(4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione → HCID 178458786, compound

HRID 2236895Notes

Reaction equation

HRID 2236895 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]([O:29][CH2:30][CH2:31][CH3:32])=[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]([O:29][CH2:30][CH2:31][CH3:32])=[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 178458783HCID 178458783, compound

Product 1

HCID 178458786HCID 178458786, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 50.0 mg (0.193 mmol) of (4E)-6-tert-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione, is dissolved in N,N-dimethylformamide (3 mL), followed by the addition of 35 mg (0.193 mmol) of 2-aminomethyl-5-propoxy-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 52 mg of the title compound as a light pink solid (66% yield); mp 162-178° C. dec, MS data ES(+) 410.4 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-c286da46e3254da3af024ab6b5daa07c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…