Hydrochloric Acid → HCID 86656623, compound

HRID 882886Notes

Reaction equation

HRID 882886 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 86656624HCID 86656624, compound

Product 1

HCID 86656623HCID 86656623, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ((R)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester (0.65 g, 1.74 mmol) in 1,4-dioxane (15 mL) is added HCl (30 mL of a 4 M solution in 1,4-dioxane, 120 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 ether layer is decanted and the product is dissolved in minimal 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. [M+H]+ 273.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe yellow solid obtained
  3. customis triturated with diethyl ether
  4. customthe ether layer is decanted
  5. dissolutionthe product is dissolved in minimal 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-10227b19d5a44b5ab903a2b8675e1111
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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