p-Toluenesulfonic acid monohydrate → HCID 59210411, compound

HRID 2243243Notes

Reaction equation

HRID 2243243 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:11]([NH:13][C:14]([CH3:19])([CH3:18])[CH2:15][S:16][CH3:17])=[O:12].[CH3:20][C:21]1[CH:27]=[C:26]([CH:28]([N:30]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[N:31]2)[CH3:29])[CH:25]=[CH:24][C:22]=1[NH2:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:18][C:14]([NH:13][C:11](=[O:12])[C:3]1[C:4](=[CH:8][CH:9]=[CH:10][C:2]=1[I:1])[C:5]([NH:23][C:22]1[CH:24]=[CH:25][C:26]([CH:28]([N:30]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[N:31]2)[CH3:29])=[CH:27][C:21]=1[CH3:20])=[O:7])([CH3:19])[CH2:15][S:16][CH3:17]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59210381HCID 59210381, compoundHCID 59210407HCID 59210407, compound

Product 1

HCID 59210411HCID 59210411, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Iodo-N-(1,1-dimethyl-2-methylsulfanyl-ethyl)-phthalamic acid (0.39 g) and N-(3-dimethylaminopropyl)-N1-ethylcarbonyl diimidazole hydrochloride (0.19 g) were stirred in dichloromethane (10 ml) at room temperature for 30 minutes. Then, 2-methyl-4-[1-(3-trifluoromethyl-1H-pyrazol-1-yl)-ethyl]-aniline (0.30 g) and p-toluenesulphonic acid monohydrate (0.02 g) were added thereto and the mixture was stirred at room temperature for 3 hours. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain N2-(1,1-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-N1-{2-methyl-4-[1-(3-trifluoromethyl-1H-pyrazol-1-yl)-ethyl]-phenyl}-phthalamide (0.38 g) (compound No. 558). mp. 79-86° C.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-01ee5e3e5a39486db5b4b3d98b75c989
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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