Sodium Hydroxide → HCID 15522352, compound

HRID 276942Notes

Reaction equation

C([O:3][C:4]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]2[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:22][N:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=23)=[N:14]1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[C:4]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]2[C:21]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[N:22][N:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=23)=[N:14]1)([OH:5])=[O:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of cis-3-[2-(2-ethoxycarbonylmethyl-cyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (89.7 mg), 1N aqueous sodium hydroxide (1 ml), and dioxane (4 ml) was stirred at room temperature for 5 hours and at 70° C. for 4 hours. Dioxane was removed in vacuo. The remaining aqueous solution was diluted with water and extracted with ethyl acetate (10 ml). The aqueous layer was acidified with 1N hydrochloric acid and extracted with dichloromethane (10 ml×2). The combined extracts were washed with brine (10 ml), dried over anhydrous magnesium sulfate, and evaporated in vacuo to give colorless crystals of cis-3-[2-(2-carboxymethylcyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (71.4 mg).

Workup

customDioxane was removed in vacuo
additionThe remaining aqueous solution was diluted with water
extractionextracted with ethyl acetate (10 ml)
extractionextracted with dichloromethane (10 ml×2)
washThe combined extracts were washed with brine (10 ml)
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-8dae1002314e4ebaabad0a3b7dcdc9a5
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355640B1

Reaction notes

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