1-(Thien-2-ylcarbonyl)piperazine → 6-Methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 346639노트

반응식

HRID 346639 반응식
[N:1]1([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=2)[NH:18][C:17](=[O:26])[C:16]=1[C:27]#[N:28]>C1(C)C=CC=CC=1>[CH3:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:26])[C:16]([C:27]#[N:28])=[C:15]2[N:4]1[CH2:5][CH2:6][N:1]([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 210819634-Chloro-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

생성물 1

HCID 210819836-Methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile수율 92.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

Piperazine-1-yl-thiophen-2-yl-methanone (8.73 g, 41.16 mmol) was added to a solution of Compound 106 (4.5 g, 20.08 mmol) in toluene (50 mL) and heated overnight at 110° C. The solvent was removed under vacuum. The residue was suspended in water, sonicated, and filtered. The crude product was purified by flash chromatography eluting with 0–2% methanol in dichloromethane gradient to yield 7.0 g (92%) of white solids. M.P. 269° C. 1H NMR (DMSO-d6): δ 2.34 (s, 3H), 3.65 (m, 4H), 3.92 (m, 4H), 7.14 (m, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 7.49 (d, J=3.5 Hz, 1H), 7.51 (s, 1H), 7.81 (d, J=4.8 Hz, 1H). EIMS m/z 379 (M+1).

후처리

  1. customThe solvent was removed under vacuum
  2. customsonicated
  3. filtrationfiltered
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 0–2% methanol in dichloromethane gradient

출처 및 근거

ORD 기록
ord-d2efee93178f4fc4b9fc5a1f080614c3
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173036B2

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