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Trifluoroacetic acid → 7-(2-(2-((4-(Piperazin-1-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)isoindolin-1-one

HRID 1473080
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473080
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[N:14]=2)[CH2:4][NH:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:30]1([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:15]3[N:14]=[C:13]([CH2:12][CH2:11][C:9]4[CH:8]=[CH:7][CH:6]=[C:5]5[C:10]=4[C:2](=[O:1])[NH:3][CH2:4]5)[C:18]([C:19]([F:20])([F:21])[F:22])=[CH:17][N:16]=3)=[CH:29][CH:28]=2)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 86675720tert-Butyl 4-(4-((4-(2-(3-oxoisoindolin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate

Produkt 1

HCID 712089477-(2-(2-((4-(Piperazin-1-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)isoindolin-1-oneAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

tert-Butyl 4-(4-((4-(2-(3-oxoisoindolin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (I63) (0.080 g, 0.137 mmol) was dissolved in DCM (5 mL) under an atmosphere of nitrogen. Trifluoroacetic acid (0.210 mL, 2.75 mmol) was added to the solution and the reaction was stirred at room temperature for 1 hour and then at 35° C. for another 30 minutes. More trifluoroacetic acid (0.100 mL) was added and the reaction was further stirred at 35° C. for another 30 minutes. Volatiles were removed in vacuo then EtOAc (70 mL) and 2 M aq. NaOH (70 mL) were added to the residue and the layers were separated. The aqueous layer was extracted with EtOAc (2×70 mL), the combined organics were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo to give an oily solid which was taken up in DCM (˜10 mL) and concentrated in vacuo. The process was repeated twice after which the sample was further dried on high-vacuum to give the title compound (15) (0.050 g, 75% yield) as an off-white solid; 1H NMR (400 MHz, d6-DMSO) δ 9.94 (s, 1H), 8.56 (s, 1H), 8.48 (s, 1H), 7.59-7.52 (m, 2H), 7.47-7.36 (m, 2H), 7.23-7.11 (m, 1H), 6.87 (d, J=9.0 Hz, 2H), 4.31 (s, 2H), 3.56 (t, J=7.6 Hz, 2H), 3.11 (t, J=7.4 Hz, 2H), 3.01-2.95 (m, 4H), 2.86-2.79 (m, 4H). LCMS Method A: rt 4.40 min; m/z 483.8 [M+H]+.

Aufarbeitung

  1. waitat 35° C. for another 30 minutes
  2. stirringthe reaction was further stirred at 35° C. for another 30 minutes
  3. customVolatiles were removed in vacuo
  4. additionEtOAc (70 mL) and 2 M aq. NaOH (70 mL) were added to the residue
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc (2×70 mL)
  7. washthe combined organics were washed with water (50 mL), brine (50 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give an oily solid which
  12. concentrationconcentrated in vacuo
  13. customwas further dried on high-vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2cd0f1462d6d45e88adb11ac588ce3ef
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012461B2

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