2-Dimethylaminopyridine → HCID 89963068, compound

HRID 338025Notes

Reaction equation

HRID 338025 reaction equation
[CH3:1][N:2]1[C:6]([C@@:7]2([OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[OH:13])=[CH:5][CH:4]=[N:3]1.CN(C1C=CC=CN=1)C.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:6]([C@@:7]23[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[O:13][C:24](=[O:25])[O:14]3)=[CH:5][CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 682631,1'-Carbonyldiimidazole3×HCID 89962992HCID 89962992, compound

Product 1

HCID 89963068HCID 89963068, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the (1S,2S)-1-(1-methyl-1H-pyrazol-5-yl)cyclohexane-1,2-diol (1.21 g, 6.17 mmol) prepared in Example 123c, dimethylaminopyridine (75.3 mg, 0.62 mmol) and carbonyldiimidazole (2.0 g, 12.3 mmol) in toluene (20 mL) was stirred for 3 hours under heated reflux. To the reaction solution, carbonyldiimidazole (1.0 g, 6.17 mmol) was added, and the reaction solution was further stirred for 3 hours under heated reflux. To the reaction solution, carbonyldiimidazole (0.50 g, 3.08 mmol) was further added, and the reaction solution was stirred for 3 hours under heated reflux. After allowing to cool, the reaction solution was vacuum concentrated, and the residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3) to yield the title compound (1.18 g, 86%) as a colorless solid.

Workup

  1. temperatureunder heated
  2. temperaturereflux
  3. temperatureunder heated
  4. temperaturereflux
  5. stirringthe reaction solution was stirred for 3 hours
  6. temperatureunder heated
  7. temperaturereflux
  8. temperatureto cool
  9. concentrationconcentrated
  10. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-b933582f9d3b464bae3b9746ddba6673
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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