Hydrochloric Acid → HCID 90402494, compound

HRID 576689Notes

Reaction equation

HRID 576689 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C:10]2=[N:9][N:8]=1.Cl.CCO>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][NH:14][CH2:15][C:10]2=[N:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 90402528tert-butyl 3-(pyrazin-2-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Product 1

HCID 90402494HCID 90402494, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(pyrazin-2-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (9.3 g, 30 mmol) in DCM (100 mL) was added 1.25M HCl in EtOH (30 mL, 37.5 mmol). After 3 h, the reaction mixture was concentrated, and the resulting solid was purified by chromatography (SiO2; 10% MeOH in DCM) to provide the desired product as a white solid (3.7 g, 61%). MS (ESI): mass calcd. for C9H10N6, 202.1; m/z found, 203.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 9.35 (d, J=1.4 Hz, 1H), 8.72 (dd, J=2.5, 1.6 Hz, 1H), 8.66 (d, J=2.6 Hz, 1H), 4.50 (t, J=5.6 Hz, 2H), 4.22 (s, 2H), 3.24 (t, J=5.6 Hz, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe resulting solid was purified by chromatography (SiO2; 10% MeOH in DCM)

Sources & evidence

ORD record
ord-6ed73f49f6b84e3f9396abbe437a3a13
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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