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Ethyl Acetate → [4-(6-Chloro-quinolin-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

HRID 33190
Notes
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Reaction equation

HRID 33190 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH:7]=[CH:6]2.[CH3:19][S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:32][C@@H:33]([CH3:38])[C:34]([F:37])([F:36])[F:35])=[C:27]([CH:31]=1)[C:28](O)=[O:29])(=[O:22])=[O:21].C(OCC)(=O)C>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([N:13]1[CH2:14][CH2:15][N:16]([C:28]([C:27]3[CH:31]=[C:23]([S:20]([CH3:19])(=[O:21])=[O:22])[CH:24]=[CH:25][C:26]=3[O:32][C@@H:33]([CH3:38])[C:34]([F:36])([F:37])[F:35])=[O:29])[CH2:17][CH2:18]1)[CH:7]=[CH:6]2
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acidHCID 688966846-Chloro-2-piperazin-1-yl-quinoline hydrochloride

Product 1

HCID 58970540[4-(6-Chloro-quinolin-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

Prepared in analogy to example 1.1 b) from 6-chloro-2-piperazin-1-yl-quinoline hydrochloride (Example 1.20b) and 5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example 2.7) in acetonitrile. Chromatography (SiO2; ethyl acetate) yields the title compound as a colorless solid.

Sources & evidence

ORD record
ord-93387aadda324c1a93279990476aedca
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429585B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes