(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone → benzoic acid (S)-1-{1-[4,6-dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

HRID 1692407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692407
BrC1C=C(C)C(C(N2CCC(N3CCCC3)CC2)=O)=C(C)C=1.BrC1C=C(C)C(C(N2CCC(N3CCC[C@H]3CO)CC2)=O)=C(C)C=1.[CH3:47][C:48]1[C:53]([C:54](O)=[O:55])=[C:52]([CH3:57])[N:51]=[C:50]([C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=2)[N:49]=1.[NH:68]1[CH2:73][CH2:72][CH:71]([N:74]2[CH2:78][CH2:77][CH2:76][C@H:75]2[CH2:79][O:80][C:81](=[O:88])[C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH2:70][CH2:69]1>>[CH3:57][C:52]1[C:53]([C:54]([N:68]2[CH2:73][CH2:72][CH:71]([N:74]3[CH2:78][CH2:77][CH2:76][C@H:75]3[CH2:79][O:80][C:81](=[O:88])[C:82]3[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=3)[CH2:70][CH2:69]2)=[O:55])=[C:48]([CH3:47])[N:49]=[C:50]([C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=2)[N:51]=1

Komponenten

5

Edukt 4

HCID 44473778(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanoneHCID 627447164,6-Dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid2×HCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester2×HCID 66901599(4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Produkt 1

HCID 66901643benzoic acid (S)-1-{1-[4,6-dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

Versuchsvorschrift

In analogy to the procedures described for intermediate 1 and for intermediate 4 B), 4,6-dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (intermediate 5) was converted into its acid chloride and subsequently reacted with benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester (intermediate 3) to give benzoic acid (S)-1-{1-[4,6-dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester, which was subsequently saponified to give the title compound as colorless solid. MS: 463.2 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-6946dfe4ea0c41c9b9bc1e29a224b1b6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153805B2

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