=[C:5]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[N:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 66221Triethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 691854145,6-dimethyl-2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridine-3,4-diamine

生成物 1

HCID 219131992,6,7-trimethyl-4-phenoxy-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
99 °C

実験手順

A solution of 5,6-dimethyl-2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridine-3,4-diamine (12 g) in toluene (300 ml) from Part C was combined with pyridine HCl (0.08 g) and triethyl orthoacetate (8.4 ml). Under a nitrogen atmosphere, the reaction mixture was heated to reflux (99° C.) for 1.5 hours. TLC and HPLC analysis indicated that the reaction was complete. The solvent was removed under reduced pressure. The resulting yellow oil was dissolved in dichloromethane and washed once with saturated potassium carbonate, 3 times with water, and 3 times with brine. The combined organic layers were dried with magnesium sulfate and concentrated under reduced pressure. The resulting yellow oil darkened slightly after being dried under vacuum at 70° C. overnight. The product was purified by column chromatography over silica using 95/5 ethyl acetate/methanol as the eluant. The product was dried and then triturated with diethyl ether to yield a white solid that was dried under vacuum at 80° C. overnight. NMR analysis of the dried solid indicated a pure product.

後処理

  1. temperatureUnder a nitrogen atmosphere, the reaction mixture was heated
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe resulting yellow oil was dissolved in dichloromethane
  4. washwashed once with saturated potassium carbonate, 3 times with water, and 3 times with brine
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customafter being dried under vacuum at 70° C. overnight
  8. customThe product was purified by column chromatography over silica using 95/5 ethyl acetate/methanol as the eluant
  9. customThe product was dried
  10. customtriturated with diethyl ether
  11. customto yield a white solid
  12. customthat was dried under vacuum at 80° C. overnight

出典と根拠

ORDレコード
ord-b5c5ebd5002b4198af1472884ffb9fcd
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07220758B2

反応ノート

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