(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone → [2-(3,5-Bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidin-5-yl]-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

HRID 1692417

Reaktionsgleichung

Reaktionsgleichung von HRID 1692417
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.[F:47][C:48]([F:81])([F:80])[C:49]1[CH:50]=[C:51]([C:59]2[N:64]=[C:63]([CH3:65])[C:62]([C:66](N3CCC(N4CCCC4)CC3)=[O:67])=[C:61]([CH3:79])[N:60]=2)[CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1.[N:82]1([CH:97]2[CH2:102][CH2:101][NH:100][CH2:99][CH2:98]2)[CH2:87][CH2:86][CH:85]([O:88]C(=O)C2C=CC=CC=2)[CH2:84][CH2:83]1>>[F:81][C:48]([F:47])([F:80])[C:49]1[CH:50]=[C:51]([C:59]2[N:60]=[C:61]([CH3:79])[C:62]([C:66]([N:100]3[CH2:99][CH2:98][CH:97]([N:82]4[CH2:83][CH2:84][CH:85]([OH:88])[CH2:86][CH2:87]4)[CH2:102][CH2:101]3)=[O:67])=[C:63]([CH3:65])[N:64]=2)[CH:52]=[C:53]([C:55]([F:56])([F:58])[F:57])[CH:54]=1

Komponenten

5

Edukt 4

HCID 44473778(4-Bromo-2,6-dimethyl-phenyl)-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanoneHCID 57580536[2-(3,5-Bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidin-5-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 66901535Benzoic acid [1,4']bipiperidinyl-4-yl esterHCID 66901599(4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Produkt 1

HCID 57580557[2-(3,5-Bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidin-5-yl]-(4-hydroxy-[1,4']bipiperidinyl-1'-yl)-methanone

Versuchsvorschrift

In analogy to the procedures described for intermediate 1 and for intermediate 4 B, 2-(3,5-bis-trifluoromethyl-phenyl)-4,6-dimethyl-pyrimidine-5-carboxylic acid (example 15) was converted into its acid chloride, reacted with benzoic acid [1,4′]bipiperidinyl-4-yl ester (example 22) and subsequently saponified to give the title compound as colorless solid. MS: 531.1 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-2a98c80825eb4e9e99a6bab6a7e0abfe
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153805B2

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