1,2-Dichloroethane → 2-fluoro-6-methoxy-N-[1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide

HRID 1012137

Reaktionsgleichung

Reaktionsgleichung von HRID 1012137
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=O.[CH3:13][O:14][C:15]1[CH:43]=[CH:42][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([NH2:25])[C:22]([C:26]3[NH:30][C:29]4[CH:31]=[CH:32][C:33]([CH2:35][N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[CH:34][C:28]=4[N:27]=3)=[N:21]2)=[CH:17][CH:16]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH:25][C:23]1[C:22]([C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([CH2:35][N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[CH:34][C:28]=3[N:27]=2)=[N:21][N:20]([CH2:19][C:18]2[CH:42]=[CH:43][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH:24]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27373602-Fluoro-6-methoxybenzoic acidHCID 1784908051-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine

Produkt 1

HCID 1784908092-fluoro-6-methoxy-N-[1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamideAusbeute 116,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-6-methoxy-benzoic acid (20 mg, 0.12 mmol), 1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.12 mmol), EDC (116 mg, 0.14 mmol) and HOBt (81 mg, 0.14 mmol) was stirred at room temperature in DMF (2 ml) for 20 h. The mixture was reduced in vacuo and the residue partitioned between EtOAc (5 ml) and water (2 ml) and the organic portion washed with saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc] to give 2-fluoro-6-methoxy-N-[1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide as a white solid (80 mg, 61%).

Aufarbeitung

  1. customthe residue partitioned between EtOAc (5 ml) and water (2 ml)
  2. washthe organic portion washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried (MgSO4)
  4. customThe residue was purified by flash column chromatography [SiO2, EtOAc]

Quellen und Nachweise

ORD-Eintrag
ord-58982af27e744215af82f12c374b6a66
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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