Diisopropylethylamine → ethyl (E)-3-[(E)-aminomethylideneamino]-2-cyano-3-[(4-methoxyphenyl)methylamino]prop-2-enoate

HRID 1052386Notes

Reaction equation

HRID 1052386 reaction equation
[C:1](/[C:3](=[C:9](/[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)\SC)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(N(CC)C(C)C)(C)C.Cl.[CH:32]([NH2:34])=[NH:33]>C(O)C>[NH2:34]/[CH:32]=[N:33]/[C:9](/[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[C:3](\[C:1]#[N:2])/[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 131736126(E)-Ethyl 2-cyano-3-((4-methoxybenzyl)amino)-3-(methylthio)acrylate

Product 1

HCID 140693035ethyl (E)-3-[(E)-aminomethylideneamino]-2-cyano-3-[(4-methoxyphenyl)methylamino]prop-2-enoateYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-Ethyl 2-cyano-3-((4-methoxybenzyl)amino)-3-(methylthio)acrylate was dissolved in 65 mL ethanol. N,N-Diisopropylethylamine (13 mL, 74.44 mmol) and formamidine hydrochloride (2.12 g, 26.33 mmol) were added and the reaction mixture was stirred at room temperature for 48 h. The solvent was concentrated and the residue was directly purified using SP1® Purification System (0% to 10%, dichloromethane-methanol) to give 0.96 g (25% yield) of the title compound as a yellow oil. Purity 85%.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was directly purified
  3. customSP1® Purification System (0% to 10%, dichloromethane-methanol)

Sources & evidence

ORD record
ord-481c52aaed3041dab195f422e109fc60
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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