Triethylamine → 2-(4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428715Notes

Reaction equation

HRID 1428715 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:17])[C:14]([OH:16])=O)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:18]1([CH3:36])[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=[C:26]([C:32]([F:35])([F:34])[F:33])[N:25]=2)[CH:19]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([CH3:17])[C:14]([NH:31][CH2:30][C:29]2[C:24]([C:20]3[CH:19]=[C:18]([CH3:36])[CH:23]=[CH:22][CH:21]=3)=[N:25][C:26]([C:32]([F:35])([F:33])[F:34])=[CH:27][CH:28]=2)=[O:16])=[CH:11][CH:12]=1)(=[O:3])=[O:4]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 708161912-(4-(Methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 715394732-(4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-(methylsulfonamidomethyl)phenyl)propanoic acid (60 mg, 0.233 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (62 mg, 0.233 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (67 mg, 0.349 mmol), 1-hydroxybenzotriazole (47 mg, 0.349 mmol) and triethylamine (0.08 mL, 0.582 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to obtain 2-(4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 4) (81 mg, 69%).

Workup

  1. washwashed with water 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-63fc189bfba74bd382137ac3642d5202
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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