Triethylamine → 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

HRID 549239노트

반응식

HRID 549239 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([N:17]1[C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:20][C:19]([C:29]([NH2:31])=O)=[N:18]1)[CH2:15][CH3:16].C(N(CC)CC)C>ClCCl>[CH2:14]([N:17]1[C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:20][C:19]([C:29]#[N:31])=[N:18]1)[CH2:15][CH3:16]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 671577891-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide

생성물 1

HCID 671577501-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile수율 106%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of trifluoroacetic anhydride (2.50 mL, 17.7 mmol) in dichloromethane (32 mL) was added over a period of ten minutes to a 0° C. solution of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide (4.05 g, 16.1 mmol) and triethylamine (4.89 g, 48.3 mmol) in dichloromethane (32 mL). After the addition was complete, the cooling bath was removed and the solution was stirred for three hours. The solution was washed with 2 M aqueous sodium carbonate. The aqueous layer was extracted three times with tert-butyl methyl ether. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (eluting with 40% to 70% ethyl acetate in hexane) to provide 3.98 g of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile as a pale yellow oil.

후처리

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. washThe solution was washed with 2 M aqueous sodium carbonate
  4. extractionThe aqueous layer was extracted three times with tert-butyl methyl ether
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by automated flash chromatography (eluting with 40% to 70% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-06267feec9794738995cf08950a373d3
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943636B2

반응 노트

불러오는 중…