Hydrochloric Acid → 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

HRID 882905Notes

Reaction equation

HRID 882905 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15])[CH2:9][CH2:10][CH3:11])(C)(C)C.Cl>O1CCOCC1>[ClH:24].[NH2:7][C@@H:8]([CH2:9][CH2:10][CH3:11])[CH2:12][NH:13][C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86651887((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ((S)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester (1.30 g, 3.49 mmol) in 1,4-dioxane (20 mL) is added HCl (50 mL of a 4 M solution in 1,4-dioxane, 200 mmol) and the reaction mixture is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the yellow solid obtained is triturated with diethyl ether; the diethyl ether layer is decanted and the product is dissolved in a minimal volume of MeOH and is precipitated by the addition of diethyl ether. The solvent is decanted and the resulting solid is dried under vacuum to afford the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe yellow solid obtained
  3. customis triturated with diethyl ether
  4. customthe diethyl ether layer is decanted
  5. dissolutionthe product is dissolved in a minimal volume of MeOH
  6. customis precipitated by the addition of diethyl ether
  7. customThe solvent is decanted
  8. customthe resulting solid is dried under vacuum

Sources & evidence

ORD record
ord-53d8a96397104ee6943503b3688f3753
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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