Ethyl Acetate → HCID 69041919, compound

HRID 1841206Notes

Reaction equation

HRID 1841206 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH:15][C:16]3[NH:17][CH:18]=[CH:19][N:20]=3)[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].[CH3:23]COC(C)=O>C(OCC)(OCC)OCC.[Cl-].[Na+].O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:23]=[CH:18][N:17]=[C:16]3[NH:20][CH3:19])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86589924HCID 86589924, compound

Product 1

HCID 69041919HCID 69041919, compound

Reagents, catalysts & solvents 2

HCID 31214Ethyl orthoformateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 1-[[1-(3,4-dichloro-phenyl)-1H-imidazol-4-ylmethyl]-1H-imidazol-2-ylamine (0.7 g, 2.3 mmol) in triethyl orthoformate (10 ml) was stirred under reflux for 2 h. The reaction mixture was evaporated to dryness, dissolved in ethanol (10 ml) and cooled in an ice bath. Sodium borohydride (0.091 g, 2.4 mmol) was added and the mixture was allowed to slowly reach 20° C. After 18 h AcOEt and brine was added and the organic phase was separated, dried (Na2SO4) and concentrated. After chromatography [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] the free base of the title compound was obtained. It was crystallized as the off-white hydrochloride salt (0.25 g, 16%). Mp. >250° C. (MeOH/Et2O), MS: m/e=322 (M+H+).

Workup

  1. temperatureunder reflux for 2 h
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutiondissolved in ethanol (10 ml)
  4. temperaturecooled in an ice bath
  5. customwas allowed to slowly reach 20° C
  6. customthe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. washAfter chromatography [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] the free base of the title compound
  10. customwas obtained
  11. customIt was crystallized as the off-white hydrochloride salt (0.25 g, 16%)

Sources & evidence

ORD record
ord-7919f486830d4ddd9d18e75797ea03cc
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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