Triethylamine → HCID 69217711, 화합물

HRID 901239노트

반응식

HRID 901239 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:36]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1[Cl:36])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59699551HCID 59699551, 화합물

생성물 1

HCID 69217711HCID 69217711, 화합물수율 95%

실험 절차

A solution of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) (0.40 g, 1.13 mmol) and triethylamine (393 μL, 2.82 mmol) was heated in neat POCl3 at 90° C. for 3 h. 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 400 mg (95%) of 4-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (14) as white solids. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.62 (s, 3H), 4.30 (q, J=7.0 Hz, 2H), 5.47 (s, 2H), 6.81 (d, J=7.7 Hz, 2H), 7.21 (d, J=7.6 Hz, 2H), 7.31 (d, J=7.6 Hz, 1H), 8.40 (dd, J=1.5, 7.5 Hz, 1H), 8.71 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 373 (M+1).

후처리

  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

출처 및 근거

ORD 기록
ord-102a2722949b4c77a561e24f2d47cf33
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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