1,2-Dichloroethane → N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2,6-difluoro-benzamide

HRID 1012054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012054
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:25]([NH2:26])=[CH:24][NH:23][N:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[NH:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]=[C:13]1[C:21]1[C:25]([NH:26][C:4](=[O:6])[C:3]2[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[CH:24][NH:23][N:22]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 97962,6-Difluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, Verbindung

Produkt 1

HCID 178522420N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2,6-difluoro-benzamideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2,6-difluorobenzoic acid (43 mg, 0.28 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.25 mmol), EDC (58 mg, 0.30 mmol) and HOBt (40.5 mg, 0.30 mmol) in DMF (10 ml) was stirred at ambient temperature for 24 h. The mixture was reduced in vacuo, water (30 ml) added and the resultant solid collected by filtration, dried in the vacuum oven and purified by flash column chromatography [SiO2, EtOAc-petrol (1:2, 1:1, 3:1)] affording N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2,6-difluoro-benzamide (20 mg, 24%). (LC/MS: Rt 3.29, [M+H]+ 339.64).

Aufarbeitung

  1. additionadded
  2. filtrationthe resultant solid collected by filtration
  3. customdried in the vacuum oven
  4. custompurified by flash column chromatography [SiO2, EtOAc-petrol (1:2, 1:1, 3:1)]

Quellen und Nachweise

ORD-Eintrag
ord-bc4a8e59b1764704be0851248f93f47d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

Notizen zur Reaktion

Wird geladen…