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CAS No. : | 944238-89-5 | MDL No. : | MFCD09997870 |
Formula : | C11H20N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RBLOMFQUEUBEBG-IUCAKERBSA-N |
M.W : | 212.29 | Pubchem ID : | 45789463 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 1 h / 150 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 1 h / 150 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 3: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 16 h / 25 °C 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 150 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 3: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 16 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In acetonitrile at 150℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.3 g | With N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene for 0.166667h; | 5.6.154.A Part A. (1S.4Sl-2-tert-Butyl 5-isopropyl 2.5-diazabicyclo[2.2.1Jheptane-2.5-dicarboxylate To a stirred, ambient temperature, solution (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate [113451-59-5] (1.0 g, 5.0 mmol) and Hunig's base [7087-68-5] (1.4 ml, 8.0 mmol) inethyl acetate (120 ml) was slowly added a 1.0M solution of isopropyl chloroformate in toluene (5.120 ml) over the course of 10 minutes. The reaction was allowed to stir over night then was washed withbrine, dried (MgS04), and evaporated to obtain 1.3 g of yellow oil. LRMS (ESI) mjz 285.1 [(M+H)]+,calc'd for C14H24N204: 284.35. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / toluene; ethyl acetate / 0.17 h 2: hydrogenchloride / methanol / 2 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: chloroform / 1 h / Reflux 2: hydrogenchloride / methanol; chloroform |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 1h; Reflux; | 4.1.3. (S)-4,11-Dihydroxy-3-((pyrrolidin-3-ylamino)methyl)-1Hnaphtho[2,3-f]indole-5,10-dione dihydrochloride (6) General procedure: A stirring solution of iodomethylate 5 (100 mg, 0.2 mmol) and(S)-1-Boc-3-aminopyrrolidine (100 mg, 2.5 mmol) in chloroform (10 mL) was refluxed for 1 h. The mixture was diluted with chloroform (25 mL), washed with water and aqueous solution of NaHCO3 (1%), dried, and evaporated. The residue was purified by column chromatography on silica gel in chloroform-methanol(2:0→2:1). The red solid obtained after evaporation was dissolved in hot chloroform (1 mL), and a solution of HCl in methanol (1.25 N,1 mL) was added. The mixture was stirred overnight and evaporated.The residue was dissolved in hot water (0.5 mL), filtered and then product was precipitated with acetone-ether mixture (1:1),collected by filtration and dried. The yield of dihydrochloride 6 was 58 mg (61%) as a red solid, mp 212-213°C (dec.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.6 g | With tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene | 310.A Example 310. Synthesis of (1R,4R)-2-((6-methoxy-2,3-dihydro-1H-inden-1-yl)methyl)-5- phenyl-2,5-diazabicyclo[2.2.2]octane A. To a solution of (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate (500 mg, 2.36 mmol) in PhMe (30 mL) was added iodobenzene (1.44 g, 7.08 mmol),potassium 2- methylpropan-2-olate (0.79 g, 7.08 mmol) and Pd2(dba)3 (0.22 g, 0.24 mmol), BINAP (0.29 g, 0.47 mmol). The reaction were filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with EtOAc (30%) and hexanes (70%) to provide (1S,4S)-tert-butyl 5- phenyl-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (0.6 g, 2.08 mmol) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triethylamine In 1,4-dioxane at 50℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 1,4-dioxane / 3 h / 50 °C 2: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 4 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / 1,4-dioxane / 3 h / 50 °C 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 4 h / 100 °C 3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 3.2: 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 18h; | 43 tert- Butyl (lS,4S)-5-(2-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo- 6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-ethylphenoxy)ethyl)-2,5- diazabicyclo [2.2.2] octane-2-carboxylate. To a solution of ter/-butyl (lS,4S)-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (0.057 g, 0.27 mmol, 1.2 eq) in DMF (2.26 mL, 0.100 M) was added 5-[5-[4-(2-bromoethoxy)-3-ethyl-phenyl]-8-oxo-6-thioxo-5,7- diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile (0.125 g, 0.23 mmol, 1 eq), (prepared as described herein), and DIEA (0.14 mL, 0.79 mmol, 3.5 eq). The mixture was heated to 60 °C, while stirring for 18 h. After concentration under reduced pressure, the reaction mixture was purified by silica gel column chromatography (0-100% hexane/EtOAc) to give tert- butyl (lS,4S)-5-(2-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7- diazaspiro[3.4]octan-5-yl)-2-ethylphenoxy)ethyl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (0.130 g, 0.19 mmol, 84.0% yield) as a beige solid. MS (ESI) m/z 685.2 [M+l]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 mg | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 1h; | 1.8 Synthesis of tert-butyl (1S,4S)-5-{2-[4-(4-chlorophenyl)-5-(pyridin-4-yl)-1H-imidazol-1-yl]acetyl}- 2,5-diazabicyclo[2.2.2]octane-2-carboxylate / Intermediate 66 2-[4-(4-Chlorophenyl)-5-(4- pyridyl)imidazol-1-yl]acetic acid;2,2,2-trifluoroacetic acid (Intermediate 2a) (75 mg, 0.137 mmol) and tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (30 mg, 0.141 mmol) were dissolved in a solution of EtOAc (1.5 mL) and DIPEA (120 uL, 0.687 mmol), then T3P (50%, 165 uL, 0.277 mmol) was added. The reaction was stirred at RT for 1 h. The reaction mixture was diluted with EtOAc and partitioned with water. The organic phase was separated and the aqueous was extracted with DCM/MeOH (9:1). The combined organics were concentrated in vacuo. The crude product was purified via flash chromatography (10 g, silica) eluting with 0-10% 2M ammonia MeOH/DCM to afford the title compound (70 mg, 95% yield) as a yellow solid.1HNMR(400 MHz, DMSO-d6) δ 8.66 - 8.61 (m, 2H), 7.81 - 7.79 (m, 1H), 7.41 - 7.37 (m, 2H), 7.31 - 7.25 (m, 4H), 4.95 - 4.79 (m, 1H), 4.77 - 4.72 (m, 1H), 4.46 - 3.99 (m, 2H), 3.58 - 3.38 (m, 2H), 3.38 - 3.25 (m, 2H), 1.89 - 1.78 (m, 1H), 1.74 - 1.64 (m, 3H), 1.43 (s, 9H). LCMS (Analytical Method H) Rt = 0.55 min, MS (ESIpos): m/z 508.3, 510.3 [M+H]+, Purity = 95% |