Water → 1-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone

HRID 2067133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067133
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1.[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][N:33]([C:2]3[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][C:12]4[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=4)[N:5]=[CH:4][N:3]=3)[CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 242088454-(3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl)piperidineHCID 859844451-[4-Chloro-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone

Produkt 1

HCID 582164601-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanoneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-[4-chloro-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone (0.21 mmol, 70 mg) and 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine (0.21 mmol, 49 mg) in N,N-dimethyl formamide (500 uL) was added potassium carbonate (0.21 mmol, 29 mg). The mixture was microwaved at 100° C. for 150 seconds. Its progress was monitored by thin layer chromatography and LCMS. The reaction was treated with water and the desired compound was extracted in ethyl acetate. Organic layer was evaporated in vacuo. Purification by HPLC provided Compound A165 as a white solid (20 mg, 20%). 1H-NMR (400 MHz, CDCl3) δ(ppm): 8.24 (s, 1H); 8.01 (d, 2H); 7.32 (d, 2H); 4.02 (m, 2H); 3.22 (m, 3H); 3.10 (m, 1H); 3.08 (s, 3H); 2.69 (s, 3H), 2.18 (m, 2H), 2.02 (m, 2H); 1.35 (d, 6H). LCMS (ESI), m/z 486.3 (M+H+, 100%).

Aufarbeitung

  1. customThe mixture was microwaved at 100° C. for 150 seconds
  2. extractionthe desired compound was extracted in ethyl acetate
  3. customOrganic layer was evaporated in vacuo
  4. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-422d6efb945e4a898727c0ca7c6479c1
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293751B2

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