4-Chloro-6-fluoro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester → 4-Chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

HRID 901257

반응식

HRID 901257 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8](CC2C=CC(OC)=CC=2)[C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([F:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[NH:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([F:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]

참가 물질

3

반응물 1

HCID 692183544-Chloro-6-fluoro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

생성물 1

HCID 692189084-Chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester수율 98.7%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 4-chloro-6-fluoro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (76) (6.0 g, 15.35 mmol) in neat TFA was refluxed for 3 h. The solution was cooled and the excess TFA was distilled under vacuum. The residue was suspended in saturated NaHCO3 solution, sonicated briefly and filtered. The solids were washed by water, and dried at room temperature to yield 4.1 g (98%) of 4-chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (78) as white solids. MP: 217° C.; 1H-NM (DMSO-d6): 1.28 (t, J=7.2 Hz, 3H), 4.35 (q, J=7.2 Hz, 2H), 8.24 (dd, J=2.8, 8.0 Hz, 1H), 8.75 (d, J=2.8 Hz, 1H), 13.00 (s, 1H); EIMS: 271 (M+1).

후처리

  1. temperatureThe solution was cooled
  2. distillationthe excess TFA was distilled under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. washThe solids were washed by water
  6. customdried at room temperature

출처 및 근거

ORD 기록
ord-29564bd823e6442aa6cea2482aa468ea
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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