4-Amino-1,2-dihydropyridin-2-one → 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

HRID 1951399

反応式

HRID 1951399 の反応式
[C:1]([C:4]([C:18](=O)[CH3:19])=[CH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]#[N:17])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][NH:25][C:24](=[O:28])[CH:23]=1>C(O)(C)C>[C:1]([C:4]1[CH:5]([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]#[N:17])=[CH:8][CH:7]=2)[C:23]2[C:24](=[O:28])[NH:25][CH:26]=[CH:27][C:22]=2[NH:21][C:18]=1[CH3:19])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 596030144-(2-Acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile

生成物 1

HCID 596030254-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

325 mg (1.23 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile are taken up in 20 ml of isopropanol and, after addition of 151 mg (1.23 mmol) of 4-aminopyridin-2(1H)-one, heated at the reflux temperature for 72 h. The mixture is then concentrated and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). The product fractions are combined, the solvent is removed, and the residue is stirred with diethyl ether. The precipitated product is filtered off and dried under high vacuum. 91 mg (21.2% of theory) of the title compound are obtained.

後処理

  1. temperatureheated at the reflux temperature for 72 h
  2. concentrationThe mixture is then concentrated
  3. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)
  4. customthe solvent is removed
  5. filtrationThe precipitated product is filtered off
  6. customdried under high vacuum

出典と根拠

ORDレコード
ord-87b23c5087fb471ebdb609b605c70139
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

関連ノート

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