Hydrogen Peroxide → 2-[(pyridin-2-ylmethyl)amino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide

HRID 1877488Notes

Reaction equation

HRID 1877488 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-].[K+].[K+].[NH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1.[OH-:47].[Na+].OO>CS(C)=O.C(O)C>[N:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[CH2:40][NH:39][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]([NH2:5])=[O:47]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 673078612-Fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile

Product 1

HCID 583382872-[(pyridin-2-ylmethyl)amino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The process is carried out as in stage 3 of Example 3, but using 150 mg of 2-fluoro-4-[4-(quinolin-3-yl)carbazol-9-yl]benzonitrile, obtained according to stage 1 of Example 32, 150.5 mg of potassium carbonate and 0.785 g of 2-(aminomethyl)pyridine in 2 ml of dimethyl sulphoxide. 0.69 ml of a 1M aqueous solution of sodium hydroxide, 0.667 ml of a 30% aqueous solution of hydrogen peroxide and 3 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 ammonia as a 7M solution in methanol (from 90/10 to 80/20 by volume), followed by crystallization from 1 ml of ethyl acetate and 3 ml of diisopropyl ether, 95 mg of 2-[(pyridin-2-ylmethyl)amino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide are thus obtained in the form of a beige 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 silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ammonia as a 7M solution in methanol (from 90/10 to 80/20 by volume)
  5. customfollowed by crystallization from 1 ml of ethyl acetate and 3 ml of diisopropyl ether, 95 mg of 2-[(pyridin-2-ylmethyl)amino]-4-[4-(quinolin-3-yl)-9H-carbazol-9-yl]benzamide
  6. customare thus obtained in the form of a beige solid

Sources & evidence

ORD record
ord-32e890c7ec3f4268870dc6e808444587
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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