N,N-Bis(2-aminoethyl)methylamine → HCID 22152287, compound

HRID 1111329Notes

Reaction equation

HRID 1111329 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH3:8])[CH2:5][CH2:6][NH2:7].[NH2:9][C:10]1[C:11]([C:18](N2C=CN=C2)=[O:19])=[N:12][C:13]([Cl:17])=[C:14]([NH2:16])[N:15]=1>O1CCCC1>[NH2:9][C:10]1[C:11]([C:18]([NH:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][NH2:7])[CH3:8])=[O:19])=[N:12][C:13]([Cl:17])=[C:14]([NH2:16])[N:15]=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 22152287HCID 22152287, compoundYield 69,354.797%

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 a method of obtaining this compound) in 700 ml of tetrahydrofuran was added 88.6 g (0.372 mmol) of 1-(3,5-diamino-6-chloropyrazinoyl)imidazole in 10 portions over 1 5 h. After 1 h 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]-6chloropyrazinecarboxamide. A sample was filtered through a pad of silica gel and eluted with 5:95 (v/v) methanol:methylene chloride saturated with ammonia gas mp 138°-139.5° C.

Workup

  1. filtrationAfter 1 h 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-08ea98766d7844d98b7ac2d8ac30bbb8
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

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