Triethylamine → HCID 59699661, 화합물

HRID 901292노트

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HRID 901292 반응식
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

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59699592HCID 59699592, 화합물

생성물 1

HCID 59699661HCID 59699661, 화합물

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-130a248aa3944a16b8d1889dfa2229e5
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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