Diisopropylethylamine → 2-Methyl-N-[1-methyl-3-(4-methylphenyl)-2-phenylpropyl]-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide

HRID 1160735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160735
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1)([CH3:6])[C:3]([OH:5])=O.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]([NH2:29])[CH3:28])=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:6][C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1)([CH3:1])[C:3]([NH:29][CH:27]([CH3:28])[CH:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=1)=[O:5]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 160983422-Methyl-2-(5-(trifluoromethyl)pyridin-2-yloxy)propanoic acidHCID 222706534-(4-Methylphenyl)-3-phenylbutan-2-amine

Produkt 1

HCID 222706002-Methyl-N-[1-methyl-3-(4-methylphenyl)-2-phenylpropyl]-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoic acid (Reference example 55, 250 mg, 1.04 mmol) and 4-(4-methylphenyl)-3-phenylbutan-2-amine (Reference example 102, 260 mg, 1.04 mmol, mixture of 4 isomers) in CH2Cl2 (5.5 mL) at RT was added diisopropylethylamine (272 μl, 1.56 mmol) followed by PyBOP (649 mg, 1.25 mmol) and the reaction mixture stirred overnight. The reaction was purified by loading the reaction mixture directly onto a silica gel column and eluting from 0-30% EtOAc/hexane to give the title compound as a mixture of 4 isomers. The diastereomers were separated by HPLC on a ZORBAX RxSi column eluting 97% hexane: 3% ethanol at 20 mL/min with retention times of:

Aufarbeitung

  1. customThe reaction was purified
  2. washeluting from 0-30% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e993a46de7eb4510afe70150f70692e3
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816534B2

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