Hydrochloric Acid → 2-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid

HRID 1930101Notes

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]C)=[O:26])=[CH:20][C:19]=3[Cl:29])=[CH:14][CH:13]=2)[C:9]([CH3:30])=[N:8][C:7]=1[CH3:31])(=[O:5])[NH2:4].Cl>C(O)(C)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=3[Cl:29])=[CH:16][CH:17]=2)[C:9]([CH3:30])=[N:8][C:7]=1[CH3:31])(=[O:5])[NH2:4]

Participants

Conditions

Temperature: 45 °C

Procedure

Powdered potassium hydroxide (45.2 mg, 0.81 mmol) was added in one portion to methyl 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetate (Intermediate 1-1; 110 mg, 0.27 mmol) in tert-butanol (10 mL) at 45° C. The resulting solution was stirred at 45° C. for 15 minutes, a thick white suspension slowly formed. 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 (5 mL) and dried under vacuum to afford 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid (82 mg, 77%) as a white solid.

Workup

customa thick white suspension slowly formed
customthe mixture was evaporated
customto remove the organic solvent
filtrationThe suspension was collected by filtration
washwashed with water (5 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-8eb07a3892094ef2be74764670fd4c29
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188092B2

Reaction notes

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