Triethylamine → HCID 24853217, compound

HRID 599655Notes

Reaction equation

HRID 599655 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6](/[CH:16]=[CH:17]/[C:18](=[NH:22])OCC)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1.C(N(CC)CC)C.Cl.Cl[CH2:32][CH2:33][CH2:34][CH:35]([C:40]1[CH:45]=[CH:44][C:43]([N:46]([CH3:48])[CH3:47])=[CH:42][CH:41]=1)[C:36]([NH:38][NH2:39])=O>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6](/[CH:16]=[CH:17]/[C:18]2[N:22]=[C:36]3[CH:35]([C:40]4[CH:45]=[CH:44][C:43]([N:46]([CH3:48])[CH3:47])=[CH:42][CH:41]=4)[CH2:34][CH2:33][CH2:32][N:38]3[N:39]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 67067302HCID 67067302, compoundHCID 67067458HCID 67067458, compound

Product 1

HCID 24853217HCID 24853217, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 4 N hydrochloric acid in ethyl acetate (2.64 mL) was added to tert-butyl N′-[5-chloro-2-(4-dimethylaminophenyl)pentanoyl]hydrazinecarboxylate (106.9 mg), and the reaction solution was stirred at room temperature for four hours. The reaction solution was concentrated under reduced pressure to obtain 5-chloro-2-(4-dimethylaminophenyl)pentanoic acid hydrazide hydrochloride. A solution of ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate hydrochloride (77.6 mg) and triethylamine (0.16 mL) in ethanol (1.25 mL) was added to a solution of the resulting 5-chloro-2-(4-dimethylaminophenyl)pentanoic acid hydrazide hydrochloride and triethylamine (0.291 mL) in ethanol (1.25 mL), and the reaction solution was stirred at 80° C. in a nitrogen atmosphere for 22 hours. The reaction solution was cooled to room temperature, and then the solvent was evaporated from the reaction solution under reduced pressure. Ethyl acetate and saturated sodium bicarbonate water were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1) and further purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=9:1) to obtain 26.6 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was evaporated from the reaction solution under reduced pressure
  3. additionEthyl acetate and saturated sodium bicarbonate water were added to the resulting residue
  4. customthe organic layer was separated
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1)
  9. customfurther purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-3750e6219acf4514ba089e87cd93d3f8
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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