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Product Details of [ 876866-50-1 ]

CAS No. :876866-50-1 MDL No. :MFCD07838528
Formula : C10H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :CGVFHSAITNHPHR-UHFFFAOYSA-N
M.W : 197.23 Pubchem ID :8902915
Synonyms :

Safety of [ 876866-50-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 876866-50-1 ]

* 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.

  • Downstream synthetic route of [ 876866-50-1 ]

[ 876866-50-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 876866-50-1 ]
  • 1-(4-(4-aminopiperidin-1-yl)-3-(trifluoromethyl)phenyl)-3-(3-(6,7-dimethoxyquinolin-4-yloxy)phenyl)urea hydrochloride [ No CAS ]
  • 1-(cyclopropanecarbonyl)-N-(1-(4-(3-(3-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)ureido)-2-(trifluoromethyl)phenyl)piperidin-4-yl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;
  • 2
  • [ 876866-50-1 ]
  • (3S)-tert-butyl 3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate [ No CAS ]
  • C25H32F4N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(cyclopropylcarbonyl)piperidine-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Stage #2: (3S)-tert-butyl 3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate With 4-methyl-morpholine In dichloromethane at 25℃; for 60h; (3S)-tert-butyl 3-(1-(2-((2-(tert-butyl)phenyl)amino)-2-oxoacetyl)piperidine- 4-carboxamido)-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate (16) General procedure: To a solution of1-(2-((2-(tert-butyl)phenyl)amino)-2-oxoacetyl)piperidine-4-carboxylic acid(900.00 mg, 2.71 mmol, 1.05eq) and HOBt (488.23 mg, 3.61 mmol, 1.40eq) in DCM (100.00 mL) was added EDCI (692.68 mg, 3.61 mmol, 1.40eq) . The reaction mixture was stirred for 15 min, at which time a solution of(3S)-tert-butyl 3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy) pentanoate(911.00 mg, 2.58 mmol, 1.00eq) and NMM (783.19 mg, 7.74 mmol, 851.29 uL, 3.00eq) in DCM (100.00 mL) was added and then the mixture was stirred for an additional 60 h at 25 °C . The solution was diluted with DCM (100 mL) and washed with saturated aqueous sodium hydrogen carbonate (2 * 50 mL), saturated aqueous sodium chloride (1*100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography (ISCO; 12 g SepaFlash Silica Flash Column, Eluent of 0~30%EtOAc/Petroleum ether gradient 36 mL/min) to give(3S)-tert-butyl 3-(1-(2-((2-(tert-butyl)phenyl)amino)-2-oxoacetyl)piperidine- 4-carboxamido)-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate(16)(1.24 g, 1.71 mmol, 66% yield) as a yellow oil.
  • 3
  • [ 876866-50-1 ]
  • 6-(cyclopropylmethoxy)-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine [ No CAS ]
  • 1-(cyclopropanecarbonyl)-N-(6-(cyclopropylmethoxy)benzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethyl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 70℃; for 16h; 239.2 Step 2: Preparation of 1-(cyclopropanecarbonyl)-N-(6-(cyclopropylmethoxy)benzo[d]thiazol-2-yl)-N- (pyridin-3-ylmethyl)piperidine-4-carboxamide To a solution of 6-(cyclopropylmethoxy)-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine (127 mg, 0.41 mmol) in tetrahydrofuran (5 mL) were added 1-(cyclopropanecarbonyl)piperidine-4-carboxylic acid (80.0 mg, 0.41 mmol) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N- methylmethanaminium hexafluorophosphate N-oxide (233 mg, 0.61 mmol) and N,N- diisopropylethylamine (105 mg, 0.82 mmol). The reaction was stirred at 70 °C for 16 hours. The product was indicated via UPLC analysis. The reaction was filtered over Celite and the solvent was removed under the reduced pressure. Crude product was purified by prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston C1821*250mm 10µm column. The mobile phase was acetonitrile/0.01% aqueous formic acid) to give the product 1-cyclopropanecarbonyl-N- [6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(pyridin-3-yl)methyl]piperidine-4-carboxamide (28.6 mg, 0.068 mmol, 14 %) as a white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 8.58 (d, J = 1.2 Hz, 1H), 8.49 (dd, J = 4.0 Hz, 1H), 7.61-7.65 (m, 2H), 7.54 (d, J = 2.0Hz, 1H), 7.36-7.38 (m, 1H), 7.00-7.02 (m, 1H), 5.68 (s, 2H), 4.25-4.36 (m, 2H), 3.85-3.86 (m, 2H), 3.10-3.26 (m, 2H), 2.61-2.64 (m, 1H), 1.94-1.99 (m, 1H), 1.45-1.76 (m, 4H), 1.21-1.27 (m, 1H), 0.70-0.71 (m, 4H), 0.56-0.59 (m, 2H), 0.31-0.34 (m, 2H); LCMS (ESI) m/z: 491.3 [M+H]+.
14% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 70℃; for 16h; 239.2 Step 2: Preparation of 1-(cyclopropanecarbonyl)-N-(6-(cyclopropylmethoxy)benzo[d]thiazol-2-yl)-N- (pyridin-3-ylmethyl)piperidine-4-carboxamide To a solution of 6-(cyclopropylmethoxy)-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine (127 mg, 0.41 mmol) in tetrahydrofuran (5 mL) were added 1-(cyclopropanecarbonyl)piperidine-4-carboxylic acid (80.0 mg, 0.41 mmol) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N- methylmethanaminium hexafluorophosphate N-oxide (233 mg, 0.61 mmol) and N,N- diisopropylethylamine (105 mg, 0.82 mmol). The reaction was stirred at 70 °C for 16 hours. The product was indicated via UPLC analysis. The reaction was filtered over Celite and the solvent was removed under the reduced pressure. Crude product was purified by prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston C1821*250mm 10µm column. The mobile phase was acetonitrile/0.01% aqueous formic acid) to give the product 1-cyclopropanecarbonyl-N- [6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(pyridin-3-yl)methyl]piperidine-4-carboxamide (28.6 mg, 0.068 mmol, 14 %) as a white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 8.58 (d, J = 1.2 Hz, 1H), 8.49 (dd, J = 4.0 Hz, 1H), 7.61-7.65 (m, 2H), 7.54 (d, J = 2.0Hz, 1H), 7.36-7.38 (m, 1H), 7.00-7.02 (m, 1H), 5.68 (s, 2H), 4.25-4.36 (m, 2H), 3.85-3.86 (m, 2H), 3.10-3.26 (m, 2H), 2.61-2.64 (m, 1H), 1.94-1.99 (m, 1H), 1.45-1.76 (m, 4H), 1.21-1.27 (m, 1H), 0.70-0.71 (m, 4H), 0.56-0.59 (m, 2H), 0.31-0.34 (m, 2H); LCMS (ESI) m/z: 491.3 [M+H]+.
