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Chemical Structure| 2222941-37-7
Chemical Structure| 2222941-37-7
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Product Details of [ 2222941-37-7 ]

CAS No. :2222941-37-7 MDL No. :MFCD32062689
Formula : C30H32F2N4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SKDNDJWEBPQKCS-RIQBOWGZSA-N
M.W : 534.60 Pubchem ID :134457551
Synonyms :
CCS1477;CBP-IN-1;Inobrodibum;CBP/p300-IN-4

Safety of [ 2222941-37-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2222941-37-7 ]

* 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 [ 2222941-37-7 ]

[ 2222941-37-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 2222941-39-9 ]
  • [ 168267-41-2 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: (S)-6-(5-(3,5-dimethylisoxazol-4-yl)-1-((1r,4S)-4-methoxycyclohexyl)-1H-benzo[d]imidazol-2-yl)piperidin-2-one; dihydroxy(3,4-difluorophenyl)borane In dichloromethane at 15 - 25℃; for 0.166667h; Large scale; Stage #2: With pyridine; Cu(OAc)2*H2O In dichloromethane at 15 - 25℃; for 16h; Large scale; 4 Example 4: Preparation of Compound (I) Reagents: Cu(0Ac)2.H20, air, dichloromethane, pyridine Compound (7) (975.4 g, 2.3lmol) and 3,4-difluorobenzene boronic acid (731.7 g,4.65mol) were charged to a suitable reaction vessel, followed by dichloromethane (8800 mL) and the mixture was stirred at 15 to 25 °C for 10 minutes. Pyridine (1800 mL) was added, keeping the temperature below 30°C (exothermic), followed by dichloromethane (490 mL, line rinse) and finally, Cu(0Ac)2.H20 (477.8 g, 1.03 eq.). Filtered air was passed over the reaction mixture, which was stirred at 15 to 25 °C for at least 16 hours, until the reaction was judged complete. The reaction was quenched by addition of purified water (9750 mL) below 30°C and stirred for 5 minutes. The layers were separated and the aqueous phase was extracted with dichloromethane (4920 mL).The combined organic extracts were washed with 0.1M Na2EDTA.2H20 solution (2 x 5000ml) and 1M hydrochloric acid (4 x 5000mL). A check on the pH (target <2) confirmed that all of the pyridine had been removed. The organic layer was then washed with 1.0 M Na2C03 solution (5020 mL & 5040 mL) and l3%w/v brine (5100 mL) then dried over Na2S04 and filtered. The organic filtrates were concentrated down to 5 volumes below 45°C, decolourising charcoal (197.6 g) was added and the mixture was stirred for at least 45 minutes at 15 to 25°C before filtration and concentration. The solvent was replaced with ethyl acetate (5000mL); added in portions, followed by evaporation. The residue was dissolved in ethyl acetate (2000mL) and heated to reflux, then -heptane (3900 mL) was added maintaining a temperature of at least 60°C, during which the product crystallised. The resulting suspension was cooled to 15 to 25°C, over 1 hour and stirred at 15 to 25 °C for 30 minutes. The product was isolated by filtration and the filter cake washed with n-hcptanc (2 x 2000 mL). The solid was dried on the filter, under nitrogen, for 4 hours until both the ethyl acetate and n-heptane content was below l.0%w/w. The yield of Compound (1) was 1073.8g 87%). Purification Crude Compound (1) (2030.5 g) and ethyl acetate (14250 mL) were heated to reflux (75 to 82°C) and the resulting solution was allowed to cool to 20°C to 40°C then filtered hot. A line rise with ethyl acetate (250 mL) followed and the combined filtrates were heated to reflux (75 to 82°C). After