Ethylenediamine → N-(2-Aminoethyl)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]-acetamide

HRID 248090Notes

Reaction equation

HRID 248090 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([CH3:27])[CH2:15][C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](O)=[O:23])=[CH:18][CH:17]=3)[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.C(Cl)(Cl)Cl>[NH2:54][CH2:53][CH2:52][NH:55][C:22](=[O:23])[CH2:21][O:20][C:19]1[CH:25]=[CH:26][C:16]([CH2:15][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)[CH3:27])=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178456503HCID 178456503, compound

Product 1

HCID 178456499N-(2-Aminoethyl)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]-acetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve (+)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid (0.28 g, 0.65 mmol) in dimethylformamide (10 mL) and treat with N-hydroxysuccinimide (0.074 g, 0.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.262 g, 1.37 mmol). Stir for 1 hour and add a solution of ethylenediamine (10 mL of a 10% solution in methanol) and stir for 1 hour. Dilute with chloroform (500 mL), wash with 5% sodium carbonate (200 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by radial chromatography (10→20% methanol/chloroform with 1% ammonium hydroxide). Dissolve the purified material in 5% methanol/ethyl ether and treat with ethereal hydrochloric acid. Evaporate the solvent in vacuo and triturate the residue with ethyl ether. Filter the resulting solid and dry to give the title compound (88 mg); [α]d 20 =+75.7° (C=0.96, H2O).

Workup

  1. stirringstir for 1 hour
  2. washwash with 5% sodium carbonate (200 mL)
  3. dry with materialdry (MgSO4)
  4. customEvaporate the solvent in vacuo
  5. custompurify by radial chromatography (10→20% methanol/chloroform with 1% ammonium hydroxide)
  6. dissolutionDissolve the purified material in 5% methanol/ethyl ether
  7. additiontreat with ethereal hydrochloric acid
  8. customEvaporate the solvent in vacuo
  9. customtriturate the residue with ethyl ether
  10. filtrationFilter the resulting solid
  11. customdry

Sources & evidence

ORD record
ord-3f9969aa964b47e399f48e847cbcaf74
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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