Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178515683, compound

HRID 510396Notes

Reaction equation

HRID 510396 reaction equation
[NH2:1][C:2]1[CH:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:4](=[O:7])[NH:5][N:6]=1.O=[C:17]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[CH2:18][C:19](OCC)=[O:20]>C(O)(=O)C>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][C:3]1[C:4]([OH:7])=[N:5][N:6]2[C:19](=[O:20])[CH:18]=[C:17]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[NH:1][C:2]=12

Participants

4

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 71270870HCID 71270870, compound

Product 1

HCID 178515683HCID 178515683, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
140 °C

Procedure

To a suspension of 5-amino-4-[(2-chlorophenyl)methyl]-2,4-dihydro-3H-pyrazol-3-one (500 mg, 2.23 mmol) in acetic acid (2 mL) was added ethyl 3-oxo-3-(4-pyridinyl)propanoate (432 mg, 2.23 mmol). The reaction mixture was irradiated (microwave) and stirred at 140° C. for 60 minutes. Reaction mixture was cooled down, diluted with acetic acid (2 mL) and stood still for 2 hours. Precipitate was collected by filtration. The solid was washed with acetic acid (1 mL), ethanol (1 mL×2) and dried. The titled product was obtained. (177 mg, 22%); LC/MS: MS (ES+) m/e 353 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 2H) 6.06 (d, J=1.52 Hz, 1H) 7.02 (s, 1H) 7.23 (dd, J=5.94, 3.41 Hz, 2H) 7.45 (dd, J=5.68, 3.66 Hz, 1H) 7.75 (d, J=6.06 Hz, 2H) 8.76 (d, J=6.06 Hz, 2H) 12.05 (s, 1H).

Workup

  1. customThe reaction mixture was irradiated (microwave)
  2. customReaction mixture
  3. temperaturewas cooled down
  4. waitstood still for 2 hours
  5. filtrationPrecipitate was collected by filtration
  6. washThe solid was washed with acetic acid (1 mL), ethanol (1 mL×2)
  7. customdried

Sources & evidence

ORD record
ord-5f0d7715b1294e50a66f2058748fc846
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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