N,N-Bis(2-aminoethyl)methylamine → 6-chloropyrazine-2-carboxamide

HRID 1165439Notes

Reaction equation

HRID 1165439 reaction equation
NCCN(C)CCN.N[C:10]1[C:11]([C:18]([N:20]2C=CN=C2)=[O:19])=[N:12][C:13]([Cl:17])=[C:14](N)[N:15]=1>O1CCCC1>[Cl:17][C:13]1[N:12]=[C:11]([C:18]([NH2:20])=[O:19])[CH:10]=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 430288N,N-Bis(2-aminoethyl)methylamineHCID 13020010(3,5-diamino-6-chloropyrazin-2-yl)(1H-imidazol-1-yl)methanone

Product 1

HCID 12825296-chloropyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 84.0 g (0.744 mol) of N-(2-aminoethyl)-N-methyl-1,2-ethanediamine (see U.S. Pat. No. 3,201,472 for an example of how to obtain this material) in 700 ml of tetrahydrofuran was added 88.6 g (0.372 mol) of 1-(3,5-diamino-6-chloropyrazinoyl)imidazole in 10 portions over 1.5 hours. After 1 hour at ambient temperature the reaction mixture was filtered and concentrated to 300 ml. The solution was added dropwise to 1.4 liters of ether with vigorous stirring. The solid was filtered, washed with ether and dried. There was obtained 74.3 g (0.258 mol, 70%) of 3,5-diamino-N-2-[(2-aminoethyl)methylamino]ethyl]-6-chloropyrazinecarboxamide. A sample was filtered through a pad of silica gel and eluted with 5:95 (v/v) methanol:methylene chloride saturated wth ammonia gas; mp 138°-139.5° C.

Workup

  1. filtrationAfter 1 hour at ambient temperature the reaction mixture was filtered
  2. concentrationconcentrated to 300 ml
  3. additionThe solution was added dropwise to 1.4 liters of ether with vigorous stirring
  4. filtrationThe solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-4087a0faaa5647cf920659a9438cc31b
Source dataset
uspto-grants-1990_03
Patent number
US04910202

Reaction notes

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