Triethylamine → N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]glycine methyl ester

HRID 1164832Notes

Reaction equation

HRID 1164832 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][NH2:15])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.Br[CH2:17][C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:21][O:20][C:18](=[O:19])[CH2:17][NH:15][CH2:14][CH2:13][NH:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 151481293,5-Diamino-N-(2-aminoethyl)-6-chloropyrazine-2-carboxamide

Product 1

HCID 19863354N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]glycine methyl esterYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13.7 g (59.4 mmol) of 3,5-diamino-6-chloro-N-(2-aminoethyl)pyrazine-2-carboxamide, 3.03 g (19.8 mmol) of methyl bromoacetate and 2.0 g (19.8 mmol) of triethylamine was stirred overnight in 250 ml of tetrahydrofuran at ambient temperature. The solvent was evaporated and the residue was chromatographed on silica gel (300 g) using 3.5:96.5 (v/v) methanol:methylene chloride as eluent. There was obtained 4.45 g (14.7 mmol, 74%) of N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]glycine methyl ester as a white powder; mp 145°-146.5° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on silica gel (300 g)

Sources & evidence

ORD record
ord-db127294173c4767af47d9129e4735ac
Source dataset
uspto-grants-1990_03
Patent number
US04906633

Reaction notes

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