stirring at reflux for 5 minutes, n-heptane (6000 mL) was charged over 30 minutes; maintaining a temperature of at least 60°C, then adjusting to 70°C. Compound (1) seed (20.3g) was added and the mixture stirred for 5 minutes, then checked to ensure the seed remained undissolved. Further n-heptane (8000 mL) was added over 30 minutes maintaining a temperature of at least 60°C. The mixture was again heated to 70 to 82°C and stirred for 1 hour. The resulting suspension was allowed to cool to 15 to 25 °C over a period of up to 24 hours and the product was isolated by filtration. The filter cake was washed with n- heptane (2 x 2000 mL) and the solid on the filter was transferred to a vacuum oven and dried under vacuum for 4 hours, until both the ethyl acetate and n-heptane content was below 0.35%w/w. The weight of Compound (1) obtained was l822.4g, (90%) 5(CDCl ; 400 MHz): 1.25-1.45, 1.88-1.89, 2.21-2.43 (m, 12H, 6 x CH2,); 2.30 (s, 3H, CHs-het); 2.43 (s, 3H, CH3-het); 2.67 (m, 1H, CH(H)-CO); 2.83 (m, 1H, CH(H)-CO); 3.29 (m, 1H, CHOMe); 3.39 (s, 3H, CH 0); 4.05 (m, 1H, CH-N); 5.26 (m, 1H, HC-NC=0); 6.95-7.05 (m, 4H, Ar-H); 7.48 (d,lH, Ar-H); 7.67 (m,lH, Ar-H)ppm
76.2% Stage #1: (S)-6-(5-(3,5-dimethylisoxazol-4-yl)-1-((1r,4S)-4-methoxycyclohexyl)-1H-benzo[d]imidazol-2-yl)piperidin-2-one With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.166667h; Stage #2: With [Cu(OH)*TMEDA]2Cl2 In dichloromethane at 20℃; for 0.166667h; Stage #3: dihydroxy(3,4-difluorophenyl)borane With oxygen In dichloromethane at 20℃; for 5h; 5.1.5 General Procedure for synthesis of target compounds General procedure: 8a-8q (0.3mmol) was dissolved in DCM (10mL), to which was added DBU (100.5mg, 0.66mmol) at room temperature. After stirring at room temperature for 10min, CuTMEDA (27.9mg, 0.06mmol) was added, and after stirring at room temperature for another 10min, substituted aromatic boronic acids 9a-9i (0.6mmol) was added to the system. The reaction was stirred at room temperature for 5h under O2 atmosphere. After the reaction was completed, the reaction mixture was diluted with DCM (25mL). The organic layer was washed with 1M HCl solution, brine, dried with anhydrous Na2SO4, filtered and concentrated under vacuum to obtain the crude products. The crude product was purified by flash chromatography to provide the target compounds. 5.1.5.1 (S)-1-(3,4-difluorophenyl)-6-(5-(3,5-dimethylisoxazol-4-yl)-1-(trans-4-methoxycyclohexyl)-1H-benzo[d]imidazol-2-yl)piperidin-2-one (A1) Refer to the General Procedure for synthesis in 5.1.5. 76.2% isolated yield; white solid. 1H NMR (600MHz, MeOD) δ 7.74 (d, J=8.5Hz, 1H), 7.64-7.59 (m, 1H), 7.27 (ddd, J=11.4, 7.2, 2.4Hz, 1H), 7.21-7.19 (m, 1H), 7.17 (dd, J=10.3, 8.8Hz, 1H), 7.08-7.00 (m, 1H), 5.71 (t, J=5.4Hz, 1H), 4.43-4.28 (m, 2H), 3.46-3.41 (m, 1H), 3.41 (s, 2H), 2.79 (dt, J=17.7, 5.8Hz, 1H), 2.64 (ddd, J=17.9, 8.2, 6.5Hz, 1H), 2.53-2.44 (m, 1H), 2.42 (s, 2H), 2.41-2.35 (m, 1H), 2.31-2.28 (m, 1H), 2.26 (s, 2H), 2.26-2.23 (m, 1H), 2.22-2.15 (m, 3H), 2.03-1.95 (m, 1H), 1.90 (d, J=12.6Hz, 1H), 1.49 (ddd, J=24.3, 13.0, 3.8Hz, 1H), 1.45-1.36 (m, 1H), 1.30-1.19 (m, 2H). 13C NMR (150MHz, MeOD) δ 171.65, 164.94, 158.51, 152.76, 142.33, 131.55, 123.83, 123.70, 123.24, 118.82, 116.84, 116.72, 116.45, 116.28, 116.02, 112.53, 77.17, 56.39, 54.52, 54.29, 31.66, 31.22, 29.89, 29.74, 28.35, 27.86, 16.93, 9.35, 8.67. HRMS (ESI): m/z Calcd for C30H32F2N4O3 [M+H]+ 535.2515, found 535.2513.
