Trifluoroacetic acid → [1-((S)-2-Amino-propyl)-6-chloro-1H-indol-3-yl]-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanone

HRID 505186Notes

Reaction equation

HRID 505186 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(OC([NH:33][C@@H:34]([CH3:41])[CH2:35]OS(C)(=O)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH2:33][C@@H:34]([CH3:41])[CH2:35][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:15][CH2:14]2)=[O:12])=[CH:7]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterHCID 16061731(6-Chloro-1H-indol-3-yl)[4-(2-fluorophenyl)piperazin-1-yl]methanone

Product 1

HCID 46898555[1-((S)-2-Amino-propyl)-6-chloro-1H-indol-3-yl]-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanone

Procedure

Following general procedure II, the alkylation of (6-chloro-1H-indol-3-yl)-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanone (preparation described herein), with methanesulfonic acid (S)-2-tert-butoxycarbonylamino-propyl ester (described in WO 2005100321) gave, after treatment with TFA and subsequent neutralization, the title compound.

Workup

  1. customgave

Sources & evidence

ORD record
ord-78c0ad3199194e05b5f46bc3ed449cab
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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