Dimethylformamide → HCID 59299897, compound

HRID 2236961Notes

Reaction equation

HRID 2236961 reaction equation
CO/[CH:3]=[C:4]1\[C:5](=[O:20])[N:6]([C:17](=[O:19])[CH3:18])[N:7]([C:14](=[O:16])[CH3:15])[C:8]2[C:13]\1=[CH:12][CH:11]=[CH:10][CH:9]=2.Cl.[OH:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:26][NH2:27].C(N(CC)CC)C.CN(C)C=O>O1CCCC1>[C:14]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)/[C:4](=[CH:3]/[NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:23]([OH:22])[CH:24]=2)/[C:5](=[O:20])[N:6]1[C:17](=[O:19])[CH3:18])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 162176463-Hydroxy-4-methoxybenzylamine hydrochlorideHCID 59300145(Z)-1,1'-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone

Product 1

HCID 59299897HCID 59299897, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-1,1′-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone (0.18 g, 0.66 mmol) in tetrahydrofuran (5 mL) is added 3-hydroxy-4-methoxybenzylamine hydrochloride (0.13 g, 0.66 mmol). The suspension is treated with triethylamine (0.21 mL) and dimethylformamide (1 mL). The mixture is stirred at room temperature until LC/MS analysis revealed the consumption of the starting materials. Following concentration under reduced pressure, the crude mixture is purified by semi-preparative reverse-phase HPLC, employing a gradient elution from 40% acetonitrile in water with 0.1% trifluoroacetic acid to 70% acetonitrile in water over 60 minutes. The desired fractions were concentrated under reduced pressure to afford 0.14 g of (4Z)-1,2-diacetyl-4-{[(3-hydroxy-4-methoxybenzyl)amino]methylene}-1,4-dihydrocinnolin-3(2H)-one.

Workup

  1. customthe consumption of the starting materials
  2. concentrationconcentration under reduced pressure
  3. customthe crude mixture is purified by semi-preparative reverse-phase HPLC
  4. washa gradient elution from 40% acetonitrile in water with 0.1% trifluoroacetic acid to 70% acetonitrile in water over 60 minutes
  5. concentrationThe desired fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-ace0ac2cd6c648819f0ee836d5823d42
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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