Potassium Hydroxide → 6-(3-Chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

HRID 17994

반응식

HRID 17994 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:27])[C:10](=[O:26])[N:11]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH3:25])[C:12]=2[C:16]([O:18]C)=[O:17])[C:7]1=[O:28].[OH-].[K+].O1CCCC1CO.O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:27])[C:10](=[O:26])[N:11]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH3:25])[C:12]=2[C:16]([OH:18])=[O:17])[C:7]1=[O:28]

참가 물질

4

반응 조건

온도
50 °C

실험 절차

Methyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (0.18 g, 0.38 mmol) and potassium hydroxide (0.17 g, 2.3 mmol) in a mixture of 1:1:1 v/v/v tetrahydrofuran-methanol-water (4.5 mL) was heated at 50° C. overnight. The reaction mixture was concentrated under vacuum. The residue was partitioned between dichloromethane and dilute hydrochloric acid. The aqueous extract was concentrated under vacuum to provide the title compound as hydrochloride salt. This was used in the following step without further purification. ES MS M+1=452

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between dichloromethane and dilute hydrochloric acid
  3. extractionThe aqueous extract
  4. concentrationwas concentrated under vacuum

출처 및 근거

ORD 기록
ord-edb76f37641c463b8fafa3e58110303d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741315B2

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