Hydrochloric Acid → 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoic acid

HRID 595318Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[N:17][N:18]([CH:20]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[CH3:21])[CH:19]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:7]=1.O.[OH-].[Na+].Cl>C1COCC1.CO.C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[N:17][N:18]([CH:20]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)[CH3:21])[CH:19]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of methyl 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoate (125 mg, 0.302 mmol) in THF (5.0 mL), methanol (1.0 mL), and water (1.0 mL) was diluted with sodium hydroxide (1.0 M in water, 1.0 mL, 1.0 mmol). The reaction mixture was stirred and heated to 50° C. for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with hydrochloric acid (1.0 M in water, 1.0 mL, 1.0 mmol) while stirring. The resulting suspension was diluted with ethyl acetate (100 mL) and brine (10 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoic acid. The material was used without purification in the subsequent step. MS ESI calcd. for C23H22N5O2 [M+H]+ 400. found 400.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
stirringwhile stirring
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3cbcda516e0e45cab3b454ef5e383729
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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