Hydrochloric Acid → Methyl 2-amino-3-(pyrazine-2-carboxamido)benzoate

HRID 520446Notes

Reaction equation

HRID 520446 reaction equation
Cl.C(OC([N:9](C(OC(C)(C)C)=O)[C:10]1[C:19]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C>CO>[NH2:9][C:10]1[C:19]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58552825Methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate

Product 1

HCID 58552889Methyl 2-amino-3-(pyrazine-2-carboxamido)benzoateYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl gas was bubbled through a solution of methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate 14 (2.8 g, 5.9 mmol) in MeOH (50 ml) for 2 h. The volatiles were removed in vacuo and H2O (20 mL) was added. The pH was adjusted to 7 using aq NaOH and the resulting precipitate was collected by filtration, rinsed with H2O, and dried under vacuum to give 15 (1.37 g, 85% yield).

Workup

  1. customThe volatiles were removed in vacuo and H2O (20 mL)
  2. additionwas added
  3. filtrationthe resulting precipitate was collected by filtration
  4. washrinsed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ae83657fa39745ff91cb120e5eb5db9e
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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