3-Amino-2-butenenitrile → Cyclobutylmethyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 557434

Reaction equation

HRID 557434 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:23](=O)[CH3:24])[C:15]([O:17][CH2:18][CH:19]1[CH2:22][CH2:21][CH2:20]1)=[O:16].[NH2:26][C:27]([CH3:31])=[CH:28][C:29]#[N:30]>C(O)C>[C:29]([C:28]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:14]([C:15]([O:17][CH2:18][CH:19]2[CH2:22][CH2:21][CH2:20]2)=[O:16])=[C:23]([CH3:24])[NH:26][C:27]=1[CH3:31])#[N:30]

Participants

4

Reactant 2

HCID 706993-Amino-2-butenenitrileHCID 66991437Cyclobutylmethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Product 1

HCID 66991699Cyclobutylmethyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

66 mg (0.19 mmol) of cyclobutylmethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate are dissolved with 16 mg (0.19 mmol) of 3-aminobut-2-enenitrile in 3 ml of ethanol and heated under reflux under argon for 24 h. The suspension is allowed to cool and filtered with suction, and the remaining solid is washed with methanol. 45 mg (57% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 24 h
  3. temperatureto cool
  4. filtrationfiltered with suction
  5. washthe remaining solid is washed with methanol

Sources & evidence

ORD record
ord-edeaa721f70e43b99b5e054abe3f32d3
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Linked notes

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