1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1742935

반응식

HRID 1742935 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](Cl)[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1.Cl.[N:28]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][N:30]=[N:29]1.C1CCN2C(=NCCC2)CC1>CC#N.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16]([N:35]3[CH2:36][CH2:37][CH:33]([N:28]4[CH:32]=[CH:31][N:30]=[N:29]4)[CH2:34]3)[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1268243Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

생성물 1

HCID 19006029Ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of ethyl 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (91 mg, 0.5 mmol), 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (259 mg, 1.5 mmol), and DBU (380 mg, 2.5 mmol) in CH3CN (20 ml) was heated under reflux for 2 h, cooled to r.t. and stirred further for 18 h, diluted with water. Unreacted starting materials were removed by extraction with chloroform. The water layer was concentrated to give a yellow oil. Yield: 150 mg, 62%. 1H NMR (CDCl3) δ: 1.3 (t, 3H), 2.5 (m, 2H), 3.9 (m, 4H), 4.4 (q, 2H), 5.3 (m, 1H), 7.3 (m, 4H), 7.8 (d, 1H), 8.0 (d, 1H), 8.4 (s, 1H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customwere removed by extraction with chloroform
  4. concentrationThe water layer was concentrated
  5. customto give a yellow oil

출처 및 근거

ORD 기록
ord-1ae0aa91e5ae44649d90c58ae0286871
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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