Acetonitrile → HCID 11382630, compound

HRID 2377797Notes

Reaction equation

HRID 2377797 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3([C:21]#[CH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:10]([CH3:13])[N:11]=2)[C:6](=[O:23])[C:5]([C:24]([O:26]CC)=[O:25])=[CH:4]1)[CH3:2].[OH-].[Na+].C(#N)C>O1CCOCC1.O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3([C:21]#[CH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:10]([CH3:13])[N:11]=2)[C:6](=[O:23])[C:5]([C:24]([OH:26])=[O:25])=[CH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 6342Acetonitrile2×HCID 14798Sodium HydroxideHCID 11406408HCID 11406408, compound

Product 1

HCID 11382630HCID 11382630, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1-ethyl-6-(1-ethynylcyclohexylamino)-7-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate (10 mg) was dissolved in 5 ml of dioxane, 2.5 equivalents of a 1 N NaOH solution were added, and the mixture was heated at 60° C. for 4 h. Removal of the solvent in vacuo was followed by chromatography on an HPLC system to purify the product. The pure product was isolated from the reaction solution by chromatography on an HPLC system. This entailed use of a Merck Purospher-RP18 column and an acetonitrile:water mixture as eluent; the initial acetonitrile content was 15% and rose to 95% over the course of 20 minutes.

Workup

  1. customRemoval of the solvent in vacuo
  2. customto purify the product
  3. customThe pure product was isolated from the reaction solution by chromatography on an HPLC system
  4. customrose to 95% over the course of 20 minutes

Sources & evidence

ORD record
ord-6be038b02a904dff9dfca22502a68590
Source dataset
uspto-grants-2008_12
Patent number
US07470706B2

Reaction notes

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