Water → HCID 178507736, compound

HRID 2236673Notes

Reaction equation

HRID 2236673 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.Cl.[NH2:19][C:20]1[CH:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[C:22]([OH:28])[C:21]=1[OH:29].CCN(CC)CC.O>CN(C)C=O>[NH2:19][C:20]1[CH:25]=[C:24]([CH:23]=[C:22]([OH:28])[C:21]=1[OH:29])[CH2:26][NH:27]/[CH:14]=[C:5]1\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]2[C:4]\1=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dioneHCID 68698883HCID 68698883, compound

Product 1

HCID 178507736HCID 178507736, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (124 mg, 0.44 mmol), 3-amino-5-aminomethyl-benzene-1,2-diol dihydrochloride salt (100 mg, 0.44 mmol) and Et3N (0.15 mL, 1.1 mmol) in N,N-dimethylformamide (DMF) (5 mL) is stirred at 25° C. for 24 hours. Water (10 mL) is added to the reaction mixture. The resulting solid is filtered and washed with water. The crude solid is purified by HPLC, eluting with 20% CH3CN/H2O to 100% CH3CN over 30 minutes to give 51 mg (22%) of the title compound as a brown solid. HRMS (ESI) m/z calcd for C17H14BrN3O4 (M+H)+ 404.02405. found: 404.02336.

Workup

  1. filtrationThe resulting solid is filtered
  2. washwashed with water
  3. customThe crude solid is purified by HPLC
  4. washeluting with 20% CH3CN/H2O to 100% CH3CN over 30 minutes

Sources & evidence

ORD record
ord-19f4172154014cdc9db5976f99f180e4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…