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

HRID 1742980

반응식

HRID 1742980 반응식
Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:38])=[C:34](Cl)[N:35]=3)[C:30](=[O:39])[C:29]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:28]2)[CH2:26][CH2:25]1>C(#N)C.N1C=CC=CC=1>[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:38])=[C:34]([N:10]4[CH2:11][CH2:12][CH:7]([N:2]5[CH:6]=[CH:5][N:4]=[N:3]5)[CH2:8][CH2:9]4)[N:35]=3)[C:30](=[O:39])[C:29]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:28]2)[CH2:25][CH2:26]1

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 190060184-(1H-1,2,3-triazol-1-yl)piperidine hydrochloride

생성물 1

HCID 19005933Ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate수율 66%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

4-(1,2,3-triazol-1-yl)piperidine hydrochloride (225 mg, 1.2 mmol) and DBU (182 mg, 1.2 mmol) was added to a suspension of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100° C. for 5 hrs. The suspended solid was filtered and the filtrate was concentrated to dryness. The residue was triturated with water and separated solid was filtered, washed with water and dried to give 135 mg of desired product. m.p. 213°-214° C.; 1H NMR (CDCl3) δ: 8.48 (s, 1H), 8.11 (d, 1H), 7.72 (s, 1H), 7.60 (s, 1H), 4.60-4.85 (m, 3H), 4.29-4.40 (q, 2H), 3.43-3.54 (m, 1H), 3.21-3.35 (m, 2H), 2.10-2.36 (m, 4H), 1.36 (t, 3H), 0.95-1.23 (m, 4H).

후처리

  1. filtrationThe suspended solid was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was triturated with water
  4. customseparated solid
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-11c49ca4866945bca119484875332fd1
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

연결된 노트

불러오는 중…