Triethylamine → HCID 59699661、化合物

HRID 901292ノート

反応式

HRID 901292 の反応式
C(N(CC)CC)C.[CH2:8]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[C:18](O)=[C:17]([S:26]([CH3:29])(=[O:28])=[O:27])[C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O=P(Cl)(Cl)[Cl:33]>>[CH2:8]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[C:18]([Cl:33])=[C:17]([S:26]([CH3:29])(=[O:28])=[O:27])[C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

4

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59699592HCID 59699592、化合物

生成物 1

HCID 59699661HCID 59699661、化合物

反応条件

温度
90 °C

実験手順

Triethylamine (1.2 mL, 8.6 mmol) was added to a suspension of 1-benzyl-4-hydroxy-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (114) (0.94 g, 2.9 mmol) in neat POCl3 and heated at 90° C. for 3 h. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in water, neutralized by solid NaHCO3, and extracted by dichloromethane. The organic layer was subsequently washed by saturated NaHCO3 solution, water and brine, dried over Na2SO4, and evaporated to yield 1-benzyl-4-chloro-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (115) as yellow solid. Yield 0.92 g (92%), mp 191° C. 1H-NMR (DMSO-d6): δ 3.50 (s, 3H), 5.65 (s, 2H), 7.28 (m, 5H), 7.55 (m, 1H), 8.70 (dd, J=1.6, 8.4 Hz, 1H), 8.84 (dd, J=1.6, 4.4 Hz, 1H); EIMS m/z 349 (M+1).

後処理

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. extractionextracted by dichloromethane
  4. washThe organic layer was subsequently washed by saturated NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-130a248aa3944a16b8d1889dfa2229e5
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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