Hydrochloric Acid → [6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-trifluoromethanesulfonyl-piperazin-1-yl)-methanone

HRID 1786458Notes

Reaction equation

HRID 1786458 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11](O)=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]1.Cl.[F:25][C:26]([F:37])([F:36])[S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28].FC(F)(F)S(Cl)(=O)=O.N1(C(OC(C)(C)C)=O)CCNCC1>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:33]3[CH2:32][CH2:31][N:30]([S:27]([C:26]([F:36])([F:37])[F:25])(=[O:28])=[O:29])[CH2:35][CH2:34]3)=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:22])[CH3:23])[CH2:17][CH2:16]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79000Trifluoromethanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 186908331-((Trifluoromethyl)sulfonyl)piperazineHCID 670179316-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid

Product 1

HCID 68565282[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-trifluoromethanesulfonyl-piperazin-1-yl)-methanoneYield 48%

Procedure

The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid; hydrochloride (example 1, intermediate a) and 1-trifluoromethanesulfonyl-piperazine (prepared in analogy to International Patent Application Publ. No. WO 2003/064413 by using trifluoromethanesulfonyl chloride and tert-butyl 1-piperazinecarboxylate) to afford the title compound as a yellow solid (48%).

Sources & evidence

ORD record
ord-3ebb0e6b7e434129bfef22e8e0b9d4cf
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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