4-Methylmorpholine → 11-(3-Chloro-4-fluorobenzyl)-9-hydroxy-2-methyl-3,4,5,6,12,13-hexahydro-2H [1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione

HRID 17995Notes

Reaction equation

HRID 17995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:26])[C:10](=[O:25])[N:11]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH3:24])[C:12]=2[C:16](O)=[O:17])[C:7]1=[O:27].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:26])[C:10](=[O:25])[N:11]3[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[C:16](=[O:17])[C:12]3=2)[C:7]1=[O:27]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669968806-(3-Chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

Product 1

HCID 5469778811-(3-Chloro-4-fluorobenzyl)-9-hydroxy-2-methyl-3,4,5,6,12,13-hexahydro-2H [1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (0.18 g, 0.40 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.08 g, 0.41 mmol), and 1-hydroxy-7-azabenzotriazole (0.07 g, 0.51 mmol), and N-methylmorpholine (0.35 mL, 3.16 mmol) in anhydrous DMF (3 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The residue was purified by reverse phase high pressure liquid chromatography. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was purified by reverse phase high pressure liquid chromatography
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-d594ee25cbc94fa7bfb274c5326d73c6
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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