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Sodium Methoxide → 1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]-amide

HRID 919824
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HRID 919824 반응식
CO[C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:8]2)=[O:4].Cl.[NH2:31][CH2:32][CH2:33][N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36].C[O-].[Na+]>CCO>[CH3:38][S:35]([N:34]([CH3:39])[CH2:33][CH2:32][NH:31][C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:8]2)=[O:4])(=[O:37])=[O:36]
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참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 54759137N-(2-aminoethyl)-N-methylmethanesulfonamide hydrochlorideHCID 682973581-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

생성물 1

HCID 601514021-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]-amide수율 34.6%

시약·촉매·용매 1

HCID 702
Ethanol
용매

반응 조건

온도
140 °C

실험 절차

A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (25 mg, 0.065 mmol), N-(2-amino-ethyl)-N-methyl-methanesulfonamide HCl salt (49 mg, 0.26 mmol), and NaOMe (14 mg, 0.26 mmol) in EtOH (3 mL) was heated at 140° C. for 6 h in a microwave reactor. Solvent was evaporated in vacuo, and the residue was partitioned between EtOAc and 0.1 M HCl. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined and dried over MgSO4. After evaporating the solvent, the residue was purified by silica gel chromatography (0-3% MeOH/CH2Cl2) to give 11.4 mg of the title compound as a light yellow solid. MS: (+) m/z 507.36 (M+1).

후처리

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and 0.1 M HCl
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe residue was purified by silica gel chromatography (0-3% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-1d157a8f4fe94f2e983f10814d019adf
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09271970B2

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