Lithium Carbonate → HCID 59153175, compound

HRID 2355302Notes

Reaction equation

HRID 2355302 reaction equation
C(=O)([O-])[O-].[Li+].[Li+].[Br:7][C:8]1[C:9]([OH:20])=[C:10]([C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:12][C:13]=1[OH:14].I[CH2:22][C:23]1[CH:38]=[CH:37][C:26]([CH2:27][NH:28][C:29]([C:31]2[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=2)=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[Br:7][C:8]1[C:9]([OH:20])=[C:10]([C:15](=[O:19])[CH:16]([CH3:17])[CH3:18])[CH:11]=[CH:12][C:13]=1[O:14][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:28][C:29]([C:31]2[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=2)=[O:30])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 11125Lithium Carbonate2×HCID 67176206HCID 67176206, compoundHCID 68451982HCID 68451982, compound3×

Product 1

HCID 59153175HCID 59153175, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Add lithium carbonate (24 mg, 324 μmol) to 1-(3-bromo-2,4-dihydroxy-phenyl)-2-methyl-propan-1-one (70 mg, 270 μmol) and N-(4-(iodomethyl)benzyl)-1-methyl-1H-imidazole-4-carboxamide (106 mg, 297 μmol) in anhydrous dimethylformamide (4 mL). Warm the reaction mixture to 50° C. and stir for 1.5 hrs. Add additional N-(4-(iodomethyl)benzyl)-1-methyl-1H-imidazole-4-carboxamide (20 mg, 56 μmol) and stir for 1 hr at 50° C. Add additional lithium carbonate (24 mg, 324 μmol) and N-(4-(iodomethyl)benzyl)-1-methyl-1H-imidazole-4-carboxamide (20 mg, 56 μmol) and stir overnight at 50° C. Cool the reaction mixture to room temperature and quench with water. Extract the aqueous mixture with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate. Purify the residue by reverse phase HPLC using gradient 90/10 to 20/80 (water/0.1% trifluoroacetic acid)/acetonitrile as eluent to give the title compound (22 mg, 45 μmol). MS (m/z): 487 (M+1).

Workup

  1. stirringstir for 1 hr at 50° C
  2. stirringstir overnight at 50° C
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with water
  5. extractionExtract the aqueous mixture with ethyl acetate (3×)
  6. washCombine the organic layers, wash with brine
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate
  9. customPurify the residue by reverse phase

Sources & evidence

ORD record
ord-ae6bebdc900743a2bb33ec03a9f86007
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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