Structure of 919799-80-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 919799-80-7 |
Formula : | C10H19NO |
M.W : | 169.26 |
SMILES Code : | N[C@H]1CC[C@H](OCC2CC2)CC1 |
MDL No. : | MFCD24644648 |
InChI Key : | VQVVFYUZDFOHRA-UHFFFAOYSA-N |
Pubchem ID : | 62807939 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With hydrazine hydrate monohydrate; In ethanol; at 70℃; for 1h; | 12D: (iratti')-4-(Cyclopropylmethoxy)cyclohexanamine[00153] A stirred solution of 12C (620 mg, 2.071 mmol) in EtOH (10 mL) was treated with hydrazine monohydrate (0.152 mL, 3.11 mmol) and stirred at 70 C for 1 h. The reaction was judged complete by LCMS. Upon cooling, Et20 was added, and reaction was stirred at room temperature for lh. The resulting white solid was removed by filtration, and the filtrate was concentrated. The residue was triturated with Et20, the small amount of white solid was filtered, and the filtrate was concentrated to provide 12D (120 mg, 34 % yield) as pale brown oil. ]H NMR (400 MHz, CDC13) δ ppm 3.11(d, 2H, J = 6.8 Hz); 2.99-3.08(m, 1H); 2.48- 2.57 (m, 1H); 1.64-1.89(m, 6H); 1.06-1.18(m, 2H); 0.81-1.02 (m, 3H); 0.31-0.39(m, 2H); -0.02- 0.04(m, 2H). |
With hydrazine hydrate monohydrate; In ethanol; at 70℃; for 3h; | 2-((1R,4R)-4-(cyclopropylmethoxy)cyclohexyl)isoindoline-1,3-dione (L043-1, 1.27 g, 4.2 mmol) was dissolved in ethanol ( 10 mL), hydrazine hydrate (85%, 3 mL) was added.The reaction was stirred at 70C for 3h. After cooling to room temperature, filtration, the filtrate was concentrated,Diethyl ether (50 mL) was added and stirred for 5 min, then filtered, and the filtrate was concentrated to obtain compound L043-2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1h; | Compound L059-1 (600 mg, 1.7 mmol) and DIEA (438 mg, 3.4 mmol) were combinedIt was added to DCM (10 mL), compound L043-2 (431 mg, 2.6 mmol) was added in portions at 0C, and the reaction was carried out at room temperature for 1 hour.Work-up: DCM (20 mL) and water (30 mL) were added, the organic phase was extracted,The aqueous phase was extracted with 30 mL of DCM, and the combined organic phases were washed once with saturated brine.After drying over anhydrous sodium sulfate, it was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (PE:EA=5:1-1:1) to obtain compound L059-2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound L092-2 (400 mg, 1.38 mmol) was added to dichloromethane (6.0 mL),Then m-chloroperoxybenzoic acid (427 mg, 2.48 mmol, 70%) was added in portions,The reaction was carried out at room temperature for 0.5 hours. A solution of compound L043-2 (466 mg, 2.75 mmol) in DMF (1.0 mL) was added dropwise, and the reaction was carried out at room temperature for 0.5 h. To the reaction solution was added saturated sodium bicarbonate (10 mL), and the aqueous phase was extracted with ethyl acetate (10 mL×3 ), combine the organic phases,Washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (PE/EA=1/20-1/5) to obtain compound L115-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound L002-4 (270 mg, 0.64 mmol) and m-chloroperoxybenzoic acid (193 mg, 1.12 mmol) were dissolved in dichloromethane (4 mL). The mixture was stirred for 0.5 h at room temperature,Compound L043-2 (320 mg, 1.92 mmol) and DMSO (2 mL) were added to the reaction solution.The reaction solution was stirred at room temperature for 1 hour. The reaction solution was diluted with water (10 mL), extracted with ethyl acetate (10 mL*3), the organic phases were combined, washed with saturated brine (10 mL*2),Then add anhydrous sodium sulfate to dry. filter,The filtrate was concentrated and separated by column chromatography (petroleum ether/ethyl acetate=5/1) to obtain compound L112-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 2h; | 5-Chloro-8-iodo-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine (L017-1, 500 mg, 1.353 mmol) was dissolved in tetrahydrofuran (10 mL),Add <strong>[919799-80-7](1R,4R)-4-(cyclopropylmethoxy)cyclohexane-1-amine</strong> (L043-2, 274.80 mg, 1.623 mmol) and N,N-diisopropylethylamine ( 349.72 mg, 2.706 mmol). The reaction solution was stirred at room temperature for 2 h, then concentrated,The obtained crude product was separated by column chromatography (PE/EA=5/2) to obtain compound L043-3. |
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