Triethylamine → HCID 178433996, compound

HRID 1040455Notes

Reaction equation

HRID 1040455 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:19])[NH:11][C:12]1([C:15]([NH:17][NH2:18])=O)[CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C(O[C:24](=[NH:26])[CH3:25])C.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:2]([O:9][C:10](=[O:19])[NH:11][C:12]1([C:15]2[NH:26][C:24]([CH3:25])=[N:18][N:17]=2)[CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 67390878HCID 67390878, compound

Product 1

HCID 178433996HCID 178433996, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a vial was added (1-hydrazinocarbonyl-cyclopropyl)-carbamic acid benzyl ester HCl salt (300 mg, 1.05 mmol), acetimidic acid ethyl ester HCl salt (195 mg, 1.58 mmol) and triethylamine (320 mg, 3.16 mmol) in toluene (8 ml). The reaction mixture was stirred at 120° C. for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc/sat. NaHCO3. The organic phase was separated, washed with brine, dried under anhy. Na2SO4, filtered and concentrated. The residue was purified by prepHPLC to afford 57 mg of [1-(5-methyl-4H-[1,2,4]triazol-3-yl)-cyclopropyl]-carbamic acid benzyl ester, m/z 273.6 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc/
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried under anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated
  8. customThe residue was purified by prepHPLC

Sources & evidence

ORD record
ord-06aef9de875547e8a10e5b1927c9da2a
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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