2-Chloro-5-propylpyrimidine → 1-(4-Cyano-3-fluorophenyl)-6-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile

HRID 386571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386571
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][N:3]=1.Cl.ClC1C=C(N2C(=O)C=C(OC3CCNCC3)C(C#N)=N2)C=CC=1Cl.ClC1N=CC(CCC)=CN=1.Cl.[C:47]([C:49]1[CH:54]=[CH:53][C:52]([N:55]2[C:60](=[O:61])[CH:59]=[C:58]([O:62][CH:63]3[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]3)[C:57]([C:69]#[N:70])=[N:56]2)=[CH:51][C:50]=1[F:71])#[N:48]>>[C:47]([C:49]1[CH:54]=[CH:53][C:52]([N:55]2[C:60](=[O:61])[CH:59]=[C:58]([O:62][CH:63]3[CH2:64][CH2:65][N:66]([C:2]4[N:3]=[CH:4][C:5]([CH2:8][CH2:10][CH3:9])=[CH:6][N:7]=4)[CH2:67][CH2:68]3)[C:57]([C:69]#[N:70])=[N:56]2)=[CH:51][C:50]=1[F:71])#[N:48]

Komponenten

5

Edukt 4

HCID 27357842-Chloro-5-propylpyrimidineHCID 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 446210461-(4-Cyano-3-fluorophenyl)-6-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrileAusbeute 56 %

Versuchsvorschrift

Example 38 was prepared in 56% 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 2-chloro-5-propylpyrimidine 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 0.93 (t, J=7.25 Hz, 3H) 1.48-1.67 (m, 2H) 1.82-2.01 (m, 2H) 2.01-2.17 (m, 2H) 2.41 (t, J=7.69 Hz, 2H) 3.60-3.91 (m, 2H) 3.98-4.27 (m, 2H) 4.48-4.87 (m, 1H) 6.32 (s, 1H) 7.52-7.70 (m, 2H) 7.70-7.81 (m, 1H) 8.17 (s, 2H). MS (ESI) 460 (M+H).

Aufarbeitung

  1. customExample 38 was prepared in 56% yield

Quellen und Nachweise

ORD-Eintrag
ord-debc44ffba83433eb43c9493a84f9224
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372837B2

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