Acetic Acid → 5-(4-benzyl-1-piperazinyl)-1H-indazole

HRID 1269738Notes

Reaction equation

C(O)(=O)C.O.[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24](C2CCCCO2)[N:23]=[CH:22]3)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[CH:22]3)[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Acetic acid (2.6 ml) and water (0.7 ml) were added to a solution of 5-(4-benzyl-1-piperazinyl)-1-tetrahydro-2H-pyran-2-yl-1H-indazole (100 mg, 0.266 mmol) in tetrahydrofuran (1.3 ml) at room temperature and stirred 80° C. for 7 hours. Then, the reaction solution was concentrated and the resulting residue was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a thin-layer chromatography (eluent: chloroform/methanol=95/5) to obtain 5-(4-benzyl-1-piperazinyl)-1H-indazole (37 mg, 47%).

Workup

concentrationThen, the reaction solution was concentrated
additionthe resulting residue was diluted with ethyl acetate
washwashed with a saturated aqueous sodium hydrogencarbonate solution
dry with materialThe organic layer was dried over anhydrous sodium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customthe resulting residue was purified by a thin-layer chromatography (eluent: chloroform/methanol=95/5)

Sources & evidence

ORD record: ord-637009381bcf4269a8a1c5a5a670423a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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