Hydrogen Peroxide → 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(3-hydroxy-3-methylbutylamino)benzamide

HRID 1877472

Reaktionsgleichung

Reaktionsgleichung von HRID 1877472
F[C:2]1[CH:9]=[C:8]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([C:23]4[NH:27][C:26]5[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:25]=5[N:24]=4)[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-:34].[K+].[K+].Cl.[NH2:40][CH2:41][CH2:42][C:43]([CH3:46])([OH:45])[CH3:44].[OH-].[Na+].OO>CS(C)=O.C(O)C.C(N(CC)CC)C>[F:32][C:29]1[CH:30]=[CH:31][C:25]2[N:24]=[C:23]([C:18]3[C:17]4[C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]([C:8]5[CH:7]=[CH:6][C:3]([C:4]([NH2:5])=[O:34])=[C:2]([NH:40][CH2:41][CH2:42][C:43]([OH:45])([CH3:46])[CH3:44])[CH:9]=5)[C:22]=4[CH:21]=[CH:20][CH:19]=3)[NH:27][C:26]=2[CH:28]=1

Komponenten

9

Edukt 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 426145604-Amino-2-methylbutan-2-ol hydrochlorideHCID 583383582-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile

Produkt 1

HCID 583381844-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(3-hydroxy-3-methylbutylamino)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

The process is carried out as in stage 3 of Example 3, but using 155.6 mg of 2-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]benzonitrile, obtained according to stage 2 of Example 3, 153.4 mg of potassium carbonate, 1.033 g of 4-amino-2-methylbutan-2-ol hydrochloride and 0.749 g of triethylamine in 2 ml of dimethyl sulphoxide. 0.703 ml of a 1M aqueous solution of sodium hydroxide, 0.681 ml of a 30% aqueous solution of hydrogen peroxide and 4 ml of ethanol are then added to the reaction medium. After treatment as in stage 3 of Example 3, and then purification by flash chromatography on silica gel, elution being carried out with a mixture of dichloromethane and ethanol (95/5 by volume), followed by crystallization from 5 ml of ethyl acetate, 185 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(3-hydroxy-3-methylbutylamino)benzamide are thus obtained in the form of a beige solid, the characteristics of which are the following:

Aufarbeitung

  1. customobtained
  2. customAfter treatment as in stage 3 of Example 3, and then purification by flash chromatography
  3. washon silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ethanol (95/5 by volume)
  5. customfollowed by crystallization from 5 ml of ethyl acetate, 185 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(3-hydroxy-3-methylbutylamino)benzamide
  6. customare thus obtained in the form of a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-5c7f32542a37442abc1f64c75f95a21b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

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