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

반응식

HRID 1951399 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87b23c5087fb471ebdb609b605c70139
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404709B2

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