Reaktion #1132989

ord-3591476f8919483995d2097da672d051

Reaktionsgleichung

Cc1cc(C2CCN(C(=O)[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1
product
Cc1cc(C2CCN(C(=O)[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1
tert-butyl (3S,4R)-3-({4-[1-(3-chloro-4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]piperidin-1-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidine-1-carboxylate
O=C(O)C(F)(F)F
TFA
→
Cc1cc(C2CCN(C(=O)[C@@H]3CNC[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1.O=C(O)C(F)(F)F
title compound
Cc1cc(C2CCN(C(=O)[C@@H]3CNC[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1.O=C(O)C(F)(F)F
[4-[2-(3-chloro-4-fluoro-phenyl)-5-methyl-pyrazol-3-yl]-1-piperidyl]-[(3S,4R)-4-(2,4-difluorophenyl)pyrrolidin-3-yl]methanone trifluoroacetate salt

Edukte

Cc1cc(C2CCN(C(=O)[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1
product
Cc1cc(C2CCN(C(=O)[C@@H]3CN(C(=O)OC(C)(C)C)C[C@H]3c3ccc(F)cc3F)CC2)n(-c2ccc(F)c(Cl)c2)n1
tert-butyl (3S,4R)-3-({4-[1-(3-chloro-4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]piperidin-1-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidine-1-carboxylate
O=C(O)C(F)(F)F
TFA

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated
  2. 2
    Sonstigepurified by RP-HPLC (C-18, acetonitrile, H2O, 10 to 100% over 12 min, 0.05% TFA)

Vorschrift

The product from step A was dissolved in CH2Cl2 (5 mL) and treated with TFA (2.5 mL). The mixture was stirred at rt for 6 h, concentrated and purified by RP-HPLC (C-18, acetonitrile, H2O, 10 to 100% over 12 min, 0.05% TFA) to afford the title compound. HPLC/MS: 503.2/505.2 (M+1); Rt=1.62 min (LC4).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08569299B2uspto-grants-2013_10