Diisopropylethylamine → [3-(2-Methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine

HRID 1186499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186499
Cl[C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][N:7]=1.[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH2:27])[CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:18][S:17][C:13]1[N:12]=[C:11]([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH:27][CH2:26][CH2:25][N:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)[C:3]3=[N:10][CH:9]=2)[CH:16]=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 866709158-Chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 68226490[3-(2-Methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of 8-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine (from Example 44 supra) (400 mg, 1.44 mmol) in iPrOH (20 mL) was added 2-morpholino-ethanamine (244 mg, 1.88 mmol) followed by diisopropylethylamine (242 mg, 1.88 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was removed under reduced pressure. The residue was extracted with dichloromethane (150 mL) and washed with water (3×25 mL), dried over anhydrous sodium sulfate and concentrated to afford [3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine. (Yield 410 g, 76.8%). LC-MS: [M+H]+ 372.

Aufarbeitung

  1. temperatureat reflux for 15 hours
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (150 mL)
  4. washwashed with water (3×25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc2b2356925b4da38eb881b7aa45088b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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