Methanesulfonyl chloride → HCID 71539337, compound

HRID 1428808Notes

Reaction equation

HRID 1428808 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[CH3:32].[CH3:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1.C(OC(=O)C)C>[CH3:32][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:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:11])[CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][S:34]([CH3:33])(=[O:36])=[O:35]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86680236HCID 86680236, compound

Product 1

HCID 71539337HCID 71539337, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-(aminomethyl)-3-methylphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (83 mg, 0.19 mmol) in pyridine was added methanesulfonyl chloride (0.02 mL, 0.24 mmol) The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate and washed with 1N HCl and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Methyl-4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 97) (60 mg) was obtained as 61% yield.

Workup

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

Sources & evidence

ORD record
ord-03af2068d7c1431bbb52e82614de36f7
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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