Ammonium Chloride → 5-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxamide

HRID 733128

Reaktionsgleichung

Reaktionsgleichung von HRID 733128
[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH:13]=[CH:14][CH:15]=2)[N:8]=[C:7]([C:23]([OH:25])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:32]C=2C=1.C(N(CC)C(C)C)C.[Cl-].[NH4+]>CN(C=O)C>[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH:13]=[CH:14][CH:15]=2)[N:8]=[C:7]([C:23]([NH2:32])=[O:25])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 521913N,N-Diethyl-2-propanamineHCID 112796905-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

Produkt 1

HCID 113826455-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxamideAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the carboxylic acid (0.062 g, 0.17 mmol) in DMF (1 ml) were added pyBOP (0.138 g, 0.26 mmol), HOBT (0.035 g, 0.2 mmol), diethylisopropylamine (0.147 ml, 0.87 mmol) and ammonium chloride (0.056 g, 1.05 mmol). The reaction mixture was stirred at room temperature for 16 hours, then cooled and partitioned between ethylacetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification of the crude product by silica-gel chromatography (3:2 hexanes/ethylacetate) yielded the product (0.062 g, 64%) as a solid.

Aufarbeitung

  1. temperaturecooled
  2. custompartitioned between ethylacetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude product by silica-gel chromatography (3:2 hexanes/ethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-be7ac90ca35c4ec0ad5442cbff5b3004
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589116B2

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