Water → N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]-N-methyl-beta-alanine methyl ester

HRID 1164829Notes

Reaction equation

HRID 1164829 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][NH:15][CH3:16])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.Br[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][N: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])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 198618223,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide

Product 1

HCID 19863358N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]-N-methyl-beta-alanine methyl esterYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.44 g (10.0 mmol) of 3,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide, 1.67 g (10.0 mmol) of methyl 3-bromopropionate and 1.38 g (10.0 mmol) of potassium carbonate was stirred in 20 ml of DMF for 18 hours at ambient temperature. Water (100 ml) was added and the solid was filtered and air dried. Crystallization from ethanol provided 2.1 g (6.34 mmol, 63%) of N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]-N-methyl-beta-alanine methyl ester as white crystals; mp 136.5°-137° C.

Workup

  1. filtrationthe solid was filtered
  2. customair dried
  3. customCrystallization from ethanol

Sources & evidence

ORD record
ord-728abec3d9cd481694b909a03ca98496
Source dataset
uspto-grants-1990_03
Patent number
US04906633

Reaction notes

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