Methanesulfonyl chloride → HCID 71539429, compound

HRID 1428748Notes

Reaction equation

HRID 1428748 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[Cl:32].[CH3:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1.ClCCl>[Cl: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 86680218HCID 86680218, compound

Product 1

HCID 71539429HCID 71539429, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(aminomethyl)-3-chlorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (90 mg, 0.195 mmol) in pyridine, cooled to 0° C., were added methanesulfonyl chloride (90 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-Chloro-4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 77) (87 mg) was obtained as 83% yield. 1H NMR (300 MHz, CDCl3) 7.77 (d, 1H, J=8.04 Hz, Ar), 7.58 (d, 1H J=8.07 Hz, Ar), 7.39 (d, 1H, J=7.86 Hz, Ar), 7.28 (m, 4H, Ar), 7.13 (m, 2H, Ar), 5.59 (t, 1H, NH), 4.82 (t, 1H, NH), 4.47 (d, 2H, J=6.03 Hz, CH2), 4.37 (d, 2H, J=6.39, CH2), 3.44 (q, 1H, CH), 2.88 (s, 3H, mesyl), 2.38 (s, 3H, methyl), 1.44 (d, 3H, J=7.14 Hz, CH3)

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-8efbf34c22b44619bb2e418779d233b8
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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