(4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione → HCID 178440613, compound

HRID 2236896Notes

Reaction equation

HRID 2236896 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])/[C:8]/2=[CH:17]/OC)([CH3:4])([CH3:3])[CH3:2].[NH2:20][CH2:21][C:22]1[CH:27]=[C:26]([OH:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][N:23]=1>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])[C:8]2=[CH:17][NH:20][CH2:21][C:22]1[CH:27]=[C:26]([OH:28])[C:25]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:24][N:23]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 42625173(4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 1785102552-Aminomethyl-5-phenyl-pyridin-4-ol

Product 1

HCID 178440613HCID 178440613, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 40.0 mg (0.154 mmol) of (4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (based on a sample that is 39% pure by weight), is dissolved in N,N-dimethylformamide (3 mL), followed by the addition of 31 mg (0.154 mmol) of 2-aminomethyl-5-phenyl-pyridin-4-ol. All solids dissolved and after the mixture is stirred at room temperature for 2 hours, the solution is evaporated to dryness in vacuo, treated with acetonitrile, filtered and washed several times with fresh acetonitrile and dried to give 44 mg of the title compound as a pink solid (66% yield); mp 195-218° C. dec, MS data ES(+) 428.4 m/e.

Workup

  1. dissolutionAll solids dissolved
  2. customthe solution is evaporated to dryness in vacuo
  3. additiontreated with acetonitrile
  4. filtrationfiltered
  5. washwashed several times with fresh acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-b6efc3f2046b4cc3adc5b5620c36abb5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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