5-Bromo-2-chloropyrimidine → 4-(1-(5-Bromopyrimidin-2-yl)piperidin-4-yloxy)-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazine-3-carbonitrile

HRID 386572

Reaktionsgleichung

Reaktionsgleichung von HRID 386572
ClC1N=CC(C2CC2)=CN=1.Cl.ClC1C=C(N2C(=O)C=C(OC3CCNCC3)C(C#N)=N2)C=CC=1Cl.[Br:36][C:37]1[CH:38]=[N:39][C:40](Cl)=[N:41][CH:42]=1.Cl.[C:45]([C:47]1[CH:52]=[CH:51][C:50]([N:53]2[C:58](=[O:59])[CH:57]=[C:56]([O:60][CH:61]3[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]3)[C:55]([C:67]#[N:68])=[N:54]2)=[CH:49][C:48]=1[F:69])#[N:46]>>[Br:36][C:37]1[CH:38]=[N:39][C:40]([N:64]2[CH2:65][CH2:66][CH:61]([O:60][C:56]3[C:55]([C:67]#[N:68])=[N:54][N:53]([C:50]4[CH:51]=[CH:52][C:47]([C:45]#[N:46])=[C:48]([F:69])[CH:49]=4)[C:58](=[O:59])[CH:57]=3)[CH2:62][CH2:63]2)=[N:41][CH:42]=1

Komponenten

5

Edukt 4

HCID 6066655-Bromo-2-chloropyrimidineHCID 468640872-Chloro-5-cyclopropylpyrimidineHCID 674465361-(3,4-dichlorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HClHCID 674470261-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt

Produkt 1

HCID 446210894-(1-(5-Bromopyrimidin-2-yl)piperidin-4-yloxy)-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazine-3-carbonitrileAusbeute 89 %

Versuchsvorschrift

Example 41 was prepared in 89% yield according to procedures described in Example 21 substituting 2-chloro-5-cyclopropylpyrimidine and 1-(3,4-dichlorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl for 5-bromo-2-chloropyrimidine and 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt. 1H NMR (400 MHz, CDCl3) δ ppm 0 1.90-2.01 (m, 2H) 2.01-2.19 (m, 2H) 3.78-3.91 (m, 2H) 3.99-4.19 (m, 2H) 4.52-4.93 (m, 1H) 6.32 (s, 1H) 7.60-7.71 (m, 2H) 7.71-7.82 (m, 1H) 8.31 (s, 2H). MS (ESI) 497 (M+H).

Aufarbeitung

  1. customExample 41 was prepared in 89% yield

Quellen und Nachweise

ORD-Eintrag
ord-01992edc3a784e3fb10a3afa00dd5ed6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372837B2

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