1,2-Dichloroethane → Ethyl 7-chloro-1-(2,4-difluoro-5-methylaminophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1415936노트

반응식

HRID 1415936 반응식
[NH2:1][C:2]1[C:3]([F:27])=[CH:4][C:5]([F:26])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:19])=[C:15]([Cl:18])[N:16]=3)[C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]2)[CH:7]=1.Cl[CH2:29]CCl.CO.C=O>[Pd].C(O)(=O)C>[Cl:18][C:15]1[N:16]=[C:17]2[C:12]([C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9][N:8]2[C:6]2[CH:7]=[C:2]([NH:1][CH3:29])[C:3]([F:27])=[CH:4][C:5]=2[F:26])=[CH:13][C:14]=1[F:19]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 887MethanolHCID 53833255Ethyl 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

생성물 1

HCID 54102467Ethyl 7-chloro-1-(2,4-difluoro-5-methylaminophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

Ethyl 1-(5-amino-2,4-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (500 mg) was added to a mixture of 10 ml of 1,2-dichloroethane, 5 ml of methanol and 0.5 ml of acetic acid together with 100 mg of 37% formalin. Using 0.08 g of 10% palladium on carbon, hydrogenation was carried out for 16 hours. After the catalyst was filtered off, the filtrate was concentrated in vacua. The residue was dissolved in 50 ml of chloroform, washed with an aqueous solution of 50% sodium carbonate, dried over anhydrous magnesium sulfate, and then concentrated in vacua. The residue was subject to chromatography using 20 g of silica gel (eluting solution: chloroform) to give 150 mg of the title compound.

후처리

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacua
  3. dissolutionThe residue was dissolved in 50 ml of chloroform
  4. washwashed with an aqueous solution of 50% sodium carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacua

출처 및 근거

ORD 기록
ord-4039d01e4f784e4caa8c82d93150cfef
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910498

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