Cesium carbonate → 1-[(4-chlorophenoxy)methyl]-N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068030ノート

反応式

HRID 1068030 の反応式
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:17]=3)[N:12]([CH2:37][O:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 88801alpha,4-DichloroanisoleHCID 178522870HCID 178522870、化合物

生成物 1

HCID 160739101-[(4-chlorophenoxy)methyl]-N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A suspension of N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 and cesium carbonate (0.33 gm) in DMF (2 mL) is treated with α,4-dichloroanisole (0.13 gm). The mixture is tightly capped and heated to 100° C. for 3 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane (50 mL) and washed with water. The aqueous phase is extracted with two additional portions of dichloromethane. The combined organic phase is washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 1% to 4% methanol in dichloromethane and then by recrystallization with acetonitrile to afford 0.20 gm of the title compound as a white solid.

後処理

  1. customfrom Preparation No
  2. customThe mixture is tightly capped
  3. temperatureto cool to room temperature
  4. washwashed with water
  5. extractionThe aqueous phase is extracted with two additional portions of dichloromethane
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by flash column chromatography
  10. washeluting with 1% to 4% methanol in dichloromethane
  11. customby recrystallization with acetonitrile

出典と根拠

ORDレコード
ord-511938b5b9b3472f8a84f21e0a579442
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

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