Benzaldehyde → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 916651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916651
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][NH2:21])[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.BrBr.[CH3:35]CO>>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:35][N:20]4[N:21]=[C:18]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[N:17]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 240BenzaldehydeHCID 702EthanolHCID 24408BromineHCID 57503304{6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine

Produkt 1

HCID 113045167-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Versuchsvorschrift

A mixture of {6-[2-(3,-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine (131) (60 mg, 0.18 mmol), benzaldehyde (21 mg, 0.2 mmol) in EtOH is refluxed for 4 hours. Solvent is removed in vacuo. HOAc (2 mL) is added to the residue, and then bromine (0.3 mmol) is slowly added. The mixture is stirred at room temperature overnight. Solvent is removed in vacuo and the residue is treated with NaHCO3 (aq) and DCM. The organic layer is separated and the aqueous layer is extracted with DCM (2×0 mL). The combined organic layers are dried (MgSO4), the solvent is removed, and the crude purified by PTLC (10% MeOH in DCM) to give a white solid; 1H-NMR (CDCl3) δ: 8.93 (s, 1H), 8.44 (dd, 1H), 7.78–7.88 (m, 2H), 7.51–7.63 (m, 4H), 7.22–7.36 (m, 3H), 5.82 (s, 2H), 3.05 (q, 2H), 1.70–1.80 (m, 2H), 1.02 (t, 3H).

Aufarbeitung

  1. temperatureis refluxed for 4 hours
  2. customSolvent is removed in vacuo
  3. additionHOAc (2 mL) is added to the residue
  4. customSolvent is removed in vacuo
  5. additionthe residue is treated with NaHCO3 (aq) and DCM
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted with DCM (2×0 mL)
  8. dry with materialThe combined organic layers are dried (MgSO4)
  9. customthe solvent is removed
  10. customthe crude purified by PTLC (10% MeOH in DCM)
  11. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-ce530d4ec1374af4987022e6a833c09d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271170B2

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