Acetic Acid → 4-(5-Fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(4-methylpentanoyl)-1,4-dihydropyridine-3-carbonitrile

HRID 557406ノート

反応式

HRID 557406 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[C:16]([CH:18]=[C:19]([O-])[CH3:20])#[N:17].[Na+].[NH2:23][C:24](=[CH:26][C:27](=[O:33])[CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:25].C(O)(=O)C>CC(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]2[C:26]([C:27](=[O:33])[CH2:28][CH2:29][CH:30]([CH3:31])[CH3:32])=[C:24]([CH3:25])[NH:23][C:19]([CH3:20])=[C:18]2[C:16]#[N:17])=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 714061112-Amino-7-methyloct-2-en-4-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

生成物 1

HCID 159792204-(5-Fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(4-methylpentanoyl)-1,4-dihydropyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 100 mg (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 75.3 mg (0.49 mmol) of 2-amino-7-methyloct-2-en-4-one and 0.04 ml (0.73 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is crystallized from diethyl ether. The yellow crystals are filtered off with suction and purified further on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). 75.2 mg (38.1% of theory) of the title compound are obtained.

後処理

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. washwashed with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is crystallized from diethyl ether
  8. filtrationThe yellow crystals are filtered off with suction
  9. custompurified further on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)

出典と根拠

ORDレコード
ord-d985b3432eaa4ba784bfb690329183de
出典データセット
uspto-grants-2011_11
特許番号
US08058447B2

反応ノート

読み込み中…