1H-pyrazole-4-carbaldehyde → 1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carbaldehyde

HRID 1435491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435491
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:27]1[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[N:28]1>CN(C1C=CN=CC=1)C.ClCCCl>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:27]3[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[N:28]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 51306731H-pyrazole-4-carbaldehydeHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Produkt 1

HCID 579372961-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

2-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (0.8 g, 1.9 mmol) was added to a solution of 1H-pyrazole-4-carbaldehyde (0.6 g, 6.2 mmol) and DMAP (1.5 g, 12 mmol) in DCE (70 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h. The solvent was concentrated and the product was purified by flash chromatography on silica gel using DCM/EtOAc (1:1) as eluent to provide the title compound as white solid. Yield: 0.34 g (36%); MS (ESI) (M+H)+=465.0.

Aufarbeitung

  1. concentrationThe solvent was concentrated
  2. customthe product was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a1c2f44f627f440aae2d5afed01a7572
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615642B2

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