Lithium Hydroxide → 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid

HRID 8255Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Li+]>CO>[CH3:27][C:23]1[N:22]=[C:21]([C:20]2[C:16]([C:10]3[C:9]4[C:14](=[CH:15][C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=4)[N:13]=[CH:12][CH:11]=3)=[C:17]3[CH2:30][CH2:29][CH2:28][N:18]3[N:19]=2)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid ethyl ester (250 mg, 0.6 mmol) in methanol (4 mL) at room temperature is added 1 N lithium hydroxide (1.2 mL, 1.2 mmol). The mixture is heated at 60° C. for 4 h. The mixture is cooled to room temperature and concentrated in vacuo. The mixture is diluted with water and acidified to pH 6 with 1 N hydrochloric acid. The aqueous solution is extracted with dichloromethane 5 times. The combined organic extracts are dried (sodium sulfate), filtered, and concentrated in vacuo to yield the title compound, 150 mg (65%), as an off white solid.

Workup

temperatureThe mixture is cooled to room temperature
concentrationconcentrated in vacuo
additionThe mixture is diluted with water
extractionThe aqueous solution is extracted with dichloromethane 5 times
dry with materialThe combined organic extracts are dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2b84cbe4087445e9a83ca73bab924620
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Reaction notes

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