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Sodium Methoxide → 1-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]amide

HRID 919821
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인쇄 미리보기

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HRID 919821 반응식
CO[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][N:6]=1)=[O:4].Cl.[NH2:25][CH2:26][CH2:27][N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30].C[O-].[Na+]>CCO>[CH3:32][S:29]([N:28]([CH3:33])[CH2:27][CH2:26][NH:25][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][N:6]=1)=[O:4])(=[O:31])=[O:30]
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참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 54759137N-(2-aminoethyl)-N-methylmethanesulfonamide hydrochlorideHCID 682971941-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

생성물 1

HCID 867141271-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]amide수율 54.5%

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
140 °C

실험 절차

A mixture of 1-benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (25 mg, 0.081 mmol), N-(2-amino-ethyl)-N-methyl-methanesulfonamide HCl salt (61 mg, 0.32 mmol), and NaOMe (17 mg, 0.32 mmol) in EtOH (3 mL) was heated at 140° C. for 6 h in a microwave reactor. The mixture was concentrated to dryness, and the residue was partitioned between EtOAc and 0.1 M HCl. The organic layer was dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 19 mg of the title compound as a white solid. MS: (+) m/z 431.34 (M+1).

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc and 0.1 M HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-4825b826246d4474a66144fb3c142648
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09271970B2

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