t-Butyl [2-(5-chloropyrazine-2-carboxamido)ethyl]carbamate → N-(2-aminoethyl)-5-chloropyrazine-2-carboxamide hydrochloride

HRID 34944Notes

Reaction equation

HRID 34944 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:9])=[N:6][CH:7]=1>FC(F)(F)C(O)=O>[ClH:1].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:9]

Participants

3

Reactant 1

HCID 54311956t-Butyl [2-(5-chloropyrazine-2-carboxamido)ethyl]carbamate

Product 1

HCID 13800272N-(2-aminoethyl)-5-chloropyrazine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.6 g of t-butyl [2-(5-chloropyrazine-2-carboxamido)ethyl]carbamate in 6 ml of trifluoroacetic acid was stirred at 20° for 20 minutes. The mixture was thereafter evaporated to dryness on a rotary evaporator, the residue was dissolved in methanol and the solution was treated with hydrogen chloride in methanol (6N). After recrystallization from methanol/diethyl ether there was obtained N-(2-aminoethyl)-5-chloropyrazine-2-carboxamide hydrochloride, m.p. 225°.

Workup

  1. customThe mixture was thereafter evaporated to dryness on a rotary evaporator
  2. dissolutionthe residue was dissolved in methanol
  3. additionthe solution was treated with hydrogen chloride in methanol (6N)
  4. customAfter recrystallization from methanol/diethyl ether there

Sources & evidence

ORD record
ord-7a6837b1c65c4528ac3701d8e083fd59
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

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