Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178494299, compound

HRID 510438Notes

Reaction equation

HRID 510438 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]([NH2:12])=[N:7][NH:8][C:9]=1[O:10][CH3:11].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:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1[C:9]([O:10][CH3:11])=[N:8][N:7]2[C:21]([OH:22])=[CH:20][C:19]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[N:12][C:6]=12

Participants

4

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178494298HCID 178494298, compound

Product 1

HCID 178494299HCID 178494299, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(2,3-dichlorobenzyl)-5-methoxy-1H-pyrazol-3-amine (301 mg, 1.1 mmol) and ethyl 3-oxo-3-(pyridin-4-yl)propanoate (223 mg, 1.15 mmol) in acetic acid (15 mL) was stirred at 100° C. for 4 h. Then the reaction mixture was concentrated under vacuo and the residue was purified by silica gel chromatography eluted with EA to EA/MeOH=4/1, and further recrystallized with DMSO/H2O to give the titled compound (57 mg, 13%) as a yellowish solid. LC/MS: MS (ES+) m/e 402 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.89 (s, 3H), 4.00 (s, 2H), 6.07 (s, 1H), 7.03 (d, J=8.4 Hz, 1H), 7.25 (t, J=8.4 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.79 (d, J=5.1 Hz, 2H), 8.71 (d, J=5.1 Hz, 2H), 12.15 (s, 1H).

Workup

  1. concentrationThen the reaction mixture was concentrated under vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluted with EA to EA/MeOH=4/1
  4. customfurther recrystallized with DMSO/H2O

Sources & evidence

ORD record
ord-5b2404b7f1934abdb07a23c20bee53a6
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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