Hydrogen Peroxide → HCID 58338299, compound

HRID 1877506Notes

Reaction equation

HRID 1877506 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[CH:24]=[N:25][C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)[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+].[NH2:39][CH2:40][C:41]1([OH:44])[CH2:43][CH2:42]1.[OH-].[Na+].OO>CS(C)=O.C(O)C>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[C:23]([C:18]2[C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([C:8]4[CH:7]=[CH:6][C:3]([C:4]([NH2:5])=[O:34])=[C:2]([NH:39][CH2:40][C:41]5([OH:44])[CH2:43][CH2:42]5)[CH:9]=4)[C:22]=3[CH:21]=[CH:20][CH:19]=2)[CH:24]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 126096231-(Aminomethyl)cyclopropan-1-olHCID 673078612-Fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 58338299HCID 58338299, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 165.4 mg of 2-fluoro-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzonitrile, obtained according to stage 2 of Example 3, 165.8 mg of potassium carbonate and 279 mg of 1-(aminomethyl)cyclopropan-1-ol 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 silica gel, elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume), 11 mg of 4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]-2-[(1-hydroxycyclopropan-1-yl)methylamino]benzamide are thus obtained in the form of a pale yellow powder, the characteristics of which are as follows:

Workup

  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 methanol (95/5 by volume), 11 mg of 4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]-2-[(1-hydroxycyclopropan-1-yl)methylamino]benzamide
  5. customare thus obtained in the form of a pale yellow powder

Sources & evidence

ORD record
ord-bf15cb8127414df2800c9be90c7601f0
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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