Réaction #5044

ord-cddc616ecddf4bfb83a9be619ed5fcde

Équation de réaction

Cc1ccc(Br)nn1
6-methyl-3-bromopyridazine
CCN(C(C)C)C(C)C
DIPEA
OC1CCNCC1
4-hydroxypiperidine
CCCc1ccc(N2CCC(O)CC2)nn1
Formula IV
CCCc1ccc(N2CCC(O)CC2)nn1
6-n-propyl-3-(4-hydroxy-1-piperidinyl)pyridazine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureheated to 120° for 16 hours

Mode opératoire

Following a procedure similar to that of Example 3, 81 millimoles of 6-methyl-3-bromopyridazine was combined with 16 mL DIPEA and 163 mmoles of 4-hydroxypiperidine and heated to 120° for 16 hours to obtain 6-methyl-3-(4-hydroxy-1-piperdinyl)pyridazine (Formula IV: Y=bond, R=CH3) in 24% yield. 6.8 Mmols of the latter and 7.4 mmoles of 2-methyl-5-(4-hydroxy-3,5-dimethyl phenyl)-2H-tetrazole (Formula III: R2 =R3 =R4 =CH3) were reacted with equimolar amounts of DEAD and TPP essentially as described above in Example 1c. Recrystallization from methanol gave a 74% yield of the compound of Formula I (R1 =R2 =R3 =R4 =CH3, Y=bond), m.p. 188°-189° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05242924uspto-grants-1993_09