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Trifluoroacetic acid → HCID 58529273, Verbindung

HRID 1972973
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1972973
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:22]3[C:17]([C:18]([NH2:23])=[N:19][CH:20]=[N:21]3)=[C:16]([C:24]3[C:25]([F:40])=[CH:26][C:27]4[C:31]([CH:32]=3)=[N:30][N:29]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:28]=4)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O>C(Cl)Cl>[CH2:33]([N:29]1[CH:28]=[C:27]2[C:31]([CH:32]=[C:24]([C:16]3[CH:15]=[C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[N:22]4[C:17]=3[C:18]([NH2:23])=[N:19][CH:20]=[N:21]4)[C:25]([F:40])=[CH:26]2)=[N:30]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 58529448HCID 58529448, Verbindung

Produkt 1

HCID 58529273HCID 58529273, VerbindungAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[4-amino-5-(2-benzyl-5-fluoro-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester (370 mg, 0.68 mmol) in DCM (12 mL) was added trifluoroacetic acid (3 mL). The reaction was stirred at rt under N2 for 18 h and poured into EtOAc. The organic phase was washed with saturated, aqueous NaHCO3 solution, water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified via preparative HPLC. The product containing fractions were collected, and the TFA from the eluent was removed via filtration through an acidic resin followed by washing with acetonitrile. The product was then eluted with 2M NH3 in MeOH. The filtrate was concentrated and the residue was crystallized from DCM-ether-hexane to provide the title compound (166.4 mg, 55.1%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.36 (s, 1H), 7.85 (s, 1H), 7.63 (d, 1H), 7.52 (d, 1H), 7.37 to 7.54 (m, 5H), 6.63 (s, 1H), 5.66 (s, 2H), 3.52 to 3.46 (m, 1H), 3.36 to 3.30 (m, 2H), 3.28 to 3.25 (m, 1H), 3.00 (dt, 2H), 2.25 (d, 2H), 1.92 to 1.80 (m, 2H); ES-MS m/z 442.2 [M+H]+, RT (min) 2.08.

Aufarbeitung

  1. washThe organic phase was washed with saturated, aqueous NaHCO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified via preparative HPLC
  6. additionThe product containing fractions
  7. customwere collected
  8. customthe TFA from the eluent was removed via filtration through an acidic resin
  9. washby washing with acetonitrile
  10. washThe product was then eluted with 2M NH3 in MeOH
  11. concentrationThe filtrate was concentrated
  12. customthe residue was crystallized from DCM-ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fc91d1436fde4f8f951520d04f24aefb
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431695B2

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