Trifluoroacetic acid → HCID 68282623, Verbindung

HRID 1473154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473154
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][CH2:18][C:19]2[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][N:22]=[C:21]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([CH:36]4[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]4)=[CH:32][CH:31]=3)[N:20]=2)[CH:12]=1)(=[O:10])[NH2:9]>C(Cl)Cl>[NH:39]1[CH2:38][CH2:37][CH:36]([C:33]2[CH:34]=[CH:35][C:30]([NH:29][C:21]3[N:20]=[C:19]([CH2:18][CH2:17][C:13]4[CH:12]=[C:11]([CH:16]=[CH:15][N:14]=4)[C:8]([NH2:9])=[O:10])[C:24]([C:25]([F:28])([F:26])[F:27])=[CH:23][N:22]=3)=[CH:31][CH:32]=2)[CH2:41][CH2:40]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71209333HCID 71209333, Verbindung

Produkt 1

HCID 68282623HCID 68282623, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (100 μL, 0.131 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(4-carbamoylpyridin-2-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I130) (50 mg, 88 μmol) in DCM (4 mL) and the resulting mixture was stirred for 1 hour at room temperature. The volatiles were evaporated under reduced pressure and the residue purified by chromatography (SiO2, 0-50% MeOH/DCM) to give the title compound (I131) (28 mg, 68%) as a colourless solid; 1H NMR (400 MHz, d4-MeOD) δ 8.55 (d, J=5.2 Hz, 1H), 8.49 (s, 1H), 7.74 (s, 1H), 7.61 (dd, J=5.2, 1.3 Hz, 1H), 7.53 (d, J=8.3 Hz, 2H), 7.17 (d, J=8.5 Hz, 2H), 3.46 (d, J=12.7 Hz, 2H), 3.37 (t, J=7.0 Hz, 2H), 3.27 (dt, J=3.2, 1.6 Hz, 5H), 3.18-3.04 (m, 2H), 2.83 (ddd, J=12.1, 8.7, 3.6 Hz, 1H), 2.03 (d, J=13.8 Hz, 2H), 1.88 (ddd, J=16.7, 13.6, 3.8 Hz, 2H). LCMS Method C: rt 4.44 min; m/z 471.1 [M+1]+, 469.1 [M−1]−.

Aufarbeitung

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue purified by chromatography (SiO2, 0-50% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-22be701362044c13ba7d8e9f1dfeea16
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012461B2

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