Hydrochloric Acid → HCID 20812187, compound

HRID 895596Notes

Reaction equation

HRID 895596 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@H:10]([OH:20])[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].[OH-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@:10]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([OH:20])[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 69552815(8S,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 20812187HCID 20812187, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2 g of (8S,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one, 1 g of Adogen 464, 7 ml of 50% strength aqueous sodium hydroxide solution and 0.8 ml of benzyl bromide are intensively stirred at room temperature for 16 h in 10 ml of dichloromethane. The mixture is then adjusted to pH 7 using ½ conc. aqueous hydrochloric acid with cooling and extracted three times with 100 ml of dichloromethane each time, and the organic phases are combined and washed twice with a little water. After stripping off the volatile components in vacuo, the residue obtained is chromatographed on silica gel (eluent: dichloromethane/methanol 100/3). 1.2 g of the title compound are obtained as yellowish crystals of melting point 248-51° C.

Workup

  1. temperaturewith cooling
  2. extractionextracted three times with 100 ml of dichloromethane each time
  3. washwashed twice with a little water
  4. customthe residue obtained
  5. customis chromatographed on silica gel (eluent: dichloromethane/methanol 100/3)

Sources & evidence

ORD record
ord-44138e8afdca44b5be25cfe9bc8d12b7
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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