1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamine → HCID 178507164, compound

HRID 1040454Notes

Reaction equation

HRID 1040454 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2([NH2:15])[CH2:14][CH2:13]2)[N:9]=[CH:8]1>CCO.Cl>[NH:7]1[CH:11]=[C:10]([C:12]2([NH2:15])[CH2:14][CH2:13]2)[N:9]=[CH:8]1

Participants

4

Reactant 1

HCID 584311581-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamine

Product 1

HCID 178507164HCID 178507164, compoundYield 137.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamine (400 mg, 1.58 mmol) in EtOH (20 ml) and 3N HCl (15 ml). The reaction mixture was stirred at 90° C. for 4 h. The reaction mixture was concentrated in vacuo. The residue was purified by prepHPLC by eluting with 0.5% acetonitrile/water to afford 267 mg of 1-(1H-imidazol-4-yl)-cyclopropylamine as a formic acid salt, m/z 124 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by prepHPLC
  3. washby eluting with 0.5% acetonitrile/water

Sources & evidence

ORD record
ord-0842b7f10f9e4e58ae58606595486f37
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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