Hydrochloric Acid → HCID 58456275, Verbindung

HRID 410710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410710
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]2[CH:20]=[C:21]([C:26]3[S:30][C:29]([C:31]4([OH:39])[CH2:36][O:35]C(C)(C)[O:33][CH2:32]4)=[N:28][CH:27]=3)[CH:22]=[C:23]([CH3:25])[CH:24]=2)[N:13]=1)(C(C)(C)C)(C)C.Cl>O1CCCC1.CO>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]2[CH:20]=[C:21]([C:26]3[S:30][C:29]([C:31]([OH:39])([CH2:36][OH:35])[CH2:32][OH:33])=[N:28][CH:27]=3)[CH:22]=[C:23]([CH3:25])[CH:24]=2)[N:13]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 674315445-[5-(3-{[4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]-2,2-dimethyl-1,3-dioxan-5-ol

Produkt 1

HCID 58456275HCID 58456275, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-[5-(3-{[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]-2,2-dimethyl-1,3-dioxan-5-ol (185 mg, 0.32 mmol) in tetrahydrofuran (1.6 mL) was added hydrochloric acid (1.0 N, 970 μL, 0.97 mmol) at room temperature. The mixture was stirred at room temperature for 2.5 h, then diluted with methanol, filtered, and purified by reverse phase HPLC (10:90 to 90:10 acetonitrile:water with a 0.1% trifluoroacetic acid modifier). The combined fractions were dried on a lyophilizer, dissolved in methanol, and the TFA salt converted to the free base using StratoSpheres SPE PL-HCO3 MP-Resin (0.9 mmol) cartridges to give 2-[5-(3-{[4-(2-hydroxyethoxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]propane-1,2,3-triol (75 mg, 0.18 mmol, 56% yield) as a white foam. MS ESI: [M+H]+ m/z 419.1. 1H NMR (500 MHz, DMSO-d6) δ 9.65 (dd, J=4.3, 15.1, 1H), 8.21 (d, J=5.7, 1H), 7.96 (s, 1H), 7.90 (s, 1H), 7.47 (s, 1H), 7.09 (s, 1H), 6.31 (s, 1H), 4.39 (s, 2H), 3.79-3.72 (m, 2H), 3.72-3.63 (m, 4H), 2.30 (s, 3H). rhSYK activity=+++

Aufarbeitung

  1. filtrationfiltered
  2. custompurified by reverse phase HPLC (10:90 to 90:10 acetonitrile
  3. customThe combined fractions were dried on a lyophilizer
  4. dissolutiondissolved in methanol

Quellen und Nachweise

ORD-Eintrag
ord-4bd1ed48f8dd482eb7e67c8760e4e614
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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