Trifluoroacetic acid → HCID 71596821, Verbindung

HRID 405069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405069
[CH3:1][N:2]([CH3:55])[CH:3]([C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1)[CH2:4][NH:5][CH2:6][C@:7]12[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:42])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:41]=[CH:40][C:32]([C:33]([O:35]C(C)(C)C)=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:55][N:2]([CH3:1])[CH:3]([C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1)[CH2:4][NH:5][CH2:6][C@:7]12[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:42])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:27])([CH3:28])[C:16]([C:29]2[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:40][CH:41]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86676408HCID 86676408, Verbindung

Produkt 1

HCID 71596821HCID 71596821, VerbindungAusbeute 13,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(dimethylamino)-2-(pyridin-3-yl)ethylamino)methyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (125 mg, 0.167 mmol) in DCM (1 ml) was added TFA (0.4 ml, 5.19 mmol). The mixture was stirred at rt for 4.5 h then was concentrated under reduced pressure. The residue was dissolved in dioxane and MeOH and was purified by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure. Impurities were still present so the residue was purified again by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to give the title compound as an off-white solid (16 mg, 13.8%). LCMS: m/e 692.5 (M+H)+, 2.30 min (method 6). 1H NMR (500 MHz, Acetic Acid) δ ppm 8.83-8.98 (m, 2H), 8.27-8.42 (m, 1H), 7.99-8.11 (m, 2H), 7.71-7.84 (m, 1H), 7.27-7.35 (m, 2H), 5.33-5.42 (m, 1H), 5.22-5.30 (m, 1H), 4.79 (d, J=14.34 Hz, 1H), 4.67 (d, J=12.82 Hz, 1H), 4.21-4.38 (m, 2H), 3.34-3.52 (m, 1H), 2.97-3.15 (m, 1H), 2.83 (br. s., 3H), 2.82 (br. s., 3H), 2.43-2.58 (m, 1H), 0.88-2.23 (m, 40H).

Aufarbeitung

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dioxane
  3. customMeOH and was purified by prep HPLC
  4. additionThe fractions containing the expected product
  5. concentrationconcentrated under reduced pressure
  6. customwas purified again by prep HPLC
  7. additionThe fractions containing the expected product
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4a603e1c11d44b759bc7721d4fddfeac
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748415B2

Notizen zur Reaktion

Wird geladen…