Acetic Acid → HCID 49846145, compound

HRID 1930144Notes

Reaction equation

HRID 1930144 reaction equation
[OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]CC)=[O:26])=[CH:20][C:19]=3[CH3:30])=[CH:14][CH:13]=2)[C:9]([CH3:31])=[N:8][C:7]=1[CH3:32])(=[O:5])[NH2:4].C(O)(=O)C>C(O)(C)(C)C.C(O)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=3[CH3:30])=[CH:14][CH:13]=2)[C:9]([CH3:31])=[N:8][C:7]=1[CH3:32])(=[O:5])[NH2:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 59627681HCID 59627681, compound2×

Product 1

HCID 49846145HCID 49846145, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
45 °C

Procedure

Powdered potassium hydroxide (65.9 mg, 1.17 mmol) was added in one portion to ethyl 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-methylbiphenyl-4-yl)acetate (Intermediate 12-1; 79 mg, 0.20 mmol) in tert-butanol (2 mL) at 45° C. under nitrogen. The resulting solution was stirred at 45° C. for 1 hour. The mixture was treated with acetic acid (0.090 mL, 1.57 mmol) in ethanol (1 mL) and stirred at room temperature for 10 minutes. The mixture was then evaporated under vacuum to give an off white solid. This was triturated with water (10 mL), filtered off and washed with water (10 mL), before drying under vacuum to give desired product.

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. customThe mixture was then evaporated under vacuum
  3. customto give an off white solid
  4. customThis was triturated with water (10 mL)
  5. filtrationfiltered off
  6. washwashed with water (10 mL)
  7. custombefore drying under vacuum

Sources & evidence

ORD record
ord-0b328406f81e4bf09ea47663ea75ad28
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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