1-Methyl-1H-1,2,3-triazole → HCID 118006205, compound

HRID 926528Notes

Reaction equation

HRID 926528 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.C([Li])CCC.[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([C:21](N(OC)C)=[O:22])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]>C1COCC1>[CH3:1][N:2]1[C:6]([C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:12](=[O:14])[CH3:13])[CH2:20][CH2:19]2)=[O:22])=[CH:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 1401191-Methyl-1H-1,2,3-triazoleHCID 187135481-acetyl-N-methoxy-N-methylpiperidine-4-carboxamideHCID 178418339Butyllithium

Product 1

HCID 118006205HCID 118006205, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-methyl-1H-1,2,3-triazole (0.28 g, 3.37 mmol) in dry THF (3 mL) was cooled in a −78° C. bath and n-butyllithium (2.5 M in hexanes, 1.26 mL, 3.15 mmol) was added dropwise over a 20 minute period. The suspension was stirred in the cold bath for 30 minutes and then 1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide (0.74 g, 3.45 mmol, Intermediate 52: step a) dissolved in THF (3 mL) was added dropwise. The resulting suspension was stirred at −78° C. for 5 minutes then warmed to 0° C. and stirred for an additional 30 minutes. The mixture was warmed to room temperature and stirred for 2.5 hours then quenched with saturated aqueous NH4Cl. The aqueous mixture was extracted with EtOAc (2×). The combined EtOAc extracts were dried over Na2SO4, filtered, concentrated to dryness and chromatographed (EtOAc/DCM) to provide the title compound.

Workup

  1. additionwas added dropwise
  2. stirringThe resulting suspension was stirred at −78° C. for 5 minutes
  3. stirringstirred for an additional 30 minutes
  4. temperatureThe mixture was warmed to room temperature
  5. stirringstirred for 2.5 hours
  6. customthen quenched with saturated aqueous NH4Cl
  7. extractionThe aqueous mixture was extracted with EtOAc (2×)
  8. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customchromatographed (EtOAc/DCM)

Sources & evidence

ORD record
ord-a0172f5256994d1f87f5f238b8c0c969
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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