ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethylformamide → N-[(4-chlorophenyl)methyl]-1-methyl-8-[3-(5-methylimidazol-1-yl)prop-1-ynyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 2086619
ノート
印刷プレビュー

反応式

HRID 2086619 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.Br.[CH3:33][C:34]1[N:38]([CH2:39][C:40]#[CH:41])[CH:37]=[N:36][CH:35]=1.CN(C=O)C>N(CC)CC.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:38]4[C:34]([CH3:33])=[CH:35][N:36]=[CH:37]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 3

HCID 6228DimethylformamideHCID 12095879N-(4-chlorobenzyl)-8-iodo-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamideHCID 227245555-methyl-1-prop-2-ynyl-1H-imidazole hydrobromide

生成物 1

HCID 5278419N-[(4-chlorophenyl)methyl]-1-methyl-8-[3-(5-methylimidazol-1-yl)prop-1-ynyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide収率 29.7%

試薬・触媒・溶媒 3

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

実験手順

To a solution 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) is added 5-methyl-1-prop-2-ynyl-1H-imidazole hydrobromide (120.4 mg). Anhydrous DMF (10 mL) is added to help solubilize the reactants (also requires sonication). The reaction is stirred at room temperature overnight, then condensed. The resulting residue is placed under high vacuum to remove residual DMF. The crude product is dissolved in CH2Cl2 and partitioned between CH2Cl2 and saturated NaHCO3. The layers are separated. The aqueous layer is extracted with CH2Cl2 (2×). The combined organic layers are dried over Na2SO4, filtered, and condensed. The crude product is adsorbed onto silica and chromatographed (eluant 1% MeOH in CH2Cl2 (1L), 2% MeOH in CH2Cl2 (1L), 3% MeOH in CH2Cl2 (1L), 4% MeOH in CH2Cl2 (2L), and 6% MeOH in CH2Cl2 (1L)). Product-containing fractions are combined and concentrated to afford a residue. The residue is recrystallized from hot acetonitrile to afford 87.7 mg of the title compound as a tan solid.

後処理

  1. customalso requires sonication)
  2. customcondensed
  3. customto remove residual DMF
  4. dissolutionThe crude product is dissolved in CH2Cl2
  5. custompartitioned between CH2Cl2 and saturated NaHCO3
  6. customThe layers are separated
  7. extractionThe aqueous layer is extracted with CH2Cl2 (2×)
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. filtrationfiltered
  10. customcondensed
  11. customchromatographed (eluant 1% MeOH in CH2Cl2 (1L), 2% MeOH in CH2Cl2 (1L), 3% MeOH in CH2Cl2 (1L), 4% MeOH in CH2Cl2 (2L), and 6% MeOH in CH2Cl2 (1L))
  12. concentrationconcentrated
  13. customto afford a residue
  14. customThe residue is recrystallized from hot acetonitrile

出典と根拠

ORDレコード
ord-eb79627e10524abd860b44641d0da6b0
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…

このページの内容参加物実験手順後処理出典と根拠反応ノート