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Sodium Methoxide → 1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]amide

HRID 919859
ノート
印刷プレビュー

反応式

HRID 919859 の反応式
CO[C:3]([C:5]1[C:6]([OH:35])=[C:7]2[C:12](=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:14]=1)[N:11]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10](=[O:28])[C:9]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:8]2)=[O:4].Cl.[NH2:37][CH2:38][CH2:39][N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42].C[O-].[Na+]>CCO>[CH3:44][S:41]([N:40]([CH3:45])[CH2:39][CH2:38][NH:37][C:3]([C:5]1[C:6]([OH:35])=[C:7]2[C:12](=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:14]=1)[N:11]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10](=[O:28])[C:9]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[CH:8]2)=[O:4])(=[O:43])=[O:42]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10942334Sodium MethoxideHCID 54759137N-(2-aminoethyl)-N-methylmethanesulfonamide hydrochlorideHCID 682973711-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

生成物 1

HCID 601516821-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(methanesulfonyl-methyl-amino)-ethyl]amide収率 53.7%

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-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (38.5 mg, 0.083 mmol), N-(2-amino-ethyl)-N-methyl-methanesulfonamide HCl salt (78 mg, 0.42 mmol), and NaOMe (22 mg, 0.42 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 water. 1 M HCl was added until pH was about 3. The aqueous layer was extracted with additional EtOAc, and the combined organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 26 mg of the title compound. MS: (+) m/z 584.26 (M+1).

後処理

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. addition1 M HCl was added until pH was about 3
  4. extractionThe aqueous layer was extracted with additional EtOAc
  5. dry with materialthe combined organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-37480f33398c4cc5a5e7176b2fecca1d
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09271970B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート