Isonicotinic Acid → HCID 15289251, compound

HRID 1707630Notes

Reaction equation

HRID 1707630 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl.CCOC(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]([N:35]2[CH2:34][CH2:33][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:37][CH2:36]2)=[O:9])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15289251HCID 15289251, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A sample of 4-pyridinecarboxylic acid (1.32 g, 10.7 mmol) was dissolved in 50 mL of CH2Cl2. To this solution under N2 was added N-methylmorpholine (1.21 mL, 11.0 mmol) before it was cooled to -78° C. and isobutylchloroformate (1.39 mL, 10.7 mmol) was added. The reaction was allowed to warm to 0° C. and stirred at this temperature for 30 minutes before it was cooled again to -78° C. and t-butyloxycarbonyl piperazine (2.0 g, 10.7 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 18 hours. All solvent was removed under reduced pressure to give a residue that was dissolved in EtOAc, washed with saturated NaHCO3 and brine, and dried (Na2SO4). After all solvent was removed in vacuo, the residue was chromatographed to generate 1.3 g of the title compound.

Workup

  1. temperatureto warm to 0° C.
  2. temperaturewas cooled again to -78° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for 18 hours
  5. customAll solvent was removed under reduced pressure
  6. customto give a residue that
  7. washwashed with saturated NaHCO3 and brine
  8. dry with materialdried (Na2SO4)
  9. customAfter all solvent was removed in vacuo
  10. customthe residue was chromatographed

Sources & evidence

ORD record
ord-dec968600cd248a1979a1ff897fceac8
Source dataset
uspto-grants-1994_10
Patent number
US05354747

Reaction notes

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