Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178481487, compound

HRID 510454Notes

Reaction equation

HRID 510454 reaction equation
[NH2:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[C:5]([OH:16])[N:4]([CH3:17])[N:3]=1.O=[C:19]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[CH2:20][C:21](OCC)=[O:22]>C(O)(=O)C>[Cl:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:6]1[C:5](=[O:16])[N:4]([CH3:17])[N:3]2[C:21]([OH:22])=[CH:20][C:19]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:1][C:2]=12

Participants

4

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178481935HCID 178481935, compound

Product 1

HCID 178481487HCID 178481487, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-4-(2,3-dichlorobenzyl)-1-methyl-1H-pyrazol-5-ol (150 mg, 0.551 mmol) and ethyl 3-oxo-3-(pyridin-4-yl)propanoate (128 mg, 0.662 mmol) in acetic acid (10 mL), was stirred under reflux for 6 h. The reaction mixture was cooled, concentrated. The resulting residue was purified by silica gel chromatography eluted with DCM:MeOH=10:1 to provide the titled compound (90 mg, 41%), as a white solid; LC/MS: MS (ES+) m/e 401 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.55 (s, 3H), 3.82 (s, 2H), 6.07 (s, 1H), 7.12 (dd, J=1.2, 7.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.50 (dd, J=1.2, 7.8 Hz, 1H), 7.71 (dd, J=1.8, 4.8 Hz, 2H), 7.76 (dd, J=1.8, 4.8 Hz, 1H), 11.94 (s, 1H).

Workup

  1. temperatureunder reflux for 6 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography
  5. washeluted with DCM

Sources & evidence

ORD record
ord-4d107a9a216c4b0da9e8619ab6a3d7ad
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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