Ethylenediamine → 2-(2-Aminoethyl)-1,3-di-Boc-guanidine

HRID 1061718Notes

Reaction equation

HRID 1061718 reaction equation
[C:1]([NH:8][C:9]([N:18]1[CH:22]=[CH:21]C=N1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N)C[NH2:25]>C1COCC1>[C:11]([NH:10][C:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[N:18][CH2:22][CH2:21][NH2:25])([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

Product 1

HCID 109903042-(2-Aminoethyl)-1,3-di-Boc-guanidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With continued reference to Scheme J, a solution of the N,N′-bis-(Boc)-1H-Pyrazole-1-carboxamidine (2 g, 6.45 mmol) in THF (50 ml) was added dropwise to ethylene diamine (4 ml, 59.6 mmol) in THF (100 ml). After 30 min of mixing at room temperature solvent was evaporated then toluene (100 ml) was added and evaporated in order to remove remaining traces of the ethylene diamine. The resulting product (Compound XXIV) was treated immediately according to scheme K since it decomposes at room temperature. 1H NMR (CDCl3, 400 MHz) δ 1.40-1.61 (m, 18H), 2.87-2.90 (t, 2H,), 3.47-3.50 (m, 2H), 6.31-6.34 (t, 0.61H), 7.61-7.62 (d, 1H), 8.45-8.66 (broad s).

Workup

  1. additionAfter 30 min of mixing at room temperature solvent
  2. customwas evaporated
  3. additiontoluene (100 ml) was added
  4. customevaporated in order
  5. customto remove
  6. additionThe resulting product (Compound XXIV) was treated immediately
  7. customdecomposes at room temperature

Sources & evidence

ORD record
ord-d313c438859e41a984e2dbc8b1c7a778
Source dataset
uspto-grants-2005_11
Patent number
US06960594B2

Reaction notes

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