HCID 59300156, compound → HCID 178458780, compound

HRID 2236857Notes

Reaction equation

HRID 2236857 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([CH3:14])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH3:13])[C:7](=[O:9])[CH:8]=1.CO[CH:17]=[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([I:28])[CH:26]=2)[C:21](=[O:29])[NH:20][C:19]1=[O:30]>CN(C)C=O>[I:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:29])[NH:20][C:19](=[O:30])[C:18]2=[CH:17][NH:1][CH2:2][C:3]1[N:4]([CH3:14])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH3:13])[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 59300156HCID 59300156, compoundHCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione

Product 1

HCID 178458780HCID 178458780, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-1-methyl-5-propoxy-1H-pyridin-4-one (196 mg, 1.0 mmole), 10 mL of N,N-dimethylformamide is stirred, 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (329 mg, 1.0 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, triturated with 5% methanol in chlororform, filtered washed with fresh 5% methanol in chloroform, washed with acetonitrile and dried to give an off-white solid, 124 mg, (24%); m.p. 176-96° C. dec; MS (ES+): m/z 494.0 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. customtriturated with 5% methanol in chlororform
  4. filtrationfiltered
  5. washwashed with fresh 5% methanol in chloroform
  6. washwashed with acetonitrile
  7. customdried
  8. customto give an off-white solid, 124 mg, (24%)

Sources & evidence

ORD record
ord-7e87563e5acd4418b247b94af6e5a92a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…