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Structure of 1215767-86-4

Chemical Structure| 1215767-86-4

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Product Details of [ 1215767-86-4 ]

CAS No. :1215767-86-4
Formula : C9H5BrClN
M.W : 242.50
SMILES Code : ClC1=CC=CC2=C1C=NC=C2Br
MDL No. :MFCD16658749
InChI Key :AMMJKPXUAMAVCA-UHFFFAOYSA-N
Pubchem ID :58349499

Safety of [ 1215767-86-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1215767-86-4 ]

* 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 [ 1215767-86-4 ]

[ 1215767-86-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 34784-07-1 ]
  • [ 1215767-86-4 ]
YieldReaction ConditionsOperation in experiment
37% With N-Bromosuccinimide; acetic acid; at 50℃; for 0.666667h; To a solution of 8-chloroisoquinoline (5.00 g, 30.5 mmol, CASNo. 34784-07-1) in AcOH (50 mL) was added NBS (7.07 g, 39.7 mmol), then the reaction mixture was stirred at 50 C for 40 min. On completion, the reaction mixture was diluted with water (100 mL), then extracted with EA (3 X 80mL). The combined organic layer was basified with NaHCO3 until the pH = 6 - 7, then the mixture was extracted with EA (2 X 60 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, PE : EA=100 : 1 to PE : EA = 50 : 1, PE : EA = 10 : 1, PI : R/= 0.74) to give the title compound (1.00 g, 37% yield) as yellow solid. 1H NMR (400 MHz, CDCl3) δ 9.56 (s, 1H), 8.78 (s, 1H), 8.10 - 8.03 (m, 1H), 7.73 - 7.64 (m, 2H). LC-MS (ESI+) m/z 241.9 (M+H)+.
37% With N-Bromosuccinimide; acetic acid; at 50℃; for 0.666667h; To a solution of 8-chloroisoquinoline (5.00 g, 30.5 mmol, CASNo. 34784-07-1) in AcOH (50 mL) was added NBS (7.07 g, 39.7 mmol), then the reaction mixture was stirred at 50 C for 40 min. On completion, the reaction mixture was diluted with water (100 mL), then extracted with EA (3 X 80mL). The combined organic layer was basified with NaHCO3 until the pH = 6 - 7, then the mixture was extracted with EA (2 X 60 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, PE : EA=100 : 1 to PE : EA = 50 : 1, PE : EA = 10 : 1, PI : R/= 0.74) to give the title compound (1.00 g, 37% yield) as yellow solid. 1H NMR (400 MHz, CDCl3) δ 9.56 (s, 1H), 8.78 (s, 1H), 8.10 - 8.03 (m, 1H), 7.73 - 7.64 (m, 2H). LC-MS (ESI+) m/z 241.9 (M+H)+.
INTERMEDIATE 10 . 4-BROMO-8-CHLOROISOQUINOLINE25 To a solution of 8-chloroisoquinoHne (1.0 g, 6.1 mmol) in nitrobenzene (20 mL) at 18O0C was added bromine (0.35 mL, 6.7 mmol) over 10 min. Heating and stirring were continued for 2 hours. The mixture was allowed to cool to about 8O0C5 then 2M HCl in Et2O (5 mL) was added, followed by Et2O (5 mL) and hexanes (60 mL). The resulting slurry was filtered, washed with hexane and dried. The collected solid was dissolved in water, then the30 solution was adjusted to pH 9 with Na2CO3 (aq). The solution was extracted with EtOAc. The 3VfRL DOB-00006organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 9.62 (s, 1 H); 8.83 (s, 1 H); 8.13 (t, J - 5.0 Hz, 1 H); 7.74 (d, J = 5.0 Hz, 2 H). LC6: 4.08 rain, (M+H): 242.
  • 2
  • [ 1215767-86-4 ]
  • 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione [ No CAS ]
