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Dichloromethane → N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068031
ノート
印刷プレビュー

反応式

HRID 1068031 の反応式
ClC1C=CC(C[C:7]2[C:16]([C:17]([NH2:19])=[O:18])=[C:15]([OH:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:13]=3)[N:8]=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:36][O:37][CH2:38][CH2:39][O:40][CH2:41]Cl.Cl[CH2:44][Cl:45]>CN(C=O)C>[Cl:45][C:44]1[CH:14]=[CH:13][C:12]([CH2:21][NH:19][C:17]([C:16]2[C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:13]=3)[N:8]([CH2:41][O:40][CH2:39][CH2:38][O:37][CH3:36])[CH:7]=2)=[O:18])=[CH:11][CH:10]=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

6

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 178513551HCID 178513551、化合物

生成物 1

HCID 16073911N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
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 (0.34 gm) in DMF (2 mL) is treated with 2-methoxyethoxymethyl chloride (0.07 mL). 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 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 5% methanol in dichloromethane and then by recrystallization with acetonitrile to afford 0.08 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 5% methanol in dichloromethane
  11. customby recrystallization with acetonitrile

出典と根拠

ORDレコード
ord-1f30f98ef84040279c17b872b2a3f157
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06248739B1

反応ノート

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