Bis-(1H-imidazol-2-YL)-methanone → HCID 54684212, compound

HRID 1013011Notes

Reaction equation

HRID 1013011 reaction equation
[CH2:1]([N:8]([CH3:30])[CH2:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:18])[C:14]([OH:28])=[C:13]([OH:29])[N:12]=1)C1C=CC=CC=1.C(C1NC=CN=1)(C1NC=CN=1)=[O:32].CC(C)([O-])C.[K+]>[Pd].O1CCOCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:17]([C:15]2[N:16]=[C:11]3[CH2:10][CH2:9][N:8]([CH3:1])[C:30](=[O:32])[N:12]3[C:13](=[O:29])[C:14]=2[OH:28])=[O:18])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 23665647Potassium tert-butoxideHCID 178483320HCID 178483320, compound

Product 1

HCID 54684212HCID 54684212, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A methanolic solution of 2-{2-[benzyl(methyl)amino]ethyl}-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide prepared as described in Step 4 was stirred under H2 atmosphere in the presence of catalytic 10% Pd/C for 2 hours. The reaction mixture was filtered through celite to remove the catalyst then concentrated under reduced pressure. MS (ES) C17H17FN4O3 requires 320. Found: 321 (M+H+). The crude organic product was treated with carbonyl diimidazole (1.5 equivalents) and potassium tert-butoxide in refluxing dioxane for 1 hour. Title compound was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant). Lyophilization of appropriate fractions gave title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customto remove the catalyst
  3. concentrationthen concentrated under reduced pressure
  4. customTitle compound was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-f2a1850d2df0446ab2fb35f2c53d3cb4
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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