2-Aminoethanesulphonamide monohydrochloride → 7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid (2-sulfamoyl-ethyl)-amide

HRID 919807노트

반응식

HRID 919807 반응식
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].Cl.[NH2:25][CH2:26][CH2:27][S:28]([NH2:31])(=[O:30])=[O:29].C[O-].[Na+]>CCO>[S:28]([CH2:27][CH2:26][NH:25][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4])(=[O:30])(=[O:29])[NH2:31]

참가 물질

5

반응물 3

HCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 10942334Sodium MethoxideHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

생성물 1

HCID 601512647-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid (2-sulfamoyl-ethyl)-amide수율 53.8%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
140 °C

실험 절차

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (30 mg, 0.097 mmol), 2-amino-ethanesulfonic acid amide HCl salt (24 mg, 0.19 mmol), and NaOMe (9.9 mg, 0.18 mmol) in EtOH (2 mL) was heated at 140° C. for 6 h in a microwave reactor. Solvent was evaporated in vacuo, and the residue was partitioned between 1 M HCl and EtOAc. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined and dried over MgSO4. After evaporating the solvent, the crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 21 mg of the title compound. MS: (+) m/z 403.25 (M+1).

후처리

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between 1 M HCl and EtOAc
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-6fbad10ea39e464e81273e5eb5ee1ecc
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271970B2

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