Thionyl Chloride → 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640977

Reaktionsgleichung

Reaktionsgleichung von HRID 640977
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([OH:11])=O.S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[C:20]([C:22]1[CH:30]=[C:29]2[C:25]([CH2:26][C:27](=[O:31])[NH:28]2)=[CH:24][CH:23]=1)=[O:21]>C1COCC1>[O:31]=[C:27]1[CH2:26][C:25]2[C:29](=[CH:30][C:22]([C:20]([C:19]3[CH:18]=[C:17]([NH:16][C:9]([C:3]4[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=4[Cl:1])=[O:11])[CH:34]=[CH:33][CH:32]=3)=[O:21])=[CH:23][CH:24]=2)[NH:28]1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 27796525-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acidHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 866104185-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
79 °C

Versuchsvorschrift

A dry 25 mL flask was charged with 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid (0.180 g, 0.873 mmol) and thionyl chloride (10 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by rotary evaporation. The crude acid chloride dissolved in THF (5 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.200 g, 0.794 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 2 h. The reaction mixture was then allowed to cool to room temperature and the precipitate was filtered and washed with THF (˜5 mL) affording pure 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.233 g, 0.571 mmol, 72%).

Aufarbeitung

  1. customThe thionyl chloride was then removed by rotary evaporation
  2. dissolutionThe crude acid chloride dissolved in THF (5 mL)
  3. temperatureto reflux for 2 h
  4. temperatureto cool to room temperature
  5. filtrationthe precipitate was filtered
  6. washwashed with THF (˜5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6e4c16b4654b47e2afb3c8da21984ad9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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