Hydrochloric Acid → HCID 49847246, compound

HRID 1930104Notes

Reaction equation

HRID 1930104 reaction equation
[OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28]C)=[O:27])=[CH:21][C:20]=3[Cl:30])=[C:14]([F:31])[CH:13]=2)[C:9]([CH3:32])=[N:8][C:7]=1[CH3:33])(=[O:5])[NH2:4].Cl>C(O)(C)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:21][C:20]=3[Cl:30])=[C:14]([F:31])[CH:13]=2)[C:9]([CH3:32])=[N:8][C:7]=1[CH3:33])(=[O:5])[NH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59627738HCID 59627738, compound2×

Product 1

HCID 49847246HCID 49847246, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

Powdered potassium hydroxide (111 mg, 1.98 mmol) was added in one portion to methyl 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chloro-2′,6′-difluorobiphenyl-4-yl)acetate (Intermediate 2-1; 295 mg, 0.66 mmol) in tert-butanol (10 mL) at 50° C. The resulting solution was stirred at 50° C. for 45 minutes, 2M HCl (2 mL) was added and the mixture was evaporated to remove the organic solvent. The suspension was collected by filtration, washed with water (50 mL) and air dried to afford 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chloro-2′,6′-difluorobiphenyl-4-yl)acetic acid (220 mg, 77%) as a cream solid.

Workup

  1. customthe mixture was evaporated
  2. customto remove the organic solvent
  3. filtrationThe suspension was collected by filtration
  4. washwashed with water (50 mL) and air
  5. customdried

Sources & evidence

ORD record
ord-d96db8fc0c8246079f16bd0a86311a71
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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