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Diisopropylethylamine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[(R)-1-(3-methyl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-3-yl]-amine

HRID 451424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 451424
Cl.Cl.[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11]C2)[S:6][N:5]=1.[CH2:16]([C:23]1[CH:28]=[C:27]([CH3:29])[N:26]=[C:25](Cl)[N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[CH2:16]([C:23]1[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH:15][C@@H:12]2[CH2:13][CH2:14][N:9]([C:7]3[S:6][N:5]=[C:4]([CH3:3])[N:8]=3)[CH2:11]2)[N:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
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Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 673442811-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine dihydrochlorideHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Produkt 1

HCID 67344305(4-Benzyl-6-methyl-pyrimidin-2-yl)-[(R)-1-(3-methyl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-3-yl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamine dihydrochloride (54.2 mg, 0.2 mmol), 4-benzyl-2-chloro-6-methyl-pyrimidine (48.1 mg, 0.22 mmol)) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in dioxane (0.6 mL) was heated at 200° C. in a microwave oven for 1 hour. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc as eluent. The title compound was obtained as a yellow viscous oil (22 mg, 29%).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous NaCl solution
  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 with EtOAc as eluent

Quellen und Nachweise

ORD-Eintrag
ord-03bba97873c043a796770718b50c609a
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486967B2

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