Ethylenediamine → HCID 178456500, compound

HRID 248089Notes

Reaction equation

HRID 248089 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([C:17]3[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23](O)=[O:24])=[CH:19][CH:18]=3)[CH2:15][CH3:16])[NH:8][C:7]=2[N:6]([CH2:28][CH2:29][CH3:30])[C:5]1=[O:31])[CH2:2][CH3:3].ON1C(=O)CCC1=O.Cl.CN(C)CCCN=C=NCC.[CH2:52]([NH2:55])[CH2:53][NH2:54]>CN(C)C=O.CO.[Cl-].[Na+].O>[NH2:54][CH2:53][CH2:52][NH:55][C:23](=[O:24])[CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([CH:14]([C:9]2[NH:8][C:7]3[N:6]([CH2:28][CH2:29][CH3:30])[C:5](=[O:31])[N:4]([CH2:1][CH2:2][CH3:3])[C:12](=[O:13])[C:11]=3[N:10]=2)[CH2:15][CH3:16])=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178456504HCID 178456504, compound

Product 1

HCID 178456500HCID 178456500, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Dissolve 2-[4-[1-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid (720 mg, 1.68 mmol) in dimethylformamide (10 mL) and treat with N-hydroxysuccinimide (192 mg, 1.68 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (676 mg, 3.53 mmol). Stir for 1.5 hours and add to a solution of ethylenediamine (10 mL of a 10% solution in methanol). Stir for 1.5 hours, pour into brine (300 mL) and extract with ethyl acetate (3×200 mL) and chloroform (3×300 mL). Dry (MgSO4) and evaporate the solvent in vacuo. Purify by radial chromatography (5→10→20% methanol chloroform with 1% ammonium hydroxide) and recrystallize (10% isopropanol/pentane to give the title compound (51 mg) as a white solid; mp 139-40° C.

Workup

  1. stirringStir for 1.5 hours
  2. extractionextract with ethyl acetate (3×200 mL) and chloroform (3×300 mL)
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. customPurify by radial chromatography (5→10→20% methanol chloroform with 1% ammonium hydroxide)
  6. customrecrystallize (10% isopropanol/pentane

Sources & evidence

ORD record
ord-ed131d269b85466a99f4ab65b08a3ab6
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

Loading…