2-Bromopyrimidine → 2-[3-(1-Pyrimidin-2-ylpiperidin-4-ylmethyl)-[1,2,4]oxadiazol-5-yl]furo[3,2-c]pyridine

HRID 217196

Reaktionsgleichung

Reaktionsgleichung von HRID 217196
C1CC[N:9]2[C:4](=[N:5][CH2:6][CH2:7][CH2:8]2)CC1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]2[N:23]=[C:22]([C:24]3[O:32][C:31]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4[CH:25]=3)[O:21][N:20]=2)[CH2:14][CH2:13]1.BrC1N=CC=CN=1>O1CCOCC1>[N:9]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]2[N:23]=[C:22]([C:24]3[O:32][C:31]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4[CH:25]=3)[O:21][N:20]=2)[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 783452-BromopyrimidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 116305842-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine

Produkt 1

HCID 576594452-[3-(1-Pyrimidin-2-ylpiperidin-4-ylmethyl)-[1,2,4]oxadiazol-5-yl]furo[3,2-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

DBU (53 ΔL, 352 Amos) was added to a stirred solution of 2-(3-piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine (Preparation 12, 50 mg, 176 μmol) and 2-bromopyrimidine (31 mg, 193 μmol) in dioxane (1 mL) at 20° C. After 2 d, the solvent was removed in vacuo, then the residue was purified by chromatography (MeOH—CH2Cl2, 1:19) to yield the title compound: RT=2.64 min; m/z (ES+)=363.1 [M+H]+.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (MeOH—CH2Cl2, 1:19)

Quellen und Nachweise

ORD-Eintrag
ord-5dc9b5405800447db90dd76ea6f92d39
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193359B2

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