Hydrogen Peroxide → HCID 58338348, compound

HRID 1877503Notes

Reaction equation

HRID 1877503 reaction equation
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-].[K+].[K+].Cl.[CH3:40][N:41]1[CH:45]=[C:44]([CH2:46][CH2:47][NH2:48])[N:43]=[CH:42]1.[OH-:49].[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:49])=[C:2]([NH:48][CH2:47][CH2:46][C:44]6[N:43]=[CH:42][N:41]([CH3:40])[CH:45]=6)[CH:9]=5)[C:22]=4[CH:21]=[CH:20][CH:19]=3)[NH:27][C:26]=2[CH:28]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 16219661HCID 16219661, compoundHCID 583383582-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 58338348HCID 58338348, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 168.2 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, 165.8 mg of potassium carbonate, 517 mg of 2-(1-methyl-1H-imidazol-4-yl)ethylamine hydrochloride and 324 mg of triethylamine in 1.7 ml of dimethyl sulphoxide, in a microwave for 1 hour and 30 minutes at 115° C. 0.76 ml of a 1M aqueous solution of sodium hydroxide, 0.735 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 10 g of silica gel, elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume), 34 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-y0-9H-carbazol-9-yl]-2-[(1-methyl-1H-imidazol-4-yl)ethylamino]benzamide are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. customAfter treatment as in stage 3 of Example 3, and then purification by flash chromatography
  3. washon 10 g of silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and methanol (95/5 by volume), 34 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-y0-9H-carbazol-9-yl]-2-[(1-methyl-1H-imidazol-4-yl)ethylamino]benzamide
  5. customare thus obtained in the form of a white solid

Sources & evidence

ORD record
ord-6c97267235244752bd01bced0d5a8f38
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

Loading…