2-Aminoethanesulphonamide monohydrochloride → 1-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-sulfamoyl-ethyl)-amide

HRID 919822노트

반응식

HRID 919822 반응식
C[O:2][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)=[C:7]([C:24]#[N:25])[N:6]=1)=O.Cl.[NH2:27][CH2:28][CH2:29][S:30]([NH2:33])(=[O:32])=[O:31].C[O-].[Na+]>CCO>[S:30]([CH2:29][CH2:28][NH:27][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)=[C:7]([C:24]#[N:25])[N:6]=1)=[O:2])(=[O:32])(=[O:31])[NH2:33]

참가 물질

5

반응물 3

HCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 10942334Sodium MethoxideHCID 682972101-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

생성물 1

HCID 917583821-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-sulfamoyl-ethyl)-amide수율 22.6%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
140 °C

실험 절차

A mixture of 1-benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (20 mg, 0.060 mmol), 2-amino-ethanesulfonic acid amide HCl salt (30 mg, 0.24 mmol), and NaOMe (13 mg, 0.23 mmol) in EtOH (2 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 water. 1 M HCl was added with vigorous stirring until pH about 1, and the aqueous layer was extracted with additional EtOAc. The organic layers were combined, dried over MgSO4, and concentrated. The crude product was first purified by column chromatography (0-5% MeOH/CH2Cl2), then by preparative TLC (10% MeOH/CH2Cl2) to give 5.8 mg of the title compound. MS: (−) m/z 426.24 (M−1).

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc and water
  3. addition1 M HCl was added
  4. extractionthe aqueous layer was extracted with additional EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was first purified by column chromatography (0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-c554f4b319fd47b6989f24016bb81302
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271970B2

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