3-Bromo-2-oxo-N-phenylpropanamide → 6-(1-hydroxy-1-methylethyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645361ノート

反応式

HRID 645361 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:13][C:14](=O)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>COCCOC>[OH:11][C:8]([C:5]1[CH:4]=[CH:3][C:2]2[N:7]([CH:13]=[C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[N:1]=2)[CH:6]=1)([CH3:9])[CH3:10]

参加物

4

反応物 2

HCID 132915193-Bromo-2-oxo-N-phenylpropanamideHCID 594737712-(6-Aminopyridin-3-yl)propan-2-ol

生成物 1

HCID 686153916-(1-hydroxy-1-methylethyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide収率 32.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
25 °C

実験手順

A solution of 100 mg of 2-(6-aminopyridin-3-yl)propan-2-ol in 10 ml of 1,2-dimethoxyethane is treated with 190 mg of 3-bromo-2-oxo-N-phenylpropionamide, then stirred at 25° C. for 15 hours and brought to reflux for 3 hours. The reaction mixture is concentrated to dryness under reduced pressure and the residue is taken up in 40 ml of ethyl acetate and 40 ml of a saturated sodium carbonate solution. The aqueous phase is washed twice with 40 ml of ethyl acetate. The combined organic phases are dried and concentrated to dryness under reduced pressure. The residue is chromatographed on a cartridge of 40 g of silica, elution being carried out with dichloromethane and then with mixtures of dichloromethane and methanol, 97/3 and then 95/5. The fractions comprising the expected product are combined and concentrated to dryness to give 63 mg of 6-(1-hydroxy-1-methylethyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

後処理

  1. temperatureto reflux for 3 hours
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. washThe aqueous phase is washed twice with 40 ml of ethyl acetate
  4. customThe combined organic phases are dried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue is chromatographed on a cartridge of 40 g of silica, elution
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-fa5d2648213a4da7a5cd6c524d36a9ca
出典データセット
uspto-grants-2010_04
特許番号
US07704989B2

反応ノート

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