Water → [1-(2-Methyl-pyrimidin-4-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 451402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451402
Cl.Cl.[C:3]1([CH:9]2[C:14]3[N:15]=[C:16]([NH:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:35]1[CH:40]=[CH:39][N:38]=[C:37]([CH3:41])[N:36]=1.O>CN1CCCC1=O>[CH3:41][C:37]1[N:38]=[C:39]([N:22]2[CH2:21][CH2:20][CH:19]([NH:18][C:16]3[S:17][C:13]4[CH2:12][CH2:11][CH2:10][CH:9]([C:3]5[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=5)[C:14]=4[N:15]=3)[CH2:24][CH2:23]2)[CH:40]=[CH:35][N:36]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 86656698(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride

Produkt 1

HCID 53353241[1-(2-Methyl-pyrimidin-4-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride (115.9 mg, 0.3 mmol) was dissolved in N-methylpyrrolidone (3 mL). N,N-diisopropylethylamine (165 1, 0.96 mmol) and 4-chloro-2-methylpyrimidine (44.7 mg, 0.33 mmol) were added at room temperature under nitrogen and stirring. The reaction was heated in a microwave oven to 200° C. for 30 minutes. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient from EtOAc to EtOAc/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a light yellow viscous oil (34 mg, 28%).

Aufarbeitung

  1. extractionthe reaction was extracted twice with diethyl ether
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using a gradient from EtOAc to EtOAc/EtOH 9:1 (v/v) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-740feb79d58b4f46902d8ba06146f01b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

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