Diisopropylethylamine → Tyclopyrazoflor

HRID 512723

반응식

HRID 512723 반응식
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][S:5][CH2:6][CH2:7][C:8]([OH:10])=O.[Cl:13][C:14]1(NCC)[CH:18]=[CH:17][N:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:15]1.[CH:28]([N:31](C(C)C)CC)(C)[CH3:29]>C(OCC)(=O)C>[Cl:13][C:14]1[C:18]([N:31]([CH2:28][CH3:29])[C:8](=[O:10])[CH2:7][CH2:6][S:5][CH2:4][CH2:3][C:2]([F:1])([F:12])[F:11])=[CH:17][N:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:15]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 171658Poly(difluoromethylene), alpha-(2-((2-carboxyethyl)thio)ethyl)-omega-fluoro-HCID 1180221923-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine

생성물 1

HCID 86700627Tyclopyrazoflor수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
27.5 °C

실험 절차

A solution of 3-((3,3,3-trifluoropropyl)thio)propanoic acid (2.18 g, 10.8 mmol) and 3-chloro-N-ethyl-1-(pyridine-3-yl)-1H-pyrazol-amine (2.00 g, 8.98 mmol) in ethyl acetate (16 mL) was cooled to 5° C. Diisopropylethylamine (5.15 mL, 29.6 mmol) was added dropwise at 0-5° C. over 30 minutes, followed by the addition of 2,4,6-tripropyl-trioxatriphosphinane-2,4,-trioxide (4.00 g, 12.6 mmol) over 30 minutes at 0-5° C. The reaction was allowed to warm to 25-30° C. and stirred for 2 h. Upon reaction completion, the reaction mixture was cooled to 0-5° C. and quenched with water (12 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (30 mL). The combined organic layers were concentrated to afford the desired product as an oil (3.40 g, 94%).

후처리

  1. customUpon reaction completion
  2. temperaturethe reaction mixture was cooled to 0-5° C.
  3. customquenched with water (12 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (30 mL)
  6. concentrationThe combined organic layers were concentrated

출처 및 근거

ORD 기록
ord-15f67a1d8a62450fac2f4ac96c817f78
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102654B2

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