Réaction #218677

ord-375aeed6e25049b5b242c57f556ee7cd

Équation de réaction

FC(F)(F)c1nc2c(s1)Nc1ccccc1NC2=S
2-trifluoromethyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo[f]azulene-10-thione
COS(=O)(=O)C(F)(F)F
methyl trifluoromethanesulfonate
COCC[C@H]1CNCCN1
2-(S)-(2-methoxy-ethyl)-piperazine
COCC[C@H]1CN(C2=Nc3ccccc3Nc3sc(C(F)(F)F)nc32)CCN1
title compound
COCC[C@H]1CN(C2=Nc3ccccc3Nc3sc(C(F)(F)F)nc32)CCN1
(S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrefollowed by purification
  2. 2
    Lavageeluting with a gradient of a 7% solution of 2M ammonia in methanol, in dichloromethane (0-100%)

Mode opératoire

Using the method of Example 305, using 2-trifluoromethyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo[f]azulene-10-thione and methyl trifluoromethanesulfonate, and 2-(S)-(2-methoxy-ethyl)-piperazine, followed by purification, eluting with a gradient of a 7% solution of 2M ammonia in methanol, in dichloromethane (0-100%), gives the title compound: mass spectrum (APCI, m/e): 412 (M+1); NMR (1H, 300 MHz, DMSO-d6): δ 8.71 (br. s, 1H), 8.60 (s, 1H), 6.93 (m, 3H), 6.71 (m, 1H), 4.07 (br. m, 2H), 3.46-3.29 (m, 4H), 3.29-3.06 (m, 5H), 2.99 (m, 1H), 2.48 (m, 2H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07384934B2uspto-grants-2008_06