Triethylamine → N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

HRID 1428725Notes

Reaction equation

HRID 1428725 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH:19]1([C:22]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[C:25]([CH2:35][NH2:36])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCOCC1.C(OC(=O)C)C>[CH:19]1([C:22]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[C:25]([CH2:35][NH:36][C:15](=[O:17])[CH:14]([C:4]3[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12])=[C:2]([F:1])[CH:3]=3)[CH3:18])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680211(6-Cyclopropyl-2-m-tolylpyridin-3-yl)methanamine

Product 1

HCID 71539635N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamideYield 52%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (41 mg, 0.148 mmol) and (6-cyclopropyl-2-m-tolylpyridin-3-yl)methanamine (35 mg, 0.148 mmol) in dioxane were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (43 mg, 0.222 mmol), 1-hydroxybenzotriazole (30 mg, 0.222 mmol) and triethylamine (0.05 mL, 0.37 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethylacetate 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. N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 20) (38 mg) was obtained as 52% yield.

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-5bdc4ced22f742bfbc741e0ffdb06e27
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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