Hydrochloric Acid → 3-Cyclopropyl-3-(6-(((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)(methyl)amino)pyrimidin-4-yl)propanoic acid

HRID 709620Notes

Reaction equation

[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([N:17]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=4[F:34])=[C:22]([O:35][CH2:36][CH:37]([CH3:39])[CH3:38])[N:21]=3)[CH3:18])[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([N:17]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=4[F:34])=[C:22]([O:35][CH2:36][CH:37]([CH3:39])[CH3:38])[N:21]=3)[CH3:18])[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(6-(((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)(methyl)amino)pyrimidin-4-yl)propanoate (30 mg) in methanol (3.0 mL) was added 1N aqueous sodium hydroxide solution (0.17 mL), and the mixture was stirred at 50° C. for 3 hr. 1N Hydrochloric acid was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from hexane/diethyl ether to give the title compound (20 mg) as a white solid.

Workup

extractionthe reaction mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was recrystallized from hexane/diethyl ether

Sources & evidence

ORD record: ord-516880713e424f9a9879e41936deffd8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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