Triethylamine → HCID 59299897, compound

HRID 2236643Notes

Reaction equation

HRID 2236643 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[CH:14]OC)[C:6](=[O:17])[N:5]1[C:18](=[O:20])[CH3:19])(=[O:3])[CH3:2].Cl.[NH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][CH3:32])=[C:28]([OH:30])[CH:29]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)/[C:7](=[CH:14]/[NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:31][CH3:32])=[C:28]([OH:30])[CH:29]=2)/[C:6](=[O:17])[N:5]1[C:18](=[O:20])[CH3:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 686929551,2-diacetyl-4-methoxymethylene-1,4-dihydro-2H-cinnolin-3-one

Product 1

HCID 59299897HCID 59299897, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,2-diacetyl-4-methoxymethylene-1,4-dihydro-2H-cinnolin-3-one (0.18 g, 0.66 mmol) and 5-(aminomethyl)-2-methoxyphenol hydrochloride (0.13 g, 0.66 mmol) in tetrahydrofuran (5 mL) is added triethylamine (0.21 mL). After the addition of a few drops of N,N-dimethylformamide, the reaction mixture is stirred for five days at room temperature. The solvent is then evaporated under reduced pressure to give a maroon oil, which is then purified by via semi-preparative HPLC (Prodigy ODS3 column, 40% MeCN/60% water/0.01% trifluoroacetic acid to 70% acetonitrile over 1 hour at 10 mL/min) to give (4Z)-1,2-diacetyl-4-{[(3-hydroxy-4-methoxybenzyl)amino]methylene}-1,4-dihydrocinnolin-3(2H)-one (0.14 g, 54%) as a straw-colored foam, which is crushed to a powder.

Workup

  1. customThe solvent is then evaporated under reduced pressure
  2. customto give a maroon oil, which
  3. customis then purified by via semi-preparative HPLC (Prodigy ODS3 column, 40% MeCN/60% water/0.01% trifluoroacetic acid to 70% acetonitrile over 1 hour at 10 mL/min)

Sources & evidence

ORD record
ord-ecbd2f37a0604ff8867847bb28be1f0e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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