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Dimethylformamide → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-(3-hydroxy-1-propynyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

HRID 1168504
ノート
印刷プレビュー

反応式

HRID 1168504 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([CH2:22][CH:23]([CH2:24][OH:25])[N:12]4[CH:11]=2)[CH:15]=[C:16](I)[CH:17]=3)=[O:9])=[CH:4][CH:3]=1.CN([CH:31]=[O:32])C.[CH2:33](N(CC)CC)[CH3:34]>>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([CH2:22][CH:23]([CH2:24][OH:25])[N:12]4[CH:11]=2)[CH:15]=[C:16]([C:33]#[C:34][CH2:31][OH:32])[CH:17]=3)=[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

4

反応物 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 12083028N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

生成物 1

HCID 10137080N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-(3-hydroxy-1-propynyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide収率 70%

反応条件

温度
65 °C

実験手順

A solution containing N-(4-chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide (Preparation 10, 0.15 g), anhydrous DMF (6 mL), and triethylamine (0.8 mL) is purged with nitrogen three times before adding propargyl alcohol (19 μL), copper(I)iodide (14 mg), and PdCl2(PPh3)2 (8 mg). The solution is heated to 65° C. and then is cooled, diluted with CH2Cl2 (25 mL), and poured into water (30 mL). The organic layer is washed with brine, dried (Na2SO4), filtered, and concentrated to give a brown residue. The crude product is chromatographed eluting with 0-6% methanol in CH2Cl2 (250 mL each) to give 90 mg (70%) of the title compound as a white solid. Physical characteristics: M.p. 224-225° C.; MS (ESI+) m/z 423 (M+H)+.

後処理

  1. customis purged with nitrogen three times
  2. additionbefore adding propargyl alcohol (19 μL), copper(I)iodide (14 mg), and PdCl2(PPh3)2 (8 mg)
  3. temperatureis cooled
  4. additiondiluted with CH2Cl2 (25 mL)
  5. additionpoured into water (30 mL)
  6. washThe organic layer is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a brown residue
  11. customThe crude product is chromatographed
  12. washeluting with 0-6% methanol in CH2Cl2 (250 mL each)

出典と根拠

ORDレコード
ord-807d7addab5341a382779e66cf53d1cb
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06624159B2

反応ノート

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