홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

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
노트
인쇄 미리보기

반응식

HRID 1168504 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 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

생성물 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-carboxamide수율 70%

반응 조건

온도
65 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-807d7addab5341a382779e66cf53d1cb
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06624159B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트