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Chemical Structure| 173206-13-8 Chemical Structure| 173206-13-8

Structure of 173206-13-8

Chemical Structure| 173206-13-8

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Product Details of [ 173206-13-8 ]

CAS No. :173206-13-8
Formula : C9H10Cl2N2O2
M.W : 249.09
SMILES Code : O=C1C(Cl)=C(Cl)C=NN1C2CCCCO2
MDL No. :MFCD14706897
InChI Key :OEDZWNISULPNLA-UHFFFAOYSA-N
Pubchem ID :10729262

Safety of [ 173206-13-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 173206-13-8 ]

* 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 [ 173206-13-8 ]

[ 173206-13-8 ] Synthesis Path-Downstream   1~2

  • 1
  • 1-[2-(difluoromethyl)phenyl]methanamine [ No CAS ]
  • [ 790667-49-1 ]
  • [ 173206-13-8 ]
  • 4-chloro-5-[(4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one [ No CAS ]
  • 4-chloro-5-[(6S)-1-[[2-(difluoromethyl)phenyl]methyl]-6-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.79%; 23.62% To a stirred mixture of <strong>[790667-49-1]ter<strong>[790667-49-1]t-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate</strong></strong> (1 g, 4.69 mmol, 1 equiv.) and 1-azido-4-nitrobenzene (1.5 g, 9.38 mmol, 2.0 equiv.) in DMF (25 mL) were added 1-[2-(difluoromethyl)phenyl]methanamine (1.0 g, 6.56 mmol, 1.4 equiv.) and Zn(OAc)2(0.9 g, 4.69 mmol, 1.0 equiv.) at room temperature. The resulting mixture was stirred for 24 h at 60 degrees Celsius. The reaction was monitored by LCMS. The crude product was purified by reverse phase flash with the following conditions (Column: XBridge Shield RP18 OBD Column 30*150mm,5um ; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 5% B to 35% B in 14 min; 254 nm; Rt: 13.5 min) to afford tert-butyl (S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5- c]pyridine-5-carboxylate and afford tert-butyl (S)-1-[[2-(difluoromethyl)phenyl]methyl]-6- methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine-5-carboxylate (1.6 g, 90.17%) as a brown oil.; To a stirred solution of (S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H- [1,2,3]triazolo[4,5-c]pyridine (500 mg, 1.32 mmol, 1 equiv.) in DCM (10 mL, 157.30 mmol, 119.05 equiv.) was added TFA(3 mL, 40.39 mmol, 30.57 equiv.) at room temperature. The resulting mixture was stirred for 2 h at room temperature. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The mixture was basified to pH 8 with saturated NaHCO3 (aq.). The crude product was purified by reverse phase flash with the following conditions (Column: XBridge Prep C18 OBD Column, 5um,19*150mm; Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 30% B to 46% B in 7 min; 220/254 nm; Rt: 6.27 min) to afford a mixture of (S)-1-[[2- (difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (140 mg, 38.07%) as a brown oil and (S)-3-[[2-(difluoromethyl)phenyl]methyl]-6-methyl- 3H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (100 mg, 27.19%) was obtained is a similar way as a brown oil.; Into a 50 mL round-bottom flask were added (4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4- methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (240 mg, 0.86 mmol, 1 equiv.) DIEA(260 mg, 2.01 mmol, 2.33 equiv.)and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3- one (257.8 mg, 1.03 mmol, 1.2 equiv.) at room temperature. The resulting mixture was stirred for 16 h at 100 degrees Celsius. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The residue was purified by Prep-TLC (PE/EtOAc 1:1) to afford 4-chloro-5-[(4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H- [1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (160 mg, 37.79%) as a brown oil and 4-chloro-5-[(6S)-1-[[2-(difluoromethyl)phenyl]methyl]-6-methyl- 1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (100 mg, 23.62%) was obtained in a similar way as a brown oil.
  • 2
  • 1-[2-(difluoromethyl)phenyl]methanamine [ No CAS ]
  • [ 790667-49-1 ]
  • [ 173206-13-8 ]
  • 4-chloro-5-[(6S)-1-[[2-(difluoromethyl)phenyl]methyl]-6-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one [ No CAS ]
