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

HRID 1428772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428772
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=O)=[CH:10][C:9]=1[F:19])(=[O:5])=[O:4])[CH3:2].[C:20]1([CH3:38])[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=[C:28]([C:34]([F:37])([F:36])[F:35])[N:27]=2)[CH:21]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCOCC1>[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([NH:33][CH2:32][C:31]2[C:26]([C:22]3[CH:21]=[C:20]([CH3:38])[CH:25]=[CH:24][CH:23]=3)=[N:27][C:28]([C:34]([F:37])([F:35])[F:36])=[CH:29][CH:30]=2)=[O:17])=[CH:10][C:9]=1[F:19])(=[O:4])=[O:5])[CH3:2]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 708165692-(4-(Ethylsulfonamidomethyl)-3-fluorophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Produkt 1

HCID 715393842-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-(4-(Ethylsulfonamidomethyl)-3-fluorophenyl)propanoic acid (60 mg, 0.207 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (61 mg, 0.228 mmol) was dissolved and mixed in 1,4-dioxane, followed by addition of N-hydroxybenzotriazole (42 mg, 0.311 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (60 mg, 0.311 mmol) and triethylamine (0.07 mL, 0.518 mmol). The reaction mixture was stirred for overnight and then quenched by water and extracted with ethyl acetate. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 83) in pure form (52 mg, 47%).

Aufarbeitung

  1. customquenched by water
  2. extractionextracted with ethyl acetate
  3. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-96a9d30b0de84839afc976e24913a79a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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