1,1'-Carbonyldiimidazole → Tyclopyrazoflor

HRID 512722

反応式

HRID 512722 の反応式
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][S:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(N1C=CN=C1)([N:15]1[CH:19]=[CH:18]N=C1)=O.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]([CH2:19][CH3:18])[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

参加物

6

反応物 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

生成物 1

HCID 86700627Tyclopyrazoflor収率 86.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
20 °C

実験手順

A 20 mL vial was charged with 3-((3,3,3-trifluropropyl)thio)propanoic acid (0.999 g, 4.94 mmol) and acetonitrile (5 mL). Carbonyldiimidazole (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-(pyridine-3-yl)-1H-pyrazol-amine (1.00 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%).

後処理

  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

出典と根拠

ORDレコード
ord-741a8f3ef29e406d895974733664c2fe
出典データセット
uspto-grants-2015_08
特許番号
US09102654B2

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