Hydrochloric Acid → HCID 58168828, compound

HRID 38801Notes

Reaction equation

[C:1]12([NH:11][C:12]3[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22]([N:24]4[CH2:29][CH2:28][CH:27]([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]4)=[O:23])=[CH:14][N:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CO.[OH-].[Na+].Cl>O.O1CCCC1>[C:1]12([NH:11][C:12]3[N:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[C:15]([C:22]([N:24]4[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]4)=[O:23])=[CH:14][N:13]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of ethyl 1-{[2-(adamantan-1-ylamino)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidine-4-carboxylate (220 mg), methanol (3 mL) and tetrahydrofuran (3 mL) was added a 1 M aqueous sodium hydroxide solution (1.37 mL) at room temperature, followed by stirring at 60° C. for 2 hours. To the reaction mixture were added 1 M hydrochloric acid and water, followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, to the obtained residue was added water, followed by stirring for 30 minutes, and then the precipitate was collected by filtration and washed with water to obtain 1-{[2-(adamantan-1-ylamino)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidine-4-carboxylic acid (190 mg) as a white powder.

Workup

stirringby stirring at room temperature for 30 minutes
customThe solvent was evaporated under reduced pressure, to the obtained residue
additionwas added water
stirringby stirring for 30 minutes
filtrationthe precipitate was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-1f38d8d4273940f7823201a0bcc431bc
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524727B2

Reaction notes

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