151140-64-6Relevant articles and documents
An efficient Fischer indole synthesis of avitriptan, a potent 5-HT(1D) receptor agonist
Brodfuehrer,Chen,Sattelberg T.R.,Smith,Reddy,Stark,Quinlan,Reid
, p. 9192 - 9202 (1997)
An efficient synthesis of antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaler-aldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5- chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.
Antimigraine 4-pyrimidinyl and pyridinyl derivatives of indol-3yl-alkylpiperazines
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, (2008/06/13)
A series of novel alkoxypyridin-4-yl and alkoxypyrimidin-4-yl derivatives of indol-3-ylalkylpiperazines of Formula I are intended to be useful agents STR1 for alleviation of vascular headache on the basis of their potent affinity and agonist activity at 5-HT1D binding sites.
