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

HRID 557410
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HRID 557410 반응식
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=O)=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2.[C:17]([CH:19]=[C:20]([O-])[CH3:21])#[N:18].[Na+].[NH2:24][C:25]([CH3:34])=[CH:26][C:27](=[O:33])[CH2:28][CH:29]1[CH2:32][CH2:31][CH2:30]1.C(O)(=O)C>CC(O)C>[CH:29]1([CH2:28][C:27]([C:26]2[CH:13]([C:9]3[CH:10]=[C:11]([F:12])[C:2]([F:1])=[C:3]4[C:8]=3[O:7][C:6]([CH3:15])=[CH:5][C:4]4=[O:16])[C:19]([C:17]#[N:18])=[C:20]([CH3:21])[NH:24][C:25]=2[CH3:34])=[O:33])[CH2:32][CH2:31][CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 669915394-Amino-1-cyclobutylpent-3-en-2-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

생성물 1

HCID 159792245-(Cyclobutylacetyl)-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carbonitrile

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 85.44 mg (0.45 mmol) of 4-amino-1-cyclobutylpent-3-en-2-one (example 13, stage a) and 0.04 ml (0.67 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). 70.9 mg (37.44% of theory) of the title compound are obtained as yellow crystals.

후처리

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customThe residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)

출처 및 근거

ORD 기록
ord-76951e2d80f04760a8706f0bdfa884a0
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08058447B2

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