Acetic Acid → HCID 178451826, compound

HRID 605019Notes

Reaction equation

HRID 605019 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-f8752740dede4490a69a47e3fc01c672
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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