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

反応式

HRID 901257 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-29564bd823e6442aa6cea2482aa468ea
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

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