Acetic Acid → HCID 178451826, compound

HRID 1678766Notes

Reaction equation

HRID 1678766 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[N:8].C[O-].[Na+].[NH:12]([C:14]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=O)[NH2:13].C(O)(=O)C>CO>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[NH:13][N:12]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73172PyrazinecarbonitrileHCID 10942334Sodium MethoxideHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 178451826HCID 178451826, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of pyrazinecarbonitrile (2.0 g, 19 mmol) in methanol (20 mL) was treated with sodium methoxide in methanol (25 wt %, 1.3 mL, 5.7 mmol) at room temperature. After 30 minutes, a solution of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (4.6 g, 19 mmol) in methanol (20 mL) was added and the reaction was heated to reflux for 19 hours. The reaction mixture was concentrated, dissolved in ethoxyethanol (50 mL) and heated to reflux for 22 hours. The reaction was cooled to room temperature, quenched with acetic acid (0.38 mL, 6.6 mmol) and concentrated. The residue was suspended in ether and filtered to give tert-butyl 4-(5-pyrazin-2-yl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate as a solid. HRMS (M+H+): observed=331.1876, calculated=331.1877; 1H NMR (400 MHz, CD3OD): δ 9.29 (d, J=1.6 Hz, 1H), 8.70 (dd, J=2.4, 1.6 Hz, 1H), 8.64 (d, J=2.4 Hz, 2H), 4.19-4.15 (m, 2H), 3.15-3.09 (m, 1H), 2.97 (m, 2H), 2.07-2.03 (m, 2H), 1.84-1.75 (m, 2H), 1.48 (s, 9H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 19 hours
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in ethoxyethanol (50 mL)
  5. temperatureheated
  6. temperatureto reflux for 22 hours
  7. concentrationconcentrated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5abbc2c773ab4ebeb26a3ccd1120cd64
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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