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2-Furancarbonyl chloride → 1-(4-Fluorob-enzyl)-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-6-methyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrile

HRID 346601
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HRID 346601 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[F:9][C:10]1[CH:36]=[CH:35][C:13]([CH2:14][N:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[C:18]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[C:17]([C:32]#[N:33])[C:16]2=[O:34])=[CH:12][CH:11]=1>N1C=CC=CC=1>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[C:18]([N:26]3[CH2:31][CH2:30][N:29]([C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[O:7])[CH2:28][CH2:27]3)=[C:17]([C:32]#[N:33])[C:16]2=[O:34])=[CH:35][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 682422-Furancarbonyl chlorideHCID 210818991-(4-Fluoro-benzyl)-6-methyl-2-oxo-4-(piperazin-1-yl)-1,2-dihydro-quinolin-3-carbonitrile

생성물 1

HCID 587992381-(4-Fluorob-enzyl)-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-6-methyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrile수율 85%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2-Furoyl chloride (118 μL, 1.2 mmol) was added to a stirred solution of Compound 27 (300 mg, 0.8 mmol) in pyridine (5 mL) under argon at 0° C. The solution was allowed to come to room temperature and further stirred overnight. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and recrystallized by hexane and ether to yield 320 mg (85%) of white solids. M.P. 276° C. 1H NMR (DMSO-d6): δ 2.37 (s, 3H), 3.69 (m, 4H), 3.97 (m, 4H), 5.45 (s, 2H), 6.67 (dd, J=1.7, 3.7 Hz, 1H), 7.09 (d, J=3.4 Hz, 1H), 7.12 (m, 2H), 7.26 (m, 2H), 7.35 (d, J=8.7 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.71 (s, 1H), 7.89 (s, 1H). EIMS m/z 493 (M+23). Anal. (C27H23FN4O3) C, H, N.

후처리

  1. customto come to room temperature
  2. customthe solids formed
  3. filtrationwere filtered
  4. washThe solids were washed by excess water
  5. customdried
  6. customrecrystallized by hexane and ether

출처 및 근거

ORD 기록
ord-76f26e307efc4754a2d96647dc10ded1
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173036B2

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