Pyridine → HCID 178483252, compound

HRID 2109027Notes

Reaction equation

HRID 2109027 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:31]=[CH:30][C:8]([NH:9]/[C:10](=[C:19]2\[C:20](=[O:29])[NH:21][C:22]3[C:27]\2=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)/[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].N1C=CC=CC=1.[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.[OH-].[Na+]>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:9]/[C:10](=[C:19]2\[C:20](=[O:29])[NH:21][C:22]3[C:27]\2=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)/[C:11]2[CH:12]=[CH:13][C:14]([CH2:17][NH:18][S:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)(=[O:46])=[O:45])=[CH:15][CH:16]=2)=[CH:30][CH:31]=1)[CH3:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178483251HCID 178483251, compound

Product 1

HCID 178483252HCID 178483252, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

100 mg of 3-Z-[1-(4-dimethylaminomethyl-anilino)-1-(4-aminomethyl-phenyl)-methylene]-6-chloro-2-indolinone (educt 14.0) are dissolved in 5 ml methylene chloride and at 0° C. 5 ml of pyridine and 45 μl of benzenesulphonylchloride are added. The mixture is stirred for 10 minutes at 0° C. and then for 2 hours at ambient temperature. After this time the solvent is eliminated, the residue is suspended in 1N sodium hydroxide solution, suction filtered and washed with a little water. The product is dried at 100° C.

Workup

  1. waitfor 2 hours at ambient temperature
  2. filtrationsuction filtered
  3. washwashed with a little water
  4. customThe product is dried at 100° C.

Sources & evidence

ORD record
ord-e276a453d0a94fe68c66ce29b6dfb411
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

Loading…