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

反応式

HRID 1742980 の反応式
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

参加物

6

反応物 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

生成物 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-carboxylate収率 66%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11c49ca4866945bca119484875332fd1
出典データセット
uspto-grants-1994_08
特許番号
US05342846

関連ノート

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