Sodium Methoxide → [2-(2,6-Dichloro-benzyl)-5-methoxy-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 474314

Reaktionsgleichung

Reaktionsgleichung von HRID 474314
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:6]=1[CH2:7][C:8]1[S:9][C:10]2[N:11]=[C:12](S(C)(=O)=O)[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:15]=2[N:16]=1>C(O)(=O)C.CO>[Cl:4][C:5]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:6]=1[CH2:7][C:8]1[S:9][C:10]2[N:11]=[C:12]([O:2][CH3:1])[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:15]=2[N:16]=1

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 42641464[2-(2,6-Dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

Produkt 1

HCID 42641923[2-(2,6-Dichloro-benzyl)-5-methoxy-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To solution of NaOMe (15 mg, 0.3 mmol) and MeOH (1.5 mL) was added [2-(2,6-dichloro-benzyl)-5-methanesulfonyl-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (25 mg, 0.05 mmol) and the resulting mixture was heated to 60° C. After 4 h, the resulting solution was acidified with 1 drop of acetic acid and purified directly by reverse phase HPLC to afford a colorless solid (10.3 mg, 45%). MS (ESI): mass calcd. for C20H13Cl2F3N4OS, 484.0; m/z found, 485.0 [M+H]+. 1H NMR (CDCl3): 8.01 (s, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 7.30-7.25 (m, 1H), 4.74 (s, 2H), 4.05 (s, 3H).

Aufarbeitung

  1. custompurified directly by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-92dd154162974fa6a16d3ec6be559554
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637527B2

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