Hydrochloric Acid → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641455

Reaktionsgleichung

Reaktionsgleichung von HRID 1641455
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([NH:12][CH:13]([CH:15]1[CH2:17][CH2:16]1)[CH3:14])=[O:11].[Br:23][C:24]1[CH:28]=[C:27]([C:29](OCCCCC)=[O:30])[N:26]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:25]=1.Cl>CS(C)=O>[Br:23][C:24]1[CH:28]=[C:27]([C:29]([NH:7][C:8]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=2[C:10](=[O:11])[NH:12][CH:13]([CH:15]2[CH2:17][CH2:16]2)[CH3:14])=[O:30])[N:26]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:25]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 435330962-amino-5-chloro-N-(1-cyclopropylethyl)benzamideHCID 59549434pentyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

Produkt 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamideAusbeute 13,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

0.11 g potassium tert-butoxide was added to a mixed solution comprising 0.19 g of 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide, 0.30 g of pentyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate and 3 ml of dimethyl sulfoxide, followed by reaction at room temperature for 45 minutes. The reaction liquid was slowly added to 40 ml of diluted hydrochloric acid. The mixed liquid was subjected to extraction with ethyl acetate, and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7.5/2.5) to obtain 0.058 g of the desired product (melting point: 231 to 233° C.) in the form of white crystals.

Aufarbeitung

  1. customfollowed by reaction at room temperature for 45 minutes
  2. customThe reaction liquid
  3. extractionThe mixed liquid was subjected to extraction with ethyl acetate
  4. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and with a sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7.5/2.5)

Quellen und Nachweise

ORD-Eintrag
ord-64b25188dd7c4f9b9b2f10ce2c1320db
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08115006B2

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