Water → HCID 178458419, compound

HRID 2236618Notes

Reaction equation

HRID 2236618 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH3:13])=[C:7]([OH:9])[CH:8]=1.C(N(CC)CC)C.[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[NH:27][C:26](=[O:33])/[C:25]/2=[CH:34]/OC.O>CN(C)C=O>[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[NH:27][C:26](=[O:33])/[C:25]/2=[CH:34]\[NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH3:13])=[C:7]([OH:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 219043645-(Aminomethyl)-2-propoxyphenolHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178458419HCID 178458419, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the general procedure of example 129, an amount of 100 mg (0.55 mmol) of 5-(aminomethyl)-2-propoxyphenol is dissolved in N,N-dimethylformamide (5 mL). 228 μl (1.65 mmol) of triethylamine is added followed by 171 mg (0.607 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione. After the mixture is stirred at room temperature for 30 min, water (3 mL) is added and the reaction mixture is stirred for 3 hours. The precipitate is filtered and washed several times with anhydrous ether. The crude solid is then purified by high performance liquid chromatography to give 67 mg of a white solid. MS (ESI) m/z 430.8 (M+1).

Workup

  1. stirringthe reaction mixture is stirred for 3 hours
  2. filtrationThe precipitate is filtered
  3. washwashed several times with anhydrous ether
  4. customThe crude solid is then purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-46d373f5ee134ca6bf371942d47ee002
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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