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

HRID 557407ノート

反応式

HRID 557407 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.CC(O)C.[C:20]([CH:22]=[C:23]([O-])[CH3:24])#[N:21].[Na+].[NH2:27][C:28]([CH3:38])=[CH:29][C:30](=[O:37])[CH2:31][CH2:32][CH:33]1[CH2:36][CH2:35][CH2:34]1.C(O)(=O)C>>[CH:33]1([CH2:32][CH2:31][C:30]([C:29]2[CH:12]([C:9]3[CH:10]=[CH:11][C:2]([F:1])=[C:3]4[C:8]=3[O:7][C:6]([CH3:14])=[CH:5][C:4]4=[O:15])[C:22]([C:20]#[N:21])=[C:23]([CH3:24])[NH:27][C:28]=2[CH3:38])=[O:37])[CH2:34][CH2:35][CH2:36]1

参加物

6

反応物 5

HCID 176Acetic AcidHCID 3776IsopropanolHCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 669918105-Amino-1-cyclobutylhex-4-en-3-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

生成物 1

HCID 159792215-(3-Cyclobutylpropanoyl)-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carbonitrile

実験手順

A solution of 100 mg (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 81.12 mg (0.49 mmol) of 5-amino-1-cyclobutylhex-4-en-3-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). 60.2 mg (29.5% 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-d1bc7ef247644a8ca2d753b796406cdc
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…