Lithium Hydroxide → [4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-acetic acid

HRID 8243Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-acetic 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 residue is taken up in 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. MS ES− m/e 385 (M−1).

Workup

temperatureThe mixture is cooled to room temperature
concentrationconcentrated in vacuo
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-7dc08d5b00874fdcadab0f0a65ef94c2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Reaction notes

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