Ethanol → HCID 136336861, compound

HRID 69133Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C:30]([O:32]CC)=[O:31])[CH2:25]2)=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.C(O)C.[OH-].[Na+].O>C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C:30]([OH:32])=[O:31])[CH2:25]2)=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 95 mg of ethyl (3R)-1-{[7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinolin-8-yl]carbonyl}piperidine-3-carboxylate were added 5 mL of ethanol and 200 μL of a 3 M aqueous sodium hydroxide solution, followed by stirring at 70° C. for 9 hours. The reaction mixture was cooled, and water and ethyl acetate were added thereto, and then the organic layer was separated. The aqueous layer was adjusted to about pH 4 with 1 mL of 1 M hydrochloric acid, then the solution was coevaporated with toluene. After forming a precipitate, f the precipitared powder was collected by filtration. The obtained powder was dried under reduced pressure to obtain 71 mg of (3R)-1-{[7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinolin-8-yl]carbonyl}piperidine-3-carboxylic acid as white powder.

Workup

temperatureThe reaction mixture was cooled
customthe organic layer was separated
customAfter forming a precipitate, f the precipitared powder
filtrationwas collected by filtration
customThe obtained powder was dried under reduced pressure

Sources & evidence

ORD record: ord-ad2258c94b814fc0bbd3fc8416da3f88
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822448B2

Reaction notes

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