Sodium Hydroxide → HCID 15522352, compound

HRID 965352Notes

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 x 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 x 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-57740d52cc044ad59f59a0e2b6593f79
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773530

Reaction notes

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