Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → HCID 178488706, compound

HRID 923344Notes

Reaction equation

HRID 923344 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([NH2:13])[NH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])=[CH:18][CH:17]=1>C(O)(=O)C>[CH2:1]([C:8]1[N:9]=[C:10]2[NH:13][C:22]([C:19]3[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=3)=[CH:23][C:24](=[O:25])[N:11]2[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 11166975-benzyl-1H-1,2,4-triazol-3-amine

Product 1

HCID 178488706HCID 178488706, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-benzyl-2H-1,2,4-triazol-3-amine (174 mg, 1.00 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (228 mg, 1.10 mmol, 1.10 equiv) was stirred overnight at 110° C. and then concentrated to dryness. The resulting solid was washed with 5 mL MeOH and collected by filtration. The solid was dissolved in 10 mL of NH4OH (aq.) and filtered. The filtrate was adjusted to pH 6 with HOAc. The resulting solid was collected by filtration and washed with water. The solid was dried to get 26 mg (8%) of 2-benzyl-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. washThe resulting solid was washed with 5 mL MeOH
  3. filtrationcollected by filtration
  4. dissolutionThe solid was dissolved in 10 mL of NH4OH (aq.)
  5. filtrationfiltered
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customThe solid was dried

Sources & evidence

ORD record
ord-fcd9d4c190b549b281954439b899b77a
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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