Water → HCID 178493866, compound

HRID 2236674Notes

Reaction equation

HRID 2236674 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14]OC.Cl.[NH2:18][CH2:19][C:20]1[CH:21]=[C:22]([OH:29])[C:23]([O:27][CH3:28])=[C:24]([OH:26])[CH:25]=1.CCN(CC)CC.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:18][CH2:19][C:20]1[CH:25]=[C:24]([OH:26])[C:23]([O:27][CH3:28])=[C:22]([OH:29])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dioneHCID 68697756HCID 68697756, compound

Product 1

HCID 178493866HCID 178493866, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (89 mg, 0.32 mmol), 5-aminomethyl-2-methoxy-benzene-1,3-diol hydrochloride salt (66 mg, 0.32 mmol) and Et3N (111 μL, 0.8 mmol) in N,N-dimethylformamide (DMF) (2 mL) is stirred at 25° C. for 24 hours. H2O (10 mL) is added to the reaction mixture. The resulting precipitate is filtered, washed with H2O and dried in vacuo to give 144 mg of the title compound as a beige powder. HRMS (ESI) m/z calcd for C18H15BrN2O5 (M+H)+1 419.02371. found: 419.02294.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with H2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-26762965f10940ea91cba91c0f626488
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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