  • 4-chloro-5-[(4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.77%; 89.30% To a stirred mixture of <strong>[790667-49-1]ter<strong>[790667-49-1]t-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate</strong></strong> (1 g, 4.69 mmol, 1 equiv.) and 1-azido-4-nitrobenzene (1.5 g, 9.38 mmol, 2.0 equiv.) in DMF (25 mL) were added 1-[2-(difluoromethyl)phenyl]methanamine (1.0 g, 6.56 mmol, 1.4 equiv.) and Zn(OAc)2(0.9 g, 4.69 mmol, 1.0 equiv.) at room temperature. The resulting mixture was stirred for 24 h at 60 degrees Celsius. The reaction was monitored by LCMS. The crude product was purified by reverse phase flash with the following conditions (Column: XBridge Shield RP18 OBD Column 30*150mm,5um ; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 5% B to 35% B in 14 min; 254 nm; Rt: 13.5 min) to afford tert-butyl (S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5- c]pyridine-5-carboxylate and afford tert-butyl (S)-1-[[2-(difluoromethyl)phenyl]methyl]-6- methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine-5-carboxylate (1.6 g, 90.17%) as a brown oil.; To a stirred solution of (S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H- [1,2,3]triazolo[4,5-c]pyridine (500 mg, 1.32 mmol, 1 equiv.) in DCM (10 mL, 157.30 mmol, 119.05 equiv.) was added TFA(3 mL, 40.39 mmol, 30.57 equiv.) at room temperature. The resulting mixture was stirred for 2 h at room temperature. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The mixture was basified to pH 8 with saturated NaHCO3 (aq.). The crude product was purified by reverse phase flash with the following conditions (Column: XBridge Prep C18 OBD Column, 5um,19*150mm; Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 30% B to 46% B in 7 min; 220/254 nm; Rt: 6.27 min) to afford a mixture of (S)-1-[[2- (difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (140 mg, 38.07%) as a brown oil and (S)-3-[[2-(difluoromethyl)phenyl]methyl]-6-methyl- 3H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (100 mg, 27.19%) was obtained is a similar way as a brown oil.; Into a 50 mL round-bottom flask were added (4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4- methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridine (240 mg, 0.86 mmol, 1 equiv.) DIEA(260 mg, 2.01 mmol, 2.33 equiv.)and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3- one (257.8 mg, 1.03 mmol, 1.2 equiv.) at room temperature. The resulting mixture was stirred for 16 h at 100 degrees Celsius. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The residue was purified by Prep-TLC (PE/EtOAc 1:1) to afford 4-chloro-5-[(4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H- [1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (160 mg, 37.79%) as a brown oil and 4-chloro-5-[(6S)-1-[[2-(difluoromethyl)phenyl]methyl]-6-methyl- 1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (100 mg, 23.62%) was obtained in a similar way as a brown oil.; To a stirred solution of 4-chloro-5-[(4S)-1-[[2-(difluoromethyl)phenyl]methyl]-4-methyl- 1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (200 mg, 0.41 mmol, 1 equiv.) in DCM (10 mL) was added TFA (3 mL, 40.39 mmol, 198.29 equiv.) at room temperature. The resulting mixture was stirred for 2 h at room temperature. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The crude product (150 mg) was purified by Prep-HPLC with the following conditions (Column: XBridge Prep C18 OBD Column 19×150mm 5um; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 26% B to 46% B in 7 min; 220/254 nm; Rt: 5.9 min) to afford 4-chloro-5-[(4S)-1-[[2- (difluoromethyl)phenyl]methyl]-4-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]- 2,3-dihydropyridazin-3-one (74mg,89.30%) as a white solid and 4-chloro-5-[(6S)-1-[[2- (difluoromethyl)phenyl]methyl]-6-methyl-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]- 2,3-dihydropyridazin-3-one (54.5mg,65.77%) was obtained as a white solid.
 

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