Potassium Carbonate → HCID 91413405, compound

HRID 1187407Notes

Reaction equation

HRID 1187407 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]2[N:23]=[N:24][N:25]=[C:17]2[C:16]=1[NH:26][C:27](=O)[CH2:28][O:29][CH2:30][CH3:31])(=O)C>C(O)C.O>[CH2:30]([O:29][CH2:28][C:27]1[N:14]([CH2:13][CH2:12][CH2:11][OH:10])[C:15]2[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]3[N:23]=[N:24][N:25]=[C:17]3[C:16]=2[N:26]=1)[CH3:31]

Participants

4

Reactant 2

HCID 11430Potassium Carbonate3×HCID 69506275HCID 69506275, compound

Product 1

HCID 91413405HCID 91413405, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 6 M potassium carbonate (0.9 mL, 5.2 mmmol) was added to a solution of crude 3-({8-[(ethoxyacetyl)amino]-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl}amino)propyl acetate from Part C in 3:1 ethanol/water (12 mL) at room temperature. The solution was stirred for 3 days, then was heated to 80° C. More 6 M potassium carbonate (3 mL) was added after 1 day. After another day, 6 M potassium carbonate (5 mL) was added again. The temperature was increased to 85° C. and stirring was continued one more day. The solvent was removed under reduced pressure and the residue was partitioned between chloroform (100 mL) and saturated aqueous sodium bicarbonate (30 mL). The layers were separated and the aqueous layer was extracted with chloroform (3×20 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (2>20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 0.35 g of 3-[8-(ethoxyrnethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]propan-1-ol as a white solid.

Workup

  1. waitAfter another day
  2. temperatureThe temperature was increased to 85° C.
  3. stirringstirring
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between chloroform (100 mL) and saturated aqueous sodium bicarbonate (30 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with chloroform (3×20 mL)
  8. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (2>20 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7fe74ecba844c0492c8a7a4a4c84187
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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