Methyl iodide → N-(4-chlorobenzyl)-6-(hydroxymethyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1264992노트

반응식

HRID 1264992 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][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][OH:22])=[CH:15][C:14]=3[I:23])=[O:9])=[CH:4][CH:3]=1.[C:26]([O-])([O-])=O.[K+].[K+].CI.CO.C(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([I:23])[CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=3)[N:12]([CH3:26])[CH:11]=2)=[O:9])=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 178522929HCID 178522929, 화합물

생성물 1

HCID 22724554N-(4-chlorobenzyl)-6-(hydroxymethyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide수율 54%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-8-iodo-3-quinolinecarboxamide(6.5 g) in anhydrous DMF (116.7 mL) is heated to 65° C. to solubilize the starting material. The solution is allowed to cool to room temperature. To this solution is added K2CO3 (7.68 g) and CH3I (8.65 mL). The reaction is stirred at room temperature overnight. The reaction is poured into H20 (1L) to precipitate the product. The solid is filtered, adsorbed onto silica, and chromatographed in 2 batches (eluent 100% CH2Cl2 (3L), 0.5% MeOH in CH2Cl2 (1L), and 1% MeOH in CH2Cl2 (9L)). Product-containing fractions are combined and condensed to afford 3.6 g (54%) of the desired product as a white solid.

후처리

  1. customto precipitate the product
  2. filtrationThe solid is filtered
  3. customchromatographed in 2 batches (eluent 100% CH2Cl2 (3L), 0.5% MeOH in CH2Cl2 (1L), and 1% MeOH in CH2Cl2 (9L))
  4. customcondensed

출처 및 근거

ORD 기록
ord-89b127be896448f99475095110b208bc
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544990B2

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