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 557406노트

반응식

HRID 557406 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.[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

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-d985b3432eaa4ba784bfb690329183de
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058447B2

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