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CAS No. : | 116258-17-4 | MDL No. : | MFCD08669797 |
Formula : | C12H18Br2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SOMPEQIPSQFVMO-AQEKLAMFSA-N |
M.W : | 350.09 | Pubchem ID : | 14612542 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 84.82 |
TPSA : | 15.27 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.31 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 2.54 |
Log Po/w (SILICOS-IT) : | 1.83 |
Consensus Log Po/w : | 1.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.24 |
Solubility : | 0.0201 mg/ml ; 0.0000574 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.173 mg/ml ; 0.000494 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.11 |
Solubility : | 0.271 mg/ml ; 0.000774 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.98 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
89% | With hydrogen bromide In acetic acid at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogen at 40℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 15.A tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Example 15A tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1R,4R)-2-(benzyl)-2,5-diazabicylo[2.2.1]heptane dihydrobromide (12.4 g, 35.5 mmol), prepared as described in (J. Med. Chem., (1990) 33, 1344) and K2CO3 (16.2 g, 117 mmol) in 100 mL of DMF were treated with di-tert-butyl dicarbonate (8.1 g, 37 mmol) at ambient temperature. After stirring for 16 hours, the mixture was filtered and the filtrate diluted with water (500 mL). The mixture was extracted with Et2O (3x300 mL). The extracts were combined, washed with 50% brine (10x20 mL), dried over MgSO4, and the solvent removed under reduced pressure to provide the title compound (9.7 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 1.62 (m, 1H), 1.79 (d, J=9.2 Hz, 1H), 2.51 (m, 1H), 2.75 (m, 1H) 3.07 (t, J=10.2 Hz, 1H), 3.32-3.41 (m, 2H), 3.67 (s, 1H), 4.16 (d, 9.8 Hz, 1H), 7.19-7.33 (m, 5H); MS (DCI/NH3) m/z 199 (M+H)+, 216 (M+NH4)+. |
94% | With potassium carbonate In DMF (N,N-dimethyl-formamide) for 16h; | 15A EXAMPLE 15; (1R,4R)-2-(6-chloro-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane 4-methylbenzenesulfonate; Example 15A; tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1R,4R)-2-(benzyl)-2,5-diazabicylo[2.2.1]heptane dihydrobromide (12.4 g, 35.5 mmol), prepared as described in (J. Med. Chem., (1990) 33, 1344) and K2CO3 (16.2 g, 117 mmol) in 100 mL of DMF were treated with di-tert-butyl dicarbonate (8.1 g, 37 mmol) at ambient temperature. After stirring for 16 hours, the mixture was filtered and the filtrate diluted with water (500 mL). The mixture was extracted with Et2O (3×300 mL). The extracts were combined, washed with 50% brine (10×20 mL), dried over MgSO4, and the solvent removed under reduced pressure to provide the title compound (9.7 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 1.62 (m, 1H), 1.79 (d, J=9.2 Hz, 1H), 2.51 (m, 1H), 2.75 (m, 1H) 3.07 (t, J=10.2 Hz, 1H), 3.32-3.41 (m, 2H), 3.67 (s, 1H), 4.16 (d, 9.8 Hz, 1H), 7.19-7.33 (m, 5H); MS (DCI/NH3) m/z 199 (M+H)+, 216 (M+NH4)+. |
94% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 25.A tert-butyl(1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Example 25A tert-butyl(1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1R,4R)-2-(benzyl)-2,5-diazabicylo[2.2.1]heptane dihydrobromide (12.4 g, 35.5 mmol), prepared as described in (J. Med. Chem., (1990) 33, 1344) and K2CO3 (16.2 g, 117 mmol) in 100 mL of DMF were treated with di-tert-butyl dicarbonate (8.1 g, 37 mmol) at ambient temperature. After stirring for 16 hours, the mixture was filtered and the filtrate diluted with water (500 mL). The mixture was extracted with Et2O (3*300 mL). The extracts were combined, washed with 50% brine (10*20 mL), dried over MgSO4, and the solvent removed under reduced pressure to provide the title compound (9.7 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 1.62 (m, 1H), 1.79 (d, J=9.2 Hz, 1H), 2.51 (m, 1H), 2.75 (m, 1H) 3.07 (t, J=10.2 Hz, 1H), 3.32-3.41 (m, 2H), 3.67 (s, 1H), 4.16 (d, 9.8 Hz, 1H), 7.19-7.33 ppm (m, 5H); MS (DCl/NH3) m/z 199 (M+H)+, 216 (M+NH4)+. |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C 4: p-toluenesulfonic acid / ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C 4: ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: aq. H2O2; NaOH / ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: aq. H2O2; NaOH / ethanol / 20 °C 5: CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: triethylamine / toluene / 28 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: triethylamine / toluene / 28 h / 100 °C 4: ethyl acetate / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: Amberlyst resin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 - 85 °C 4: TFA / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: TFA / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: triethylamine / CH2Cl2 / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: triethylamine / CH2Cl2 / 3 h / 20 °C 4: 60 percent / ethyl acetate / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: 59 percent / 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroisoquinoline / toluene / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: 59 percent / 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroisoquinoline / toluene / 16 h / 20 °C 4: ethyl acetate / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: ethyl acetate; ethanol / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: (S)-(-)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: (S)-(-)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0); sodium tert-butoxide / toluene / 5 h / 80 °C 4: p-toluenesulfonic acid / ethyl acetate; ethanol / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: p-toluenesulfonic acid / ethyl acetate / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: p-toluenesulfonic acid / ethyl acetate; ethanol / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: p-toluenesulfonic acid / ethyl acetate / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: H2 / Pd/C / ethanol / 6 h / 40 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: 52 percent / sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / dimethylformamide / 16 h / 20 °C 2: H2 / Pd/C / ethanol / 16 h / 760.05 Torr 3: 52 percent / sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 4: 0.121 g / Amberlyst 15 / acetonitrile / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 74.2 percent / triethylamine, pyridine / 1 h / 0 °C 2: 74 percent / toluene / Heating 3: 91 percent / lithium borohydride / tetrahydrofuran / 0 - 25 °C 4: 86 percent / pyridine / 2 h / 10 °C 5: 90 percent / toluene / 9 h / Heating 6: 89 percent / HBr / acetic acid / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / lithium borohydride / tetrahydrofuran / 0 - 25 °C 2: 86 percent / pyridine / 2 h / 10 °C 3: 90 percent / toluene / 9 h / Heating 4: 89 percent / HBr / acetic acid / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 74 percent / toluene / Heating 2: 91 percent / lithium borohydride / tetrahydrofuran / 0 - 25 °C 3: 86 percent / pyridine / 2 h / 10 °C 4: 90 percent / toluene / 9 h / Heating 5: 89 percent / HBr / acetic acid / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 86 percent / pyridine / 2 h / 10 °C 2: 90 percent / toluene / 9 h / Heating 3: 89 percent / HBr / acetic acid / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / toluene / 9 h / Heating 2: 89 percent / HBr / acetic acid / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / H2 / 10percent Pd/C / 8 h / 40 °C 2: 47 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 91 percent / H2 / 10percent Pd/C / 8 h / 40 °C 2: 92 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / 70 - 75 °C 3: 1 N aq. NaOH / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / H2 / 10percent Pd/C / 8 h / 40 °C 2: 92 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / 70 - 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 120℃; for 18h; | 168 The monochlor compound of preparation 120 (180mg, 0. 52mmol), (1 R, 4R)-2- benzyl-2, 5-DIAZABICYCLO [2.2. 1] heptane dihydrobromide (EP 400661, ex 8) (545mg, 2. 90MMOL) and N-ethyldiisoproylamine (723µL, 4. 16MMOL) were dissolved in DIMETHYLSULFOXIDE (3mL) and the reaction mixture heated to 120°C for 18 hours in a sealed vessel. The reaction mixture was partitioned between water (50mL) and ethyl acetate (50ML) and the aqueous separated and washed with ethyl acetate (50mL). The organics were combined, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate: methanol (100: 0 to 95: 5) to yield the title product, 62mg. 'H NMR (CD30D, 400MHZ) 8 : 0.12 (t, 3H), 1.96 (m, 1H), 2.09 (m, 1H), 2.38 (s, 3H), 2.42 (s, 3H), 2.88 (m, 1 H), 3.08 (m, 1 H), 3.59 (m, 3H), 3.80-3. 95 (m, 7H), 4.62 (m, 2H), 6.92 (d, 1H), 7.35 (m, 5H), 8.12 (d, 1H), 8.35 (m, 1H). LRMS: m/z APCI+ 499 [MH] + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A 1R,4R-5-PHENYLMETHYL-2,5-DIAZABICYCLO-(2.2.1)HEPTANE, DIHYDROBROMIDE 1R,4R-5-PHENYLMETHYL-2,5-DIAZABICYCLO-(2.2.1)HEPTANE, DIHYDROBROMIDE To a hot solution of 17 mL hydrobromic acid 33% in acetic acid at 70° C. was added 1 g (2.9 mmoles) of 1R,4R-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo (2.2.1) heptane. The solution was stirred for 12 hours at 70° C. The suspension was cooled and concentrated to one third, cooled to 10° C. The precipitate was filtered, washed with acetic acid and acetone to afford 0.9 g of titled compound. MP 275° C.; [α]D =-0.38° (C=1, H2 O) | ||
1294 g (89%) | (1R,4R)-5-PHENYLMETHYL-2,5-DIAZABICYCLO-[2.2.1]-HEPTANE, DIHYDROBROMIDE (9) (1R,4R)-5-PHENYLMETHYL-2,5-DIAZABICYCLO-[2.2.1]-HEPTANE, DIHYDROBROMIDE (9) To a hot solution of 2.85 L of hydrobromic acid 33% in acetic acid* at 70° C. there was added 1428 g (4.17 moles) of (1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo-[2.2.1]-heptane (8). The solution was stirred for 12 h. The resulting suspension was cooled (18°-20° C.). The precipitate was filtered, washed with diisopropylether and dried at 40° C. under reduced pressure to give 1294 g (89%) of the titled compound. M.P. =276° C. [α]D =-0.38° (c=1, H2 O). |
Tags: 116258-17-4 synthesis path| 116258-17-4 SDS| 116258-17-4 COA| 116258-17-4 purity| 116258-17-4 application| 116258-17-4 NMR| 116258-17-4 COA| 116258-17-4 structure
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