Lithium Hydroxide → HCID 71075024, compound

HRID 1028112Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([C:16]3[S:20][C:19]([N:21]4[CH2:26][CH2:25][CH:24]([C:27]([O:29]CC)=[O:28])[CH2:23][CH2:22]4)=[N:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[N:4]=1.[OH-].[Li+]>O1CCCC1.CO.CC1CCCO1>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([C:16]3[S:20][C:19]([N:21]4[CH2:26][CH2:25][CH:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]4)=[N:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[N:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate (22 mg, 0.046 mmol) in tetrahydrofuran (0.5 mL) and methanol (0.5 mL) was added 1M aqueous lithium hydroxide (0.5 mL, 0.5 mmol) and the mixture was heated to 90° C. for 90 minutes. The mixture was cooled to room temperature, diluted with 2-methyltetrahydrofuran (30 mL), and, washed with 1 N aqueous hydrochloric acid (30 mL) and brine (30 mL). The aqueous layers were further extracted with 2-methyltetrahydrofuran (30 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to provide 1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylic acid as a white solid. MS APCI: [M+H]+ m/z 450.1.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with 1 N aqueous hydrochloric acid (30 mL) and brine (30 mL)
extractionThe aqueous layers were further extracted with 2-methyltetrahydrofuran (30 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5a246fe4755c410eb9bc3c8c6d909144
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735417B2

Reaction notes

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