Chlorosuccinimide → N-{2-[(8S)-1-chloro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide

HRID 887818Notes

Reaction equation

[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]3[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:8]=32)=[N:3]1.[Cl:20]N1C(=O)CCC1=O>C(#N)C>[Cl:20][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[C:8]1[C@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:13][C:7]=1[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-{2-[(8S)-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl]ethyl}acetamide (80 mg, 0.311 mmol) in acetonitrile (3.1 mL) was added N-chlorosuccinimide (45.7 mg, 0.342 mmol), and the mixture was stirred at 50° C. for 5 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90), preparative HPLC (acetonitrile/water=10/90→90/10) and recrystallization (ethyl acetate/hexane) to give the title compound (20.1 mg, yield 22%).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90), preparative HPLC (acetonitrile/water=10/90→90/10) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0afb3554768e4e1b85edf14c6445b701
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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