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

HRID 1068011
ノート
印刷プレビュー

反応式

HRID 1068011 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+].[C:36]1([S:42][CH2:43]Cl)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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]([CH2:43][S:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=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 3

HCID 10796Cesium carbonateHCID 81623Chloromethyl phenyl sulphideHCID 178522870HCID 178522870、化合物

生成物 1

HCID 9915062N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-1-(phenylsulfanylmethyl)quinoline-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
75 °C

実験手順

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 in DMF (4 mL) is treated with cesium carbonate (0.30 gm) and chloromethyl phenyl sulfide (0.08 mL). The mixture is tightly capped and heated to 75° C. for 8 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane (50 mL) and washed with water (2×10 mL), brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 2% to 4% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.19 gm of the title compound as a white solid.

後処理

  1. customThe mixture is tightly capped
  2. temperatureto cool to room temperature
  3. washwashed with water (2×10 mL), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by flash column chromatography
  7. washeluting with 2% to 4% methanol in dichloromethane
  8. customby recrystallization from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-8fe13cde981548eaaf7502beadeadcee
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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