Water → Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 1817329노트

반응식

HRID 1817329 반응식
C(O[C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=1)CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]=[CH:23][C:22]1=[O:27].O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][C:24]2[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=[C:6]([OH:10])[C:23]=2[C:22]1=[O:27]

참가 물질

4

반응물 3

HCID 962WaterHCID 594556041-(3-Chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-oneHCID 66996945Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

생성물 1

HCID 59455599Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

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온도
130 °C

실험 절차

Ethyl 5-butoxy-1,3-oxazole-2-carboxylate (44.5 g, 208.6 mmol) and 1-(3-chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (25 g, 104.3 mmol) were placed in a heavy walled round bottom flask equipped with a screw top and acid resistant O-ring and a stir bar. The mixture was stirred and water (2.82 mL, 156.7 mmol) was added. The reaction was sealed and placed in an oil bath pre-heated to 130° C. The reaction was aged for 72 hours, when LCMS showed much of the lactam had been consumed. The reaction was allowed to cool and sit until the mass had solidified. The mass was taken up in ether and the solids collected by filtration to give the product as a tan solid. The product was further purified by crystallization from EtOAc.

후처리

  1. customequipped with a screw top and acid resistant O-ring and a stir bar
  2. customThe reaction was sealed
  3. customplaced in an oil bath
  4. customhad been consumed
  5. temperatureto cool
  6. filtrationthe solids collected by filtration

출처 및 근거

ORD 기록
ord-e98c8a2841aa45b885ad890db436cb1d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598264B2

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