Triethylamine → (3-((3-(3,6-Dihydro-2H-pyran-4-YL)pyridin-2-YL)oxy)azetidin-1-YL)(pyrimidin-4-YL)methanone

HRID 2207848

Reaktionsgleichung

Reaktionsgleichung von HRID 2207848
Cl.[NH:2]1[CH2:5][CH:4]([O:6][C:7]2[C:12]([C:13]3[CH2:14][CH2:15][O:16][CH2:17][CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:3]1.[N:19]1[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[N:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:16]1[CH2:15][CH:14]=[C:13]([C:12]2[C:7]([O:6][CH:4]3[CH2:3][N:2]([C:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][N:21]=4)=[O:26])[CH2:5]3)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 1693064-Pyrimidinecarboxylic acidHCID 674774502-(Azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-YL)pyridine hydrochloride

Produkt 1

HCID 58547745(3-((3-(3,6-Dihydro-2H-pyran-4-YL)pyridin-2-YL)oxy)azetidin-1-YL)(pyrimidin-4-YL)methanoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-yl)pyridine hydrochloride (see PREPARATION P26.1; 100 mg, 0.45 mmol), pyrimidine-4-carboxylic acid (55 mg, 0.45 mmol) and triethylamine (96.13 mg, 0.95 mmol) in CH2Cl2 (10 mL) was added 4-Dimethylaminopyridine (DMAP) (55 mg, 0.47 mmol) and propyl phosphonic anhydride (500 mg, 0.9 mmol). The reaction mixture was stirred at room temperature for overnight. Then the reaction mixture was concentrated and the crude product was purified by silica gel column chromatography to give the desired compound (48 mg, 0.16 mmol, yield 66%). [M+1]: 339. IC50 (uM): 0.99.

Aufarbeitung

  1. concentrationThen the reaction mixture was concentrated
  2. customthe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-302a20444cd74767a1c4bfcedc7c9482
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376450B2

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