Acetic Acid → HCID 67417398, compound

HRID 1951400Notes

Reaction equation

HRID 1951400 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[C:13]([CH:15]=[C:16]([O-])[C:17]([F:20])([F:19])[F:18])#[N:14].[Na+].[NH2:23][C:24]1[CH:29]=[CH:28][NH:27][C:26](=[O:30])[CH:25]=1.C(O)(=O)C>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:25]3[C:26](=[O:30])[NH:27][CH:28]=[CH:29][C:24]=3[NH:23][C:16]([C:17]([F:20])([F:19])[F:18])=[C:15]2[C:13]#[N:14])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 166592514-Formyl-3-methoxybenzonitrileHCID 75611571HCID 75611571, compound

Product 1

HCID 67417398HCID 67417398, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

500 mg (3.1 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 493 mg (3.1 mmol) of sodium 1-cyano-3,3,3-trifluoroprop-1-en-2-olate, 341 mg (3.1 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 266 μl (4.65 mmol) of acetic acid in 40 ml of isopropanol and heated under reflux under argon for 12 h. After cooling, the solution is concentrated, and the residue is again stirred in 45 ml of acetic acid under reflux overnight. The solution is cooled and then concentrated, and the residue is purified by preparative HPLC. 392 mg (34% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureAfter cooling
  4. concentrationthe solution is concentrated
  5. temperatureunder reflux overnight
  6. temperatureThe solution is cooled
  7. concentrationconcentrated
  8. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-cc92dc803bb74c3ca257efbb57d01c57
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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