HCID 69039450, compound → HCID 69042265, compound

HRID 397869Notes

Reaction equation

HRID 397869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][C:21](=O)[CH3:22])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH2:21][CH3:22])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 69039450HCID 69039450, compound

Product 1

HCID 69042265HCID 69042265, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

N-{1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-ylmethyl]-1H-imidazol-2-yl}-acetamide (0.30 g, 0.86 mmol) was treated with 1M BH3 THF complex (1.6 ml) and refluxed for 2 h. The mixture was cooled to 5° C. and MeOH (5 ml) was added slowly. After evaporation of all volatiles the residue was taken up in 2N HCl solution (3 ml) and refluxed for 20 min. The mixture was cooled and 2N NaOH solution (3 ml) was added. After extraction with AcOEt (50 ml), the organic phase was dried (Na2SO4) and evaporated to dryness. Purification by chromatography [silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] gave the free base of the title compound. After treatment with a solution of HCl in MeOH followed by addition of Et2O the title compound was isolated as an off-white crystalline material (0.062 g, 22%). Mp.>250° C. (MeOH/Et2O), MS: m/e=336 (M+H′).

Workup

  1. temperaturerefluxed for 2 h
  2. customAfter evaporation of all volatiles the residue
  3. temperaturerefluxed for 20 min
  4. temperatureThe mixture was cooled
  5. addition2N NaOH solution (3 ml) was added
  6. extractionAfter extraction with AcOEt (50 ml)
  7. dry with materialthe organic phase was dried (Na2SO4)
  8. customevaporated to dryness
  9. customPurification
  10. washby chromatography [silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)]

Sources & evidence

ORD record
ord-017476454679421eb030e0d82127c46f
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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