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4,5-Dichloro-1-prop-2-ynylimidazole → N-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)prop-1-ynyl]-1-methyl-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 2086618
ノート
印刷プレビュー

反応式

HRID 2086618 の反応式
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14](I)[CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Cl:32][C:33]1[N:34]=[CH:35][N:36]([CH2:39][C:40]#[CH:41])[C:37]=1[Cl:38]>N(CC)CC.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([C:41]#[C:40][CH2:39][N:36]4[C:37]([Cl:38])=[C:33]([Cl:32])[N:34]=[CH:35]4)[CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 50567354,5-Dichloro-1-prop-2-ynylimidazoleHCID 12095879N-(4-chlorobenzyl)-8-iodo-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide

生成物 1

HCID 5278418N-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)prop-1-ynyl]-1-methyl-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide収率 6.1%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 6228Dimethylformamide溶媒
HCID 8021Diethylamine溶媒

実験手順

To a suspension of N-(4-chlorobenzyl)-8-iodo-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (300 mg), PdCl2(PPh3)2 (19.1 mg), and CuI (5.2 mg) in Et2NH (6.2 mL) and anhydrous DMF (10 mL) is added 4,5-dichloro-1-prop-2-ynylimidazole (104.8 mg). The reaction is sonicated and stirred at room temperature for 2 days. The reaction is condensed to afford a residue. The residue is adsorbed onto silica and chromatographed (eluant 100% CH2Cl2 (1L), 0.5% MeOH in CH2Cl2 (1L), 1% MeOH in CH2Cl2 (1L), 1.5% MeOH in CH2Cl2 (1L), and 2% MeOH in CH2Cl2 (3L)). Product-containing fractions are combined and condensed to afford 20 mg of the title compound as a white solid.

後処理

  1. customThe reaction is sonicated
  2. customcondensed
  3. customto afford a residue
  4. customchromatographed (eluant 100% CH2Cl2 (1L), 0.5% MeOH in CH2Cl2 (1L), 1% MeOH in CH2Cl2 (1L), 1.5% MeOH in CH2Cl2 (1L), and 2% MeOH in CH2Cl2 (3L))
  5. customcondensed

出典と根拠

ORDレコード
ord-bcd9e8bce30e461e8e68ff974742f57b
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06727248B2

反応ノート

読み込み中…

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