Acetonitrile → 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide

HRID 1790716

Reaktionsgleichung

Reaktionsgleichung von HRID 1790716
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:33]=[CH:32][C:17]3[N:18]([CH3:31])[C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[CH:23]=4)=[N:20][C:16]=3[CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:6].C([O-])([O-])=O.[K+].[K+].C(#N)C.[C:43]1([CH2:49][S:50](Cl)(=[O:52])=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O>[C:43]1([CH2:49][S:50]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:33]=[CH:32][C:17]4[N:18]([CH3:31])[C:19]([NH:21][C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[CH:23]=5)=[N:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:6])(=[O:52])=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 210373234-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzo-imidazol-5-yloxy]-pyridine-2-carboxylic acid (2-amino-ethyl)-amide

Produkt 1

HCID 220412414-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a mixture containing 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-amino-ethyl)-amide (1 eq) (prepared using previously described example 3), K2CO3 (5 eq), (0.2 M in a 5:1 mixture of acetonitrile and water) were added α-toluenesulfonyl chloride (1 eq) via syringe. The resulting heterogeneous mixture was allowed to stir for 1 hour at room temperature. The mixture was then diluted with water and extracted with dichloromethane. The organics were washed with water and a saturated solution of sodium chloride, dried with sodium sulfate and concentrated in vacuo to viscous oil. Purification by chromatography yielded 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-phenylmethanesulfonylamino-ethyl)-amide. MS: MH+599

Aufarbeitung

  1. customprepared
  2. extractionextracted with dichloromethane
  3. washThe organics were washed with water
  4. dry with materiala saturated solution of sodium chloride, dried with sodium sulfate
  5. concentrationconcentrated in vacuo to viscous oil
  6. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-33389ec7e72c4df3b9b8deccba4fd745
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071216B2

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