  • 1-(8-chloro-4-isoquinolyl)-3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.06% With potassium phosphate; copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 110℃; for 8.0h; To a solution of <strong>[1215767-86-4]4-bromo-8-chloro-isoquinoline</strong> (100 mg, 412 umol) and 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (96.6 mg, 412,37 umol, Intermediate EJ) in DMF (1 mL) was added Cul (7.85 mg, 41.2 umol), (1S, 2S)-N1,N2-dimethylcyclohexane-1,2-diamine (5.87 mg, 41.2 umol) and K3PO4 (175 mg, 824 umol), then the mixture was stirred at 110 C for 8 hr. On completion, the reaction mixture was filtered and concentrated in vacuo to give the residue. The residue was diluted with water (50 mL) and extracted with EA (5 X 30 mL). Then the combined organic layers was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by reverse-phase (0.1% FA) to give the title compound (15 mg, 3.06% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.89 - 9.56 (br s, 1H), 8.59 (br s, 1H), 7.73 - 7.68 (m, 1H), 7.64 (t, J= 8.0 Hz, 1H), 7.60 - 7.55 (m, 1H), 7.43 (d, J= 8.4 Hz, 2H), 6.85 (d, J= 8.4 Hz, 2H), 5.00 (s, 2H), 3.95 - 3.86 (m, 1H), 3.80 (s, 3H), 3.78 - 3.69 (m, 1H), 3.07 - 2.99 (m, 2H); LC-MS (ESI+) m/z 396.1 (M+H)+.
3.06% With potassium phosphate; copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 110℃; for 8.0h; To a solution of <strong>[1215767-86-4]4-bromo-8-chloro-isoquinoline</strong> (100 mg, 412 umol) and 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (96.6 mg, 412,37 umol, Intermediate EJ) in DMF (1 mL) was added Cul (7.85 mg, 41.2 umol), (1S, 2S)-N1,N2-dimethylcyclohexane-1,2-diamine (5.87 mg, 41.2 umol) and K3PO4 (175 mg, 824 umol), then the mixture was stirred at 110 C for 8 hr. On completion, the reaction mixture was filtered and concentrated in vacuo to give the residue. The residue was diluted with water (50 mL) and extracted with EA (5 X 30 mL). Then the combined organic layers was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by reverse-phase (0.1% FA) to give the title compound (15 mg, 3.06% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.89 - 9.56 (br s, 1H), 8.59 (br s, 1H), 7.73 - 7.68 (m, 1H), 7.64 (t, J= 8.0 Hz, 1H), 7.60 - 7.55 (m, 1H), 7.43 (d, J= 8.4 Hz, 2H), 6.85 (d, J= 8.4 Hz, 2H), 5.00 (s, 2H), 3.95 - 3.86 (m, 1H), 3.80 (s, 3H), 3.78 - 3.69 (m, 1H), 3.07 - 2.99 (m, 2H); LC-MS (ESI+) m/z 396.1 (M+H)+.
  • 3
  • [ 1215767-86-4 ]
  • 1-(8-chloro-4-isoquinolyl)hexahydropyrimidine-2,4-dione [ No CAS ]
  • 4
  • [ 1215767-86-4 ]
  • tert-butyl 4-[2-[4-(2,4-dioxohexahydropyrimidin-1-yl)-8-isoquinolyl]ethynyl]piperidine-1-carboxylate [ No CAS ]
  • 5
  • [ 1215767-86-4 ]
  • 1-[8-[2-(4-piperidyl)ethynyl]-4-isoquinolyl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
  • 6
  • [ 1215767-86-4 ]
  • tert-butyl N-[4-[[4-[2-[4-(2,4-dioxohexahydropyrimidin-1-yl)-8-isoquinolyl]ethynyl]-1-piperidyl]methyl]cyclohexyl]carbamate [ No CAS ]
  • 7
  • [ 1215767-86-4 ]
  • 1-[8-[2-[1-[(4-aminocyclohexyl)methyl]-4-piperidyl]ethynyl]-4-isoquinolyl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
 

Historical Records

Technical Information

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[ 1215767-86-4 ]

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