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

HRID 13284
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 13284
CN(C1C=CC=CN=1)C.C[Si]([N:14]=[C:15]=[O:16])(C)C.C(Cl)Cl.[CH3:20][S:21]([C:24]1[CH:50]=[CH:49][C:27]([O:28][C:29]2[C:43]([CH:44]3[CH2:48][CH2:47][CH2:46][NH:45]3)=[CH:42][C:32]3[NH:33][C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)=[N:35][C:31]=3[CH:30]=2)=[CH:26][CH:25]=1)(=[O:23])=[O:22]>O>[CH3:20][S:21]([C:24]1[CH:25]=[CH:26][C:27]([O:28][C:29]2[C:43]([CH:44]3[CH2:48][CH2:47][CH2:46][N:45]3[C:15]([NH2:14])=[O:16])=[CH:42][C:32]3[NH:33][C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)=[N:35][C:31]=3[CH:30]=2)=[CH:49][CH:50]=1)(=[O:22])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 70696Trimethylsilyl isocyanateHCID 231451755-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Produkt 1

HCID 114089432-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

5 mg of dimethylaminopyridine and 0.029 ml of trimethylsilyl isocyanate were added to a methylene chloride (1 ml) solution of 17.1 mg of 5-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 162 (step 7), 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], and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure 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]
  7. additionthe resulting fraction was diluted with ethyl acetate
  8. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was evaporated away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7819c548dc1b40ea81bc958cbf8fcd01
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728025B2

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