N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamide → N-(4-Chlorobenzyl)-6-(3-hydroxypropyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067983노트

반응식

HRID 1067983 반응식
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:25])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[H][H]>[Pt].C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:25])[CH:11]=2)=[O:9])=[CH:26][CH:27]=1

참가 물질

5

반응물 2

HCID 11740538N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 9800255N-(4-Chlorobenzyl)-6-(3-hydroxypropyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide수율 89.1%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A mixture of 0.50 g of N-(4-chlorobenzyl)-6-(3-hydroxy-1-propynyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Example No. 31 and 50 mg of 5% platinum on carbon catalyst in 20 mL of 1:1 THF-methanol is stirred under 1 atm hydrogen for 3 h, then filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure and the residual solid flash chromatographed on silica gel using 4-5% methanol in dichloromethane to afford 0.45 g of the title compound as a yellow solid. Further purification is achieved by recrystallization of the solid from 15 mL of acetonitrile.

후처리

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residual solid flash chromatographed on silica gel using 4-5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-fe153a5ea78d4b94882bbb0fabddbf55
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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