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

HRID 474307

Reaktionsgleichung

Reaktionsgleichung von HRID 474307
Cl[C:2]1[C:3]2[N:10]=[C:9]([CH2:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1.Cl>C(O)(C)C>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[CH2:11][C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([C:21]([F:20])([F:29])[F:30])=[CH:23][CH:24]=3)[C:3]=2[N:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 577424637-Chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine

Produkt 1

HCID 42642137[2-(2,6-Dichloro-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 7-chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine (45.0 mg, 0.15 mmol) and 4-trifluoromethyl-phenylamine (23 mg, 0.15 mmol) in isopropanol (IPA) (2 mL) was added 1.25 M HCl in IPA (0.26 mL, 0.32 mmol). The resulting solution was heated in a sealed tube to 90° C. After 12 h, the solution was cooled and purified by preparative reverse-phase HPLC to afford the title compound as a colorless solid (50 mg, 74%). MS (ESI): mass calcd. for C19H11Cl2F3N4S, 454.0; m/z found, 455.0 [M+H]+. 1H NMR ((CD3)2SO): 10.46 (s, 1H), 8.58 (s, 1H), 8.19 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.1 Hz, 2H), 7.47 (dd, J=8.5, 7.8 Hz, 1H), 4.82 (s, 2H).

Aufarbeitung

  1. temperaturethe solution was cooled
  2. custompurified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6c8e3ec7d8ba481bbb90572ae8312ea9
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637527B2

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