Dichloromethane → 2-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxamide

HRID 13285

Reaktionsgleichung

Reaktionsgleichung von HRID 13285
CN(C1C=CC=CN=1)C.C[Si]([N:14]=[C:15]=[O:16])(C)C.C(Cl)Cl.[F:20][C:21]1[CH:47]=[CH:46][C:24]([O:25][C:26]2[C:40]([CH:41]3[CH2:45][CH2:44][CH2:43][NH:42]3)=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:23][CH:22]=1>O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:25][C:26]2[C:40]([CH:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:15]([NH2:14])=[O:16])=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:46][CH:47]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 70696Trimethylsilyl isocyanateHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Produkt 1

HCID 231453492-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2 mg of dimethylaminopyridine and 0.059 ml of trimethylsilyl isocyanate were added in order to a methylene chloride (1 ml) solution of 31.2 mg of 5-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 168, and the reaction liquid was stirred overnight at room temperature. Water was added to the reaction liquid, and extracted with ethyl acetate, and then washed with saturated saline. After dried and concentrated, the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] to obtain the entitled compound as a white solid.

Aufarbeitung

  1. customthe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated saline
  4. customAfter dried
  5. concentrationconcentrated
  6. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]

Quellen und Nachweise

ORD-Eintrag
ord-451f1694396b4bcab57ee743ed2e574c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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