Water → HCID 117864549, compound

HRID 1486355Notes

Reaction equation

C(OC(=O)[NH:7][C:8]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:32])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][C:19]([CH3:31])=[CH:18][C:17]=12)=[O:12])(C)(C)C.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[NH2:7][C:8]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:32])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][C:19]([CH3:31])=[CH:18][C:17]=12)=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

20 mg (0.039 mmol) of rac-{1-[({7-[(3-fluoropyridin-2-yl)methoxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 144A) were dissolved in 1 ml of trifluoroacetic acid. The reaction mixture was heated to 50° C. for 1 hour. Water was added, and the pH was adjusted to −9 with 2 N sodium hydroxide solution. The aqueous phase was extracted with dichloromethane, separated off and concentrated under reduced pressure. The residue was purified by preparative HPLC chromatography (Method 21), which gave 1.59 mg (10% yield) of the target compound.

Workup

extractionThe aqueous phase was extracted with dichloromethane
customseparated off
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC chromatography (Method 21), which

Sources & evidence

ORD record: ord-7256099ea0c543a9a62d014201b7d3f1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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