Hydrochloric Acid → 1-[5-(Morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 38799Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of methyl 1-[5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg) and methanol (2 mL) was added a 1 M aqueous sodium hydroxide solution (670 μL) at room temperature, followed by stirring at 60° C. for 3 hours. To the reaction mixture were added 1 M hydrochloric acid and water, followed by stirring at room temperature for 30 minutes, and then the resulting precipitate was filtered and washed with water to obtain 1-[5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (95 mg) as a white powder.

Workup

stirringby stirring at room temperature for 30 minutes
filtrationthe resulting precipitate was filtered
washwashed with water

Sources & evidence

ORD record: ord-3cfbd239521f49f79a647e501c936a5e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524727B2

Reaction notes

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