Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178437905, compound

HRID 510423Notes

Reaction equation

HRID 510423 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1[C:6]([CH2:11][CH3:12])=[N:7][NH:8][C:9]=1[NH2:10].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.O>[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1[C:6]([CH2:11][CH3:12])=[N:7][N:8]2[C:21]([OH:22])=[CH:20][C:19]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:10][C:9]=12

Participants

5

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178438049HCID 178438049, compound

Product 1

HCID 178437905HCID 178437905, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(2,3-dichlorobenzyl)-3-ethyl-1H-pyrazol-5-amine (250 mg, 0.93 mmol), ethyl 3-oxo-3-(pyridin-4-yl)propanoate (198 mg, 1.03 mmol) in acetic acid (10 mL) and water (0.5 mL) was stirred at 120° C. for 20 h, cooled and the pH was carefully adjusted to 8. The mixture was extracted with DCM (100 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column (PE:EA=10:1) to give the titled compound (95 mg, 26%); LC/MS: MS (ES+) m/e 399 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.12 (t, J=7.5 Hz, 3H), 2.56 (q, J=7.5 Hz, 2H), 4.07 (s, 2H), 5.97 (s, 1H), 7.16-7.21 (m, 2H), 7.42 (d, 2.1 Hz, 1H), 7.90 (dd, J=1.5, 4.5 Hz, 1H), 8.56 (dd, J=1.5, 4.5 Hz, 1H).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with DCM (100 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column (PE:EA=10:1)

Sources & evidence

ORD record
ord-2589d6a6e50248aea91371e49d6c6773
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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