2-(Ethoxymethylene)propanedinitrile → HCID 67024193, compound

HRID 1959527Notes

Reaction equation

CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[CH:17]1([NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([NH:29][NH2:30])[CH:23]=2)[CH2:19][CH2:18]1.C(O[CH:35]=[C:36]([C:39]#[N:40])[C:37]#[N:38])C>CCO>[NH2:40][C:39]1[N:29]([C:24]2[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=2[CH3:28])[C:21]([NH:20][CH:17]2[CH2:19][CH2:18]2)=[O:31])[N:30]=[CH:35][C:36]=1[C:37]#[N:38]

Participants

Conditions

Temperature: 65 °C

Procedure

DIPEA (3.4 g, 26.5 mmol) was added to the solution of N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetate (8.45 g, 26.5 mmol) and 2-ethoxymethylene malononitrile (3.2 g, 26.5 mmol) in EtOH (100 mL) and stirred at 65° C. for 3 h. The solvent was removed the residue was suspended in EtOAc (˜100 mL), and water was added to this suspension. The solid product was filtered. The filtrate was washed by water, brine, dried over Na2SO4, concentrated, and purified by column chromatography on silica gel eluted with EtOAc. The product, combined from filtration and chromatography, was obtained as a beige solid (7.1 g, 96%).

Workup

customThe solvent was removed the residue
additionwater was added to this suspension
filtrationThe solid product was filtered
washThe filtrate was washed by water, brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified by column chromatography on silica gel
washeluted with EtOAc
filtrationThe product, combined from filtration and chromatography

Sources & evidence

ORD record: ord-4256c0e7628f41569a5e159f692b70f9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410160B2

Reaction notes

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