Triethylamine → N-Des(isobutyraldehyde) Pyflubumide

HRID 1952265

반응식

HRID 1952265 반응식
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](Cl)=[O:9])[C:4]([CH3:11])=[N:3]1.[CH2:12]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[C:23]([O:32][CH3:33])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])[NH2:19])[CH:13]([CH3:15])[CH3:14].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:12]([C:16]1[CH:17]=[C:18]([NH:19][C:8]([C:5]2[C:4]([CH3:11])=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:9])[CH:20]=[CH:21][C:22]=1[C:23]([O:32][CH3:33])([C:24]([F:27])([F:25])[F:26])[C:28]([F:29])([F:30])[F:31])[CH:13]([CH3:15])[CH3:14]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chlorideHCID 866190033-Isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

생성물 1

HCID 86629858N-Des(isobutyraldehyde) Pyflubumide수율 80%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

1,3,5-trimethylpyrazole-4-carbonyl chloride (3.93 g, 22.8 mmol), 3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (5.0 g, 15.2 mmol), and triethylamine (3.07 g, 30.4 mmol) were dissolved in tetrahydrofuran (100 ml), and the mixture was heated under reflux for 5 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crude crystals were washed with ether to give the desired compound (5.62 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude crystals
  7. washwere washed with ether

출처 및 근거

ORD 기록
ord-fc21d52197af4bf697b743186097cfcb
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404861B2

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