4-Amino-3-penten-2-one → HCID 57503351, compound

HRID 1669792Notes

Reaction equation

HRID 1669792 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:22](=O)[CH3:23])[C:15]([O:17][CH2:18][CH:19]1[CH2:21][CH2:20]1)=[O:16].[NH2:25][C:26]([CH3:31])=[CH:27][C:28](=[O:30])[CH3:29]>C(O)C>[C:28]([C:27]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[CH2:21][CH2:20]2)=[O:16])=[C:22]([CH3:23])[NH:25][C:26]=1[CH3:31])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 1368734-Amino-3-penten-2-oneHCID 67342865HCID 67342865, compound

Product 1

HCID 57503351HCID 57503351, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

648 mg (1.98 mmol) of cyclopropylmethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate are dissolved with 196 mg (1.98 mmol) of 4-aminopent-3-en-2-one in 10 ml of ethanol and heated under reflux under argon for 24 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. Concentration of the product fractions and crystallization from ethyl acetate result in 327 mg (41% of theory) of the title compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 24 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC
  5. customConcentration of the product fractions and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-843be9352e124a94840983ca4afbdc99
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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