Ethyl 3-(4-pyridyl)-3-oxopropionate → HCID 178424860, compound

HRID 510385Notes

Reaction equation

HRID 510385 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[C:6]([NH2:10])=[N:7][NH:8][CH:9]=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>[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[CH:9]=[N:8][N:7]2[C:19]([OH:20])=[CH:18][C:17]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[N:10][C:6]=12

Participants

4

Reactant 2

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 178424859HCID 178424859, compound

Product 1

HCID 178424860HCID 178424860, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(2,3-dimethylbenzyl)-1H-pyrazol-3-amine (189 mg, 0.93 mmol) in acetic acid (2.0 mL) was added ethyl 3-oxo-3-(4-pyridinyl)propanoate (185 mg, 0.96 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. (107 mg, 34%); LC/MS: MS (ES+) m/e 331 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.20 (s, 3H) 2.26 (s, 3H) 4.02 (s, 2H) 6.12 (s, 1H) 6.98-7.06 (m, 3H) 7.56 (s, 1H) 7.82 (br. s., 1H) 7.81 (d, J=5.31 Hz, 1H) 8.80 (dd, J=4.55, 1.52 Hz, 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-775f7a1f3d1b4d99aebcf631e63f7355
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

Loading…