28% With di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 18h; 152 (S)-6-(5-(3,5-dimethylisoxazol-4-yl)-l-((lr,4S)-4-methoxycyclohexyl)-lH- benzo[< |imidazol-2-yl)-l-(3,4-difluorophenyl)piperidin-2-one DBU (0.080 mL, 0.531 mmol) was added to a solution of (5)-6-(5-(3,5- dimethylisoxazol-4-yl)-l-((lr,4,S)-4-methoxycyclohexyl)-lH-benzo[
  • 2
  • [ 2222941-38-8 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / 24 h / 80 °C 2: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
  • 3
  • [ 2222938-94-3 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ammonia; sodium dihydrosulfite / water monomer; tetrahydrofuran / 2 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 3: acetic acid / 24 h / 80 °C 4: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
Multi-step reaction with 3 steps 1.1: ammonium hydroxide; sodium dihydrosulfite; water monomer / tetrahydrofuran / 1 h / 20 °C 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2.2: 20 h / 80 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 3.2: 0.17 h / 20 °C 3.3: 5 h / 20 °C
  • 4
  • [ 2222938-95-4 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 2: acetic acid / 24 h / 80 °C 3: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 1.2: 20 h / 80 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 2.2: 0.17 h / 20 °C 2.3: 5 h / 20 °C
  • 5
  • [ 1428368-75-5 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran / 84 h / 60 °C 2: ammonia; sodium dihydrosulfite / water monomer; tetrahydrofuran / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 4: acetic acid / 24 h / 80 °C 5: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 5 h / 80 °C / Inert atmosphere 2.1: ammonium hydroxide; sodium dihydrosulfite; water monomer / tetrahydrofuran / 1 h / 20 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 3.2: 20 h / 80 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 4.2: 0.17 h / 20 °C 4.3: 5 h / 20 °C
  • 6
  • [ 16114-47-9 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 18 h / 90 °C 2: triethylamine / tetrahydrofuran / 84 h / 60 °C 3: ammonia; sodium dithionite / water; tetrahydrofuran / 2 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 5: acetic acid / 24 h / 80 °C 6: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
  • 7
  • [ 364-73-8 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; water monomer / 18 h / 90 °C 2: triethylamine / tetrahydrofuran / 84 h / 60 °C 3: ammonia; sodium dihydrosulfite / water monomer; tetrahydrofuran / 2 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 20 °C 5: acetic acid / 24 h / 80 °C 6: di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 18 h / 20 °C
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile 2.1: sodium dihydrosulfite; ammonium hydroxide / water monomer; tetrahydrofuran 3.1: 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 25 °C 4.1: acetic acid / 40 - 50 °C / Large scale 5.1: potassium carbonate / toluene; 1,4-dioxane; water monomer / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 5.2: 18 h / 85 - 95 °C / Large scale 6.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 6.2: 16 h / 15 - 25 °C / Large scale
Multi-step reaction with 5 steps 1.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane; water monomer / 10 h / 80 °C / Inert atmosphere 2.1: potassium carbonate / acetonitrile / 5 h / 80 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium dihydrosulfite; water monomer / tetrahydrofuran / 1 h / 20 °C 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 4.2: 20 h / 80 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 5.2: 0.17 h / 20 °C 5.3: 5 h / 20 °C
  • 8
  • [ 61367-41-7 ]
  • (S)-6-(5-(3,5-dimethylisoxazol-4-yl)-1-((1r,4S)-4-methoxycyclohexyl)-1H-benzo[d]imidazol-2-yl)-1-(3,4-difluorophenyl)piperidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile 2.1: sodium dithionite; ammonium hydroxide / water; tetrahydrofuran 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 25 °C 4.1: acetic acid / 40 - 50 °C / Large scale 5.1: potassium carbonate / toluene; 1,4-dioxane; water / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 5.2: 18 h / 85 - 95 °C / Large scale 6.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 6.2: 16 h / 15 - 25 °C / Large scale
  • 9
  • [ 2222963-84-8 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium dithionite; ammonium hydroxide / water; tetrahydrofuran 2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 25 °C 3.1: acetic acid / 40 - 50 °C / Large scale 4.1: potassium carbonate / toluene; 1,4-dioxane; water / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 4.2: 18 h / 85 - 95 °C / Large scale 5.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 5.2: 16 h / 15 - 25 °C / Large scale
  • 10
  • [ 2222963-86-0 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 25 °C 2.1: acetic acid / 40 - 50 °C / Large scale 3.1: potassium carbonate / toluene; 1,4-dioxane; water / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 3.2: 18 h / 85 - 95 °C / Large scale 4.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 4.2: 16 h / 15 - 25 °C / Large scale
  • 11
  • [ 34622-39-4 ]
  • (S)-6-(5-(3,5-dimethylisoxazol-4-yl)-1-((1r,4S)-4-methoxycyclohexyl)-1H-benzo[d]imidazol-2-yl)-1-(3,4-difluorophenyl)piperidin-2-one [ No CAS ]
  • 12
  • [ 2222963-90-6 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic acid / 40 - 50 °C / Large scale 2.1: potassium carbonate / toluene; 1,4-dioxane; water / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 2.2: 18 h / 85 - 95 °C / Large scale 3.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 3.2: 16 h / 15 - 25 °C / Large scale
  • 13
  • [ 2222963-94-0 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / toluene; 1,4-dioxane; water / 1.6 h / 40 - 50 °C / Inert atmosphere; Large scale 1.2: 18 h / 85 - 95 °C / Large scale 2.1: dichloromethane / 0.17 h / 15 - 25 °C / Large scale 2.2: 16 h / 15 - 25 °C / Large scale
  • 14
  • [ 832114-00-8 ]
  • [ 2222941-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane; water monomer / 10 h / 80 °C / Inert atmosphere 2.1: potassium carbonate / acetonitrile / 5 h / 80 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium dihydrosulfite; water monomer / tetrahydrofuran / 1 h / 20 °C 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 4.2: 20 h / 80 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 5.2: 0.17 h / 20 °C 5.3: 5 h / 20 °C
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