Triethylamine → Methyl 3-(4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionoate

HRID 1669254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669254
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([O:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:41][O:42][C:43](=[O:47])[CH2:44][CH2:45][NH2:46].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([O:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([NH:46][CH2:45][CH2:44][C:43]([O:42][CH3:41])=[O:47])=[O:28])=[CH:30][CH:31]=3)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 192794Methyl beta-alanateHCID 673422064-{1-[6-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid

Produkt 1

HCID 67153427Methyl 3-(4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionoateAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid (230 mg, 0.5 mmol) in methylene chloride (5 mL) are added triethyl amine (0.21 mL, 1.51 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (210.5 mg, 1.51 mmol) and EDCI (290 mg, 1.51 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight, loaded on silica gel, eluted with eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving methyl 3-(4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionoate (260 mg).

Aufarbeitung

  1. washeluted
  2. washwith eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b5815f1b83e840e19459e773cfb9fa20
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989457B2

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