  • 4
  • [ 876866-50-1 ]
  • 6-(cyclopropylmethoxy)-N-(pyrimidin-5-ylmethyl)benzo[d]thiazol-2-amine [ No CAS ]
  • 1-cyclopropanecarbonyl-N-[6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(pyrimidin-5-yl)methyl]piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 70℃; for 16h; 242.2 Step 2: Preparation of N-(5-fluoro-1,3-benzothiazol-2-yl)-3-phenoxy-N-[(pyrimidin-5- yl)methyl]propanamide In a reaction vial, 5-fluoro-N-[(pyrimidin-5-yl)methyl]-1,3-benzothiazol-2-amine (95.9 mg, 0.37 mmol), 3-phenoxypropanoic acid (122 mg, 0.74 mmol), and triethylamine (0.26 mL, 1.8 mmol) were dissolved in dichloromethane (2 mL) with stirring. The reaction was cooled to 0 °C, and 50% propylphosphonic anhydride in ethyl acetate (0.70 mL, 0.92 mmol) was added. The reaction was warmed to room temperature and stirred for 2.5 days. The reaction was diluted with 10 mL deionized water and washed with 2x 10 mL portions of dichloromethane. The organic layers were separated, pooled, and concentrated under reduced pressure. The product was purified through flash column chromatography on a 12-gram silica gel column using a gradient of 0-100% ethyl acetate in hexanes. Product N-(5-fluoro-1,3- benzothiazol-2-yl)-3-phenoxy-N-[(pyrimidin-5-yl)methyl]propanamide (54.4 mg, 0.13 mmol, 36 %) was afforded as a white solid.1H NMR (300 MHz, Chloroform-d) δ 9.19 (s, 1H), 8.80 (s, 2H), 7.75 (dd, J = 8.7, 5.2 Hz, 1H), 7.47 (dd, J = 9.6, 2.5 Hz, 1H), 7.35 - 7.23 (m, 2H), 7.11 (td, J = 8.9, 2.5 Hz, 1H), 7.02 - 6.94 (m, 1H), 6.94 - 6.82 (m, 2H), 5.65 (s, 2H), 4.43 (t, J = 6.2 Hz, 2H), 3.15 (t, J = 6.2 Hz, 2H); LCMS (ESI) m/z: 409.0 [M+H]+.
3% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 70℃; for 16h; 242.2 Step 2: Preparation of N-(5-fluoro-1,3-benzothiazol-2-yl)-3-phenoxy-N-[(pyrimidin-5- yl)methyl]propanamide In a reaction vial, 5-fluoro-N-[(pyrimidin-5-yl)methyl]-1,3-benzothiazol-2-amine (95.9 mg, 0.37 mmol), 3-phenoxypropanoic acid (122 mg, 0.74 mmol), and triethylamine (0.26 mL, 1.8 mmol) were dissolved in dichloromethane (2 mL) with stirring. The reaction was cooled to 0 °C, and 50% propylphosphonic anhydride in ethyl acetate (0.70 mL, 0.92 mmol) was added. The reaction was warmed to room temperature and stirred for 2.5 days. The reaction was diluted with 10 mL deionized water and washed with 2x 10 mL portions of dichloromethane. The organic layers were separated, pooled, and concentrated under reduced pressure. The product was purified through flash column chromatography on a 12-gram silica gel column using a gradient of 0-100% ethyl acetate in hexanes. Product N-(5-fluoro-1,3- benzothiazol-2-yl)-3-phenoxy-N-[(pyrimidin-5-yl)methyl]propanamide (54.4 mg, 0.13 mmol, 36 %) was afforded as a white solid.1H NMR (300 MHz, Chloroform-d) δ 9.19 (s, 1H), 8.80 (s, 2H), 7.75 (dd, J = 8.7, 5.2 Hz, 1H), 7.47 (dd, J = 9.6, 2.5 Hz, 1H), 7.35 - 7.23 (m, 2H), 7.11 (td, J = 8.9, 2.5 Hz, 1H), 7.02 - 6.94 (m, 1H), 6.94 - 6.82 (m, 2H), 5.65 (s, 2H), 4.43 (t, J = 6.2 Hz, 2H), 3.15 (t, J = 6.2 Hz, 2H); LCMS (ESI) m/z: 409.0 [M+H]+.
  • 5
  • [ 876866-50-1 ]
  • N-((1H-imidazol-5-yl)methyl)-6-(cyclopropylmethoxy)benzo[d]thiazol-2-amine [ No CAS ]
  • 1-cyclopropanecarbonyl-N-[6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(1H-imidazol-5-yl)methyl]piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 70℃; for 16h; 243.2 Step 2: Preparation of 1-cyclopropanecarbonyl-N-[6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(1H- imidazol-5-yl)methyl]piperidine-4-carboxamide To a solution of N-((1H-imidazol-5-yl)methyl)-6-(cyclopropylmethoxy)benzo[d]thiazol-2-amine (38.8 mg, 0.13 mmol) in tetrahydrofuran (5 mL) were added 1-(cyclopropanecarbonyl)piperidine-4- carboxylic acid (25.0 mg, 0.13 mmol) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1- ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (72.0 mg, 0.19 mmol) and N,N- diisopropylethylamine (33.0 mg, 0.26 mmol). The reaction was stirred at 70 °C for 16 hours. The product was indicated via UPLC analysis. The reaction was filtered over Celite and the solvent was removed under the reduced pressure. Crude product was purified by prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston C1821*250mm 10µm column. The mobile phase was acetonitrile/0.01% aqueous formic acid) to give the product 1-cyclopropanecarbonyl-N- [6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(1H-imidazol-5-yl)methyl]piperidine-4-carboxamide (8.48 mg, 0.018 mmol, 14 %) as a white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 12.00 (s, 1H), 7.67-7.70 (m, 1H), 7.59 (s, 1H), 7.49-7.50 (m, 1H), 7.08 (s, 1H), 7.01-7.04 (m, 1H), 5.49 (s, 2H), 4.30-4.42 (m, 2H), 3.85 (d, J = 7.2Hz, 2H), 3.60-3.67 (m, 1H), 3.14-3.26 (m, 1H), 2.62-2.67 (m, 1H), 1.98-2.01 (m, 1H), 1.80-1.88 (m, 2H), 1.44-1.62 (m, 2H), 1.21-1.27 (m, 1H), 0.70-0.71 (m, 4H), 0.55-0.60 (m, 2H), 0.31- 0.35 (m, 2H); LCMS (ESI) m/z: 480.3 [M+H]+
14% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 70℃; for 16h; 243.2 Step 2: Preparation of 1-cyclopropanecarbonyl-N-[6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(1H- imidazol-5-yl)methyl]piperidine-4-carboxamide To a solution of N-((1H-imidazol-5-yl)methyl)-6-(cyclopropylmethoxy)benzo[d]thiazol-2-amine (38.8 mg, 0.13 mmol) in tetrahydrofuran (5 mL) were added 1-(cyclopropanecarbonyl)piperidine-4- carboxylic acid (25.0 mg, 0.13 mmol) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1- ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (72.0 mg, 0.19 mmol) and N,N- diisopropylethylamine (33.0 mg, 0.26 mmol). The reaction was stirred at 70 °C for 16 hours. The product was indicated via UPLC analysis. The reaction was filtered over Celite and the solvent was removed under the reduced pressure. Crude product was purified by prep-HPLC (the crude samples were dissolved in N,N-dimethylformamide before purification. Boston C1821*250mm 10µm column. The mobile phase was acetonitrile/0.01% aqueous formic acid) to give the product 1-cyclopropanecarbonyl-N- [6-(cyclopropylmethoxy)-1,3-benzothiazol-2-yl]-N-[(1H-imidazol-5-yl)methyl]piperidine-4-carboxamide (8.48 mg, 0.018 mmol, 14 %) as a white solid.1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 12.00 (s, 1H), 7.67-7.70 (m, 1H), 7.59 (s, 1H), 7.49-7.50 (m, 1H), 7.08 (s, 1H), 7.01-7.04 (m, 1H), 5.49 (s, 2H), 4.30-4.42 (m, 2H), 3.85 (d, J = 7.2Hz, 2H), 3.60-3.67 (m, 1H), 3.14-3.26 (m, 1H), 2.62-2.67 (m, 1H), 1.98-2.01 (m, 1H), 1.80-1.88 (m, 2H), 1.44-1.62 (m, 2H), 1.21-1.27 (m, 1H), 0.70-0.71 (m, 4H), 0.55-0.60 (m, 2H), 0.31- 0.35 (m, 2H); LCMS (ESI) m/z: 480.3 [M+H]+
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