Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

HRID 1814878

反応式

HRID 1814878 の反応式
[CH3:1][NH:2][CH2:3][CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[OH:5].[Cl:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][NH:22][C:23]([C:25]2[C:26](=[O:37])[C:27]3[CH:34]=[C:33]([CH2:35]Cl)[O:32][C:28]=3[N:29]([CH3:31])[CH:30]=2)=[O:24])=[CH:19][CH:18]=1.O>CN(C=O)C>[Cl:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][NH:22][C:23]([C:25]2[C:26](=[O:37])[C:27]3[CH:34]=[C:33]([CH2:35][N:2]([CH2:3][CH:4]([OH:5])[C:6]4[CH:15]=[CH:14][C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[N:7]=4)[CH3:1])[O:32][C:28]=3[N:29]([CH3:31])[CH:30]=2)=[O:24])=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 962WaterHCID 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamideHCID 10149073Rac-2-(methylamino)-1-quinolin-2-ylethanol

生成物 1

HCID 10289493N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide収率 48.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

N,N-biisopropylethylamine (0.11 mL) and rac-2-(methylamino)-1-quinolin-2-ylethanol (Preparation 47, 0.125 g) were added to a suspension of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.150 g) in DMF (10 mL). The reaction mixture was heated to 90° C. for 1 h. The reaction mixture was allowed to cool to room temperature, poured into water (25 mL), and was extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2, 97/3, 9515). The product was then recrystallized from ethyl acetate and then methanol to yield 0.106 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 154-159° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.64, 8.48, 8.29-8.27, 7.94-7.87, 7.70-7.66, 7.62-7.60, 7.57-7.52, 7.41-7.33, 6.85, 5.53, 4.95-4.91, 4.55, 3.74, 3.74-3.72, 2.89-2.85, 2.79-2.74, 2.36; MS (ESI+) m/z 531 (M+H)+.

後処理

  1. temperatureto cool to room temperature
  2. extractionwas extracted with CH2Cl2 (4×25 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2, 97/3, 9515)
  7. customThe product was then recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-3d64effa00864b10a54213f4a4cb4f23
出典データセット
uspto-grants-2005_04
特許番号
US06878705B2

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