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 557407노트

반응식

HRID 557407 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d1bc7ef247644a8ca2d753b796406cdc
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058447B2

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