Water → HCID 178458507, compound

HRID 2236676Notes

Reaction equation

HRID 2236676 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]([O:31][CH2:32][CH2:33][CH3:34])[C:23]([O:27][CH2:28][CH2:29][CH3:30])=[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:21]=[C:22]([O:31][CH2:32][CH2:33][CH3:34])[C:23]([O:27][CH2:28][CH2:29][CH3:30])=[C:24]([OH:26])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dioneHCID 68693921HCID 68693921, compound

Product 1

HCID 178458507HCID 178458507, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (110 mg, 0.39 mmol), 5-aminomethyl-2,3-dipropoxy-phenol hydrochloride salt (93 mg, 0.39 mmol) and Et3N (112 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 170 mg (91%) of the title compound as a tan powder. HRMS (ESI) m/z calcd for C23H25BrN2O5 (M+H)+1 489.10196. found: 489.10078.

Workup

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

Sources & evidence

ORD record
ord-44a164661f4b449eb54790877655ac95
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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