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Dimethylamine → 4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

HRID 1817344
Notes
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Reaction equation

HRID 1817344 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23](O)=[O:24])=[N:5][CH:4]=1.C1[CH:31]=[N:30][C:29]2N(O)N=NC=2C=1.CNC>C1COCC1.C(Cl)CCl>[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([N:30]([CH3:31])[CH3:29])=[O:24])=[N:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 674DimethylamineHCID 181649HOAtHCID 690648344-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Product 1

HCID 690697114-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-Dichloroethane
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A 250 mL THF suspension of 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid (11.0 g), 8.0 g EDC, 5.7 g HOAT, and 11.2 mL TEA was stirred at room temperature for 20 minutes, followed by addition of 45 mL of a 2M THF solution of dimethylamine and then stirring for 1.5 hours. The reaction was quenched with 200 mL of 1N aq HCl and stirred vigorously for 30 minutes. After concentrating in vacuo until an oil formed on the water layer, 200 mL chloroform was added. The water layer was washed again with chloroform then the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to pure product by HPLC/MS and NMR.

Workup

  1. stirringstirring for 1.5 hours
  2. customThe reaction was quenched with 200 mL of 1N aq HCl
  3. stirringstirred vigorously for 30 minutes
  4. concentrationAfter concentrating in vacuo until an oil
  5. customformed on the water layer, 200 mL chloroform
  6. additionwas added
  7. washThe water layer was washed again with chloroform
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to pure product by HPLC/MS and NMR

Sources & evidence

ORD record
ord-b1c82edb267f49a9ab68a899cff26038
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598264B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes