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CAS No. : | 276248-50-1 | MDL No. : | MFCD09752680 |
Formula : | C7H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BCDBHIAXYFPJCT-LURJTMIESA-N |
M.W : | 143.18 | Pubchem ID : | 18727136 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With thionyl chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: 94 percent / HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: 94 percent / HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h 7: Et3N / CH2Cl2 / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: 94 percent / HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: 94 percent / HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: 94 percent / HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h 7: Et3N / CH2Cl2 / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h 7: Et3N / CH2Cl2 / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 97 percent / HOBt; EDC; Et3N / dimethylformamide / 40 h / 20 °C 2: 97 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C 3: HOBt; Et3N; EDC / dimethylformamide / 36 h / 20 °C 4: 4N HCl / dioxane / 2 h 5: HOBt; NMM; EDC / dimethylformamide / 36 h / 20 °C 6: 4N HCl / dioxane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 80℃; for 0.5h; | 118.3 To a solution of 1-(2-chloroacetyl)-5-[(4-phenyl-5-trifluoromethyl-2-thienyl)methoxy]indoline (360 mg) in acetonitrile (3.0 mL), DIEA (347 µL) and (3S)-piperidinecarboxylic acid methyl ester (143 mg) were added at room temperature, and the mixture was stirred for 30 minutes at 80°C. The reaction mixture was concentrated under reduce pressure, and to the resultant residue, water (5.0 mL), saturated aqueous sodium hydrogencarbonate solution (3.0 mL), and a 10% methanol/chloroform mixture (10 mL) were added for phase separation. The aqueous layer was extracted with a 10% methanol/chloroform mixture (3 × 5.0 mL), and the extracts were combined and dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (Biotage 25M), whereby the title compound (322 mg) was yielded. 1H-NMR (CDCl3) δ: 1.47-1.69(2H,m),1.70-1.78(1H,m),1.89-1.97(1H,br m),2.25(1H,td,J=9.8,2.4Hz),2.44(1H,t,J=9.8Hz),2.65(1H,ddd,J=9 .8,13.7,3.9Hz),2.79-2.86(1H,m),3.03-3.08 (1H,m), 3.17 (2H, t, J=8.3Hz), 3.25 (2H, s), 3.64 (3H, s), 4.18 (2H, d t,J=3.9,8.3Hz),5.20(2H,s),6.82(1H,d,J=8.8Hz),6.85(1H,br s),7.06(1H,s),7.43-7.39(5H,m),8.18(1H,d,J=8.8Hz). MS(ESI)m/z:559(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-(tert-butoxycarbonyl)piperidine-(3S)-carboxylic acid methyl ester With hydrogenchloride In 1,4-dioxane at 20℃; for 16h; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water | 118.2 To 1-(tert-butoxycarbonyl)piperidine-(3S)-carboxylic acid methyl ester (2.88 g), 4N HCl/1,4-dioxane (5.0 mL) was added at room temperature, and the mixture was stirred for 16 hours. The resultant mixture was concentrated under reduced pressure. To the residue, water (15.0 mL) was added, and the pH of the resultant mixture was adjusted to 9 with saturated aqueous sodium hydrogencarbonate solution. The resultant mixture was extracted with a 10% methanol/chloroform mixture (3 × 15.0 mL), and the extracts were combined and dried over sodium sulfate anhydrate, and further dried under reduced pressure, whereby the title compound (577 mg) was yielded. 1H-NMR (CDCl3) δ: 1.40-1.52(1H,m),1.63-1.72(2H,m),1.95-2.02(1H,m),2.46(1H,tt,J=9.8,3.9Hz),2.64(1H,ddd,J=9.8,12.4,3.2 Hz),2.82(1H,dd,J=12.4,9.3Hz),2.93(1H,dt,J=12.4,3.9Hz),3.16(1H ,dd,J=12.4,3.2Hz),3.68(3H,s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide | ||
In N,N-dimethyl-formamide at 60℃; for 4h; basic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid at 25℃; for 16h; | C.6 Production of (S)-nipecotic acid Comparative Example 6 Production of (S)-nipecotic acid Methanesulfonic acid (576 mg, 6 mmol) was added to a solution of (S)-N-(tert-butoxycarbonyl)nipecotic acid (1145 mg, 5 mmol) and methanol (5 mL). When the mixture was stirred at 25° C. for 16 hours, (S)-methyl nipecotate was produced, and the object (S)-nipecotic acid was not produced. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 150℃; for 0.5h; Microwave irradiation; | Intermediate 9 (R) -methyl 1- (8-amino-1-bromoimidazo [1, 5-a] pyrazin-3-yl) piperidine-3-carboxylate[0600]To a solution of (S) -methyl piperidine-3-carboxylate (500mg, 3.5 mmol) and 1, 3-dibromoimidazo [1, 5-a] pyrazin-8-amine (673 mg, 2.3 mmol) in NMP (2.5 mL) was added DIEA (2.25g, 17.5mmol) . The mixture was stirred at150 under microwave for 0.5 hour. After cooling to room temperature, the mixture was added H2O (10mL) , extracted by EA (10mL) . The organic layer was dried over anyhydrous Na2SO4, concentrated, purified by pre-HPLC to give (S) -methyl 1- (8-amino-1-bromoimidazo [1, 5-a] pyrazin-3-yl) piperidine-3-carboxylate. 1H NMR (400MHz, DMSO-d6) : 7.44 (d, J5.0 Hz, 1H) , 6.91 (d, J5.0 Hz, 1H) , 3.29 (d, J12.5 Hz, 2H), 3.23 -3.13 (m, 2H) , 3.02 -2.93 (m, 1H) , 2.72 (br. s. , 1H) , 1.95 -1.87 (m, 1H) , 1.76 -1.64 (m, 3H) ppm. MS (ESI) : M/Z (M+1) 524.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In dichloromethane at 20℃; for 5h; | 4.2.1 Procedure a of Scheme 1 General procedure: A mixture of methyl piperidine-4-carboxylate (2g, 14mmol) (20a), 2-chloroacetyl chloride (1.16mL, 15.4mmol) and K2CO3 (5.8g, 42mmol) in DCM was stirred for 5hat rt. Upon completion, the solvent was removed in vacuo. Water was added and the mixture was extracted with ethyl acetate (20mL×3). The organic layer was washed with water, 1N HCl and brine, dried over Na2SO4, and evaporated. The compound 21a (methyl piperidine-4-carboxylate) was obtained as a yellow oil (2.072g, 67.4% yield). This oil was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 5 h / 20 °C 2: potassium carbonate; potassium iodide / acetone / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane / 5 h / 20 °C 2: potassium carbonate; potassium iodide / acetone / 5 h / Reflux 3: sodium hydroxide / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2: lithium hydroxide monohydrate; water / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2.1: lithium hydroxide monohydrate; water / 2 h / 20 °C 3.1: thionyl chloride / dichloromethane / 2 h / 20 °C 3.2: 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | E.78.1 Step1 To a solution of R-1 (220 mg, 1.0 mmol) in DMF (4 mL) is added R-8 (210 mg, 1.2 mmol) and K2CO3 (691 mg, 5.0 mmol), then stirred at 80 oC for 2 h. The mixture is treated with H2O (50 mL) and extracted with EtOAc (50 mL x 3). The combined organic layers are washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated. The residue is purified by flash chromatography (EtOAc:Petroleum ether = 1:1) to afford I-3 (310 mg, 95%) [Analytical Method I, ret time = 2.16 min, m/z = 330.1]. |
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