Methyl triflate → (S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 131495Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6](=S)[C:5]=2[N:4]=1.FC(F)(F)S(OC)(=O)=O.[CH3:29][O:30][CH2:31][CH2:32][C@H:33]1[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1>>[CH3:29][O:30][CH2:31][CH2:32][C@@H:33]1[NH:34][CH2:35][CH2:36][N:37]([C:6]2[C:5]3[N:4]=[C:3]([C:2]([F:19])([F:18])[F:1])[S:12][C:11]=3[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=2)[CH2:38]1

Participants

Reactant 3

HCID 9526Methyl triflate

HCID 21093516HCID 21093516, compound

HCID 55287560(S)-2-(2-Methoxyethyl)piperazine

Product 1

HCID 135457486(S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Procedure

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).

Workup

customfollowed by purification
washeluting with a gradient of a 7% solution of 2M ammonia in methanol, in dichloromethane (0-100%)

Sources & evidence

ORD record: ord-375aeed6e25049b5b242c57f556ee7cd
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

Loading…