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 919822ノート

反応式

HRID 919822 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c554f4b319fd47b6989f24016bb81302
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

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