Diisopropylethylamine → [1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 451403

Reaktionsgleichung

Reaktionsgleichung von HRID 451403
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.Cl.Cl.[C:28]1([CH:34]2[C:39]3[N:40]=[C:41]([NH:43][CH:44]4[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]4)[S:42][C:38]=3[CH2:37][CH2:36][CH2:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)C(C)C)(C)C.Cl[C:60]1[S:64][N:63]=[C:62]([CH3:65])[N:61]=1>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:65][C:62]1[N:61]=[C:60]([N:47]2[CH2:46][CH2:45][CH:44]([NH:43][C:41]3[S:42][C:38]4[CH2:37][CH2:36][CH2:35][CH:34]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:39]=4[N:40]=3)[CH2:49][CH2:48]2)[S:64][N:63]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazoleHCID 86656698(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride

Produkt 1

HCID 53354635[1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Palladium (II) acetate (3.6 mg, 0.016 mmol) and 2-(dicyclohexylphosphino)biphenyl (11.6 mg, 0.032 mmol) were stirred under nitrogen at room temperature in dioxane (1.8 mL) for 10 minutes. Sodium tert.-butylat (29 mg, 0.3 mmol), (4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-piperidin-4-yl-amine dihydrochloride (77.3 mg, 0.2 mmol), N,N-diisopropylethylamine (69 L, 0.4 mmol) and 5-chloro-3-methyl-[1,2,4]thiadiazole (29.6 mg; 0.22 mmol) were added and the reaction was heated to 200° C. for 30 minutes in a microwave oven. The reaction was diluted with water and extracted twice with ethyl acetate. 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 heptane/EtOAc 4:1 to 1:4 (v/v) as eluent. The title compound was obtained as a white solid (55 mg, 67%).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  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

Quellen und Nachweise

ORD-Eintrag
ord-128b987ab884452eb996b211b380ab22
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

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