Methanesulfonyl chloride → HCID 71539430, compound

HRID 1428756Notes

Reaction equation

HRID 1428756 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])=[CH:5][C:4]=1[O:32][CH3:33].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>N1C=CC=CC=1.ClCCl>[CH3:33][O:32][C:4]1[CH:5]=[C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)=[O:11])[CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][S:35]([CH3:34])(=[O:37])=[O:36]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86680221HCID 86680221, compound

Product 1

HCID 71539430HCID 71539430, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(aminomethyl)-3-methoxyphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (151 mg, 0.33 mmol) in pyridine, cooled to 0° C., were added methanesulfonyl chloride (151 mg). The resulting reaction mixture was stirred for 15 h at room temperature. The mixture dissolved in dichloromethane and washed with 1N HCl. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Methoxy-4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 78) (38 mg) was obtained as 22% yield.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-a2808897121243f380b80daf755a2551
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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