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

HRID 557399노트

반응식

HRID 557399 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]([CH3:33])=[CH:25][C:26]([O:28][CH:29]1[CH2:32][CH2:31][CH2:30]1)=[O:27].C(O)(=O)C>CC(O)C>[C:16]([C:18]1[CH:12]([C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:14])=[CH:5][C:4]3=[O:15])[C:25]([C:26]([O:28][CH:29]2[CH2:32][CH2:31][CH2:30]2)=[O:27])=[C:24]([CH3:33])[NH:23][C:19]=1[CH3:20])#[N:17]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 66991239Cyclobutyl 3-aminobut-2-enoateHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

생성물 1

HCID 15979089Cyclobutyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

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, 75.28 mg (0.49 mmol) of cyclobutyl 3-aminobut-2-enoate 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 beige-colored crystals are filtered off with suction and dried at 40° C. in a vacuum drying oven. 120.5 mg (60.8% 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 beige-colored crystals are filtered off with suction
  9. customdried at 40° C. in a vacuum
  10. customdrying oven

출처 및 근거

ORD 기록
ord-8f01e4884a2a455486c3df1d98fc2341
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058447B2

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