Sodium Hydroxide → HCID 66878341, compound

HRID 1466663Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([C:25]([CH3:32])([CH3:31])[C:26]([O:28]CC)=[O:27])[N:9]=2)[CH:7]=1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([C:25]([CH3:31])([CH3:32])[C:26]([OH:28])=[O:27])[N:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide2×

HCID 66899240HCID 66899240, compound

Product 1

HCID 66878341HCID 66878341, compound

Procedure

To a solution of ethyl 2-(3-(5-chloro-2-methoxyphenyl)-4-(pyrazolo[1,5-a]pyrimidine-3-carboxamido)-1H-pyrazol-1-yl)-2-methylpropanoate (0.918 g, 1.90 mmol, 1 equiv) was added 2 N aqueous sodium hydroxide solution (4 mL). After 18 h, additional 2 N aqueous sodium hydroxide solution (4 mL) was added. After 5 h, the reaction mixture was concentrated in vacuo, and the resulting residue was dissolved in water (15 mL). The aqueous solution was acidified with 6 N aqueous hydrochloric acid until pH=2. The resulting aqueous solution was extracted with ethyl acetate (3×30 mL). The combined organic was dried over anhydrous sodium sulfate, filtered, and concentrated to provide crude acid (quantitative). LCMS (ESI): M+H=455.1.

Workup

waitAfter 5 h
concentrationthe reaction mixture was concentrated in vacuo
dissolutionthe resulting residue was dissolved in water (15 mL)
extractionThe resulting aqueous solution was extracted with ethyl acetate (3×30 mL)
dry with materialThe combined organic was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customto provide crude acid (quantitative)

Sources & evidence

ORD record: ord-5251f39cb9be408ca4c85ea61d37d7c1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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