Pyridine → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-cyclopropylsulphonylaminomethyl-benzamide

HRID 1846099Notes

Reaction equation

HRID 1846099 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][C:12]=2[Cl:19])=[CH:5][C:4]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)=[O:22].[CH:31]1([S:34](Cl)(=[O:36])=[O:35])[CH2:33][CH2:32]1.N1C=CC=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[C:15]([CH2:17][NH:18][S:34]([CH:31]3[CH2:33][CH2:32]3)(=[O:36])=[O:35])[CH:14]=[CH:13][C:12]=2[Cl:19])=[CH:5][C:4]=1[C:21]([NH:23][C:24]1[CH:25]=[CH:26][C:27]([Br:30])=[CH:28][CH:29]=1)=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chlorideHCID 67116388N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide

Product 1

HCID 52919730N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-cyclopropylsulphonylaminomethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 52.5 mg N-[4-methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide (0.10 mmol), 16.8 mg cyclopropylsulphonic acid chloride (0.12 mmol), 1.0 mL pyridine and 4.0 mL acetonitrile was stirred overnight, concentrated, dissolved in 3 mL DMF and purified by prep. HPLC.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in 3 mL DMF
  3. custompurified by prep

Sources & evidence

ORD record
ord-1a53da1ceabe421293ccd26d9db9fcd3
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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