Ethylenediamine → HCID 58955137, compound

HRID 1992519Notes

Reaction equation

HRID 1992519 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15](OS(C)(=O)=O)[CH2:14]1.[CH2:23]([NH2:26])[CH2:24][NH2:25]>O>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([NH:25][CH2:24][CH2:23][NH2:26])[CH2:14]1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 58955142HCID 58955142, compound

Product 1

HCID 58955137HCID 58955137, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methanesulfonic acid 1-(6-methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl ester (1.96 g, 6.1 mmol) was heated to 100° C. in ethylene diamine (10 mL, 150 mmol) overnight. The reaction mixture was cooled, diluted with water and extracted 4× with a solution of 10% isopropanol in chloroform. The combined organic layers were washed with brine, dried over magnesium sulfate, and purified by column chromatography (silica, 10% MeOH in chloroform) to afford the title coompound as a white solid (1.3 g, quantitative yield as an adduct of two moles of water): LC/MS m/z 288 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted 4× with a solution of 10% isopropanol in chloroform
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. custompurified by column chromatography (silica, 10% MeOH in chloroform)

Sources & evidence

ORD record
ord-fcee6ce558594867a28b3d0ca6b88a7d
Source dataset
uspto-grants-2010_01
Patent number
US07648984B2

Reaction notes

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