N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide → N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)methanesulfonamide

HRID 1477865Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([N:25](COCC[Si](C)(C)C)[S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH:11]2[CH2:13][CH:12]2[C:14]#[N:15])[CH2:9][CH3:10])=[CH:4][CH:3]=1>Cl.CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH:11]2[CH2:13][CH:12]2[C:14]#[N:15])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide (14 mg) in 2 N HCl/EtOH (1 mL/1 mL) was stirred at 50° C. for 3 h, cooled to room temperature, concentrated, and extracted with ethyl acetate (10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified using a silica gel column (PE/EA=3/1) to afford the title compound as a brown solid. LC/MS m/z=429.1 [M+H]+.

Workup

temperaturecooled to room temperature
concentrationconcentrated
extractionextracted with ethyl acetate (10 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-995fcf1c575142c48980d4d0ebfd214a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403807B2

Reaction notes

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