Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178422942, compound

HRID 510382Notes

Reaction equation

HRID 510382 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]1[C:14]([NH2:18])=[N:15][NH:16][CH:17]=1.O=[C:20]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[CH2:21][C:22](OCC)=[O:23]>C(O)(=O)C>[CH3:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]1[CH:17]=[N:16][N:15]2[C:22]([OH:23])=[CH:21][C:20]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[N:18][C:14]=12

Participants

4

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178422938HCID 178422938, compound

Product 1

HCID 178422942HCID 178422942, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (115 mg, 0.45 mmol) in acetic acid (2.0 mL) was added ethyl 3-oxo-3-(4-pyridinyl)propanoate (87 mg, 0.45 mmol) in a microwave reaction vessel. It was sealed and irradiated (microwave) at 140° C. for 60 minutes. The reaction mixture was cooled and stood for 2 hours. Precipitate was observed, filtered. Solid was washed with acetic acid (1 mL), then ethanol (1 mL×2). Solid was dried. The titled compound was obtained. (87 mg, 50%); LC/MS: MS (ES+) m/e 385 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H) 4.12 (s, 2H) 6.14 (s, 1H) 7.34 (s, 2H) 7.56 (d, J=9.09 Hz, 1H) 7.67 (s, 1H) 7.81 (br. s., 2H) 8.78 (br. s., 2H) 12.37 (br. s., 1H).

Workup

  1. customin a microwave reaction vessel
  2. customIt was sealed
  3. customirradiated (microwave) at 140° C. for 60 minutes
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. washSolid was washed with acetic acid (1 mL)
  7. customSolid was dried

Sources & evidence

ORD record
ord-0cc6bb22c3b04cbfbe42d8cfbdbd0a43
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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