Triethylamine → 4,6-Dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901273ノート

反応式

HRID 901273 の反応式
C1([NH:7][C:8]([C:10]2[C:11](=[O:31])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C:13]3[C:18]([C:19]=2O)=[CH:17][C:16]([Cl:21])=[CH:15][N:14]=3)=O)CCCCC1.C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:41]>>[Cl:41][C:19]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([Cl:21])[CH:17]=2)[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:11](=[O:31])[C:10]=1[C:8]#[N:7]

参加物

4

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 692188546-Chloro-4-hydroxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Cyclohexylamide

生成物 1

HCID 692163924,6-Dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile収率 95%

実験手順

A solution of 6-chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid cyclohexylamide (93) (10.6 g, 24 mmol) and triethylamine (8.33 mL, 60 mmol) was heated in neat POCl3 overnight at 90° C. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in saturated NaHCO3 solution, sonicated briefly and filtered. The solids were dissolved in dichloromethane, washed subsequently by saturated NaHCO3 solution, water and brine. The organic phase was dried over MgSO4 and evaporated to yield 8.2 g (95%) of 4,6-dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile (95) as white solids. MP 208° C. 1H-NMR (DMSO-d6): δ 3.69 (s, 3H), 5.50 (s, 2H), 6.82 (m, 2H), 7.87 (m, 2H), 8.59 (d, J=2.8 Hz, 1H), 8.94 (d, J=2.8 Hz, 1H); EIMS m/z 362 (M+2).

後処理

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. dissolutionThe solids were dissolved in dichloromethane
  6. washwashed subsequently by saturated NaHCO3 solution, water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-9c50a52f52bb4f24ab58a6c144a2ad21
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

反応ノート

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