Acetic Acid → HCID 59603027, compound

HRID 1951401Notes

Reaction equation

HRID 1951401 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.[N+:13]([CH2:16][C:17]([CH3:19])=O)([O-:15])=[O:14].[NH2:20][C:21]1[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=1.C(O)(=O)C>C(O)(C)C.CS(C)=O>[CH3:12][O:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH:1]1[C:22]2[C:23](=[O:27])[NH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:17]([CH3:19])=[C:16]1[N+:13]([O-:15])=[O:14])[C:7]#[N:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 662962-Propanone, 1-nitro-HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 59603027HCID 59603027, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Procedure

688 mg (4.26 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 440 mg (4.26 mmol) of 1-nitroacetone, 470 mg (4.26 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 367 μl (6.40 mmol) of acetic acid in 10 ml of isopropanol and heated under reflux under argon for 12 h. After cooling, DMSO (5 ml) is added and the reaction solution is purified directly by preparative HPLC. 41 mg (2% of theory) of the title compound are obtained as a brown solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureAfter cooling
  4. customthe reaction solution is purified directly by preparative HPLC

Sources & evidence

ORD record
ord-9578d1295784400e89030e9b406cc5dc
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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