(3,5-diamino-6-chloropyrazin-2-yl)(1H-imidazol-1-yl)methanone → 3,5-diamino-N-[2-[(2-aminoethyl)propylamino]ethyl]-6-chloropyrazinecarboxamide

HRID 1710006Notes

Reaction equation

HRID 1710006 reaction equation
[NH2:1][C:2]1[C:3]([C:10](N2C=CN=C2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:17][CH2:18][CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][NH2:23]>O1CCCC1>[NH2:1][C:2]1[C:3]([C:10]([NH:17][CH2:18][CH2:19][N:20]([CH2:21][CH2:22][NH2:23])[CH2:24][CH2:25][CH3:26])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

4

Reactant 2

HCID 13020010(3,5-diamino-6-chloropyrazin-2-yl)(1H-imidazol-1-yl)methanoneHCID 14122862N-(2-aminoethyl)-N-propyl-1,2-ethanediamine

Product 1

HCID 542301853,5-diamino-N-[2-[(2-aminoethyl)propylamino]ethyl]-6-chloropyrazinecarboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 23.87 g (100.0 mmol) of 1-(3,5-diamino-6-chloropyrazinoyl)imidazole and 58.51 g (300.0 mmol) of N-(2-aminoethyl)-N-propyl-1,2-ethanediamine in 250 ml of tetrahydrofuran was stirred at ambient temperature overnight. The solvent and excess triamine were evaporated and the residue chromatographed on silica gel (150 g) using 1.5:98.5 (v/v) methanol:tetrahydrofuran saturated with ammonia gas as eluent. There was obtained 24.64 g (78.0 mmol, 78%) of 3,5-diamino-N-[2-[(2-aminoethyl)propylamino]ethyl]-6-chloropyrazinecarboxamide as a yellow solid; mp 91°-94° C.

Workup

  1. customThe solvent and excess triamine were evaporated
  2. customthe residue chromatographed on silica gel (150 g)

Sources & evidence

ORD record
ord-6fcd42492a0b403cac33c043a6b39e8e
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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