1,1'-Carbonyldiimidazole → Tyclopyrazoflor

HRID 512752

반응식

HRID 512752 반응식
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][S:5][CH2:6][CH2:7][C:8]([OH:10])=O.[CH:13]1N=C[N:15](C(N2C=NC=C2)=O)[CH:14]=1.Cl.N1C=CN=C1.[Cl:31][C:32]1(NCC)[CH:36]=[CH:35][N:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[NH:33]1>C(#N)C>[Cl:31][C:32]1[C:36]([N:15]([CH2:14][CH3:13])[C:8](=[O:10])[CH2:7][CH2:6][S:5][CH2:4][CH2:3][C:2]([F:1])([F:12])[F:11])=[CH:35][N:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[N:33]=1

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 171658Poly(difluoromethylene), alpha-(2-((2-carboxyethyl)thio)ethyl)-omega-fluoro-HCID 10197644Imidazolium chlorideHCID 1180221923-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine

생성물 1

HCID 86700627Tyclopyrazoflor수율 86.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
20 °C

실험 절차

A 20-mL vial was charged with 3-((3,3,3-trifluoropropyl)thio)propanoic acid (0.999 g, 4.94 mmol) and acetonitrile (5 mL). Carbodiimidazole (0.947 g, 5.84 mmol) (off-gassing) and 1H-imidazole hydrochloride (0.563 g, 5.39 mmol) were added and the reaction was stirred at 20° C. for 4 hours. 3-Chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (1 g, 4.49 mmol) was added and the reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis indicated that the conversion was 96%. The reaction was cooled to 20° C. and concentrated to dryness. The residue was purified by flash column chromatography using 80% ethyl acetate/hexanes as eluent. Pure fractions were combined and concentrated to afford a light yellow solid (1.58 g, 86%). Characterization matched sample prepared by previous method.

후처리

  1. stirringthe reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis
  2. temperatureThe reaction was cooled to 20° C.
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash column chromatography
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0be59e62be9f49c0b25a4cdc76f7c0cf
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102655B2

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