Acetic Acid → Cyclobutyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 557393Notes

Reaction equation

HRID 557393 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]=O.O=[C:16]([CH3:25])[CH2:17][C:18]([O:20][CH:21]1[CH2:24][CH2:23][CH2:22]1)=[O:19].[NH2:26]/[C:27](/[CH3:31])=[CH:28]\[C:29]#[N:30].C(O)(=O)C>CC(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:17]([C:18]([O:20][CH:21]2[CH2:24][CH2:23][CH2:22]2)=[O:19])=[C:16]([CH3:25])[NH:26][C:27]=1[CH3:31])#[N:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 20189390Cyclobutyl 3-oxobutanoate

Product 1

HCID 15978969Cyclobutyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

60 mg (0.32 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 49.7 mg (0.32 mmol) of cyclobutyl 3-oxobutanoate, 26.2 mg (0.32 mmol) of 3-aminocrotononitrile and 19.1 mg (0.32 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 4 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 64 mg (51% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-07d8137e2e3847a9889d5951a7d651e1
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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