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[ CAS No. 1092961-11-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1092961-11-9
Chemical Structure| 1092961-11-9
Chemical Structure| 1092961-11-9
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Product Details of [ 1092961-11-9 ]

CAS No. :1092961-11-9 MDL No. :MFCD11052640
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :ASOJENREUJHTMD-UHFFFAOYSA-N
M.W : 162.19 Pubchem ID :44119264
Synonyms :

Calculated chemistry of [ 1092961-11-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.12
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 1.25
Consensus Log Po/w : 1.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.76
Solubility : 2.8 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 14.3 mg/ml ; 0.0879 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.828 mg/ml ; 0.00511 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 1092961-11-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1092961-11-9 ]

* 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 [ 1092961-11-9 ]

[ 1092961-11-9 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 1092961-11-9 ]
  • [ 124-63-0 ]
  • [ 1279716-30-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃; for 3h; 14.1 Step 1: Preparation of (1-methyl-1H-indazol-5-yl)methyI methanesulfonate: (1-methyl-1H-indazol-5-yl)methanol (0.15 g, 0.92 nxmol) was dissolved in dichloromethane (3 mL), cooled to 0 °C and treated with triethylamine (0.14 mL, 1.0 mmol, 1.1 equiv) and methanesulfonyl chloride (0.079 mL, 1.0 mmol, 1.1 equiv). After stimng for 2 hours, the mixture was treated with additional triethylamine (0.14 mL, 1.0 mmol, 1.1 equiv) and methanesulfonyl chloride (0.079 mL, 1.0 mmol, 1.1 equiv). After an additional 1 hour, the mixture was diluted with dichloromethane (100 mL), washed with sodium bicarbonate (15 mL, aqueous saturated) and brine (15 mL), dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.
  • 2
  • [ 192944-51-7 ]
  • [ 1092961-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Cooling with ice
  • 3
  • [ 1314398-37-2 ]
  • [ 1092961-11-9 ]
YieldReaction ConditionsOperation in experiment
66% With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Cooling with ice; 4.1.4 (1-Methyl-1H-indazol-5-yl)methanol Step 4-1-4 (1-Methyl-1H-indazol-5-yl)methanol Lithium aluminum hydride (300 mg, 7.83 mmol) was suspended in tetrahydrofuran (20 ml); and under an ice cooling, a solution (10 ml) of ethyl 1-methyl-1H-indazole-5-carboxylate (800 mg, 3.92 mmol) prepared in the Step 4-1-3-A in tetrahydrofuran was slowly added thereto. After the mixture was stirred under an ice cooling for 30 minutes, 5 drops of a saturated sodium bicarbonate solution were slowly added to the mixture. Ethyl acetate was added to the mixture, and 5 drops of a saturated sodium bicarbonate solution was further added thereto. The precipitate was removed by filtration, and the filtrate was concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (420 mg, 66%) as a light-brown powder. 1H-NMR (CDCl3)6: 7.95 (s, 1H), 7.69 (s, 1H), 7.43-7.37 (m, 2H), 4.78 (d, J=5.8 Hz, H), 4.07 (s, 3H) Mass, m/z: 162 (M+, base)
  • 4
  • [ 2486-70-6 ]
  • [ 1092961-11-9 ]
  • 5
  • [ 40800-65-5 ]
  • [ 1092961-11-9 ]
  • 6
  • [ 192944-50-6 ]
  • [ 1092961-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water / ethanol / 15 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h 2.2: 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Cooling with ice
  • 7
  • [ 1092961-11-9 ]
  • 3-fluoro-5-(2-(3-(2-fluorobenzyloxy)-3-phenylpropylsulfonyl)-6-methylpyrimidin-4-yl)pyridin-2(1H)-one [ No CAS ]
  • 3-fluoro-5-(2-(3-(2-fluorobenzyloxy)-3-phenylpropylsulfonyl)-6-methylpyrimidin-4-yl)-1-((1-methyl-1H-indazol-5-yl)methyl)pyridin-2(1H)-one [ No CAS ]
  • 5-((3-fluoro-5-(2-(3-(2-fluorobenzyloxy)-3-phenylpropylsulfonyl)-6-methylpyrimidin-4-yl)pyridin-2-yloxy)methyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38.1% 2: 19.1% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 50℃; for 2h; Inert atmosphere; 3-fluoro-5- (2- (3- (2-fluorobenzyloxy) -3-phenylpropylsulfonyl) -6-methylpyrimidin-4-yl) -1- ( (1-methyl-1H-indazol-5-yl) methyl) pyridin-2 (1H) -one (327) and 5- ( (3-fluoro-5- (2- (3- (2-fluorobenzyloxy) -3-phenylpropylsulfonyl) -6-methylpyrimidin-4-yl) pyridin-2-yloxy) methyl) -1-methyl-1H-indazole (328) DIAD (24mg, 0.12mmol) was added to the solution of 325 (30mg, 0.06mmol) , (1-methyl-1H-indazol-5-yl) methanol (10mg, 0.06mmol) and PPh3 (30mg, 012mmol) in THF at 0 under N2. Then the reaction mixture was heated to 50 and stirred for 2h. Evaporation to remove the solvent , the residue was diluted by water , extracted by EtOAc for 3 times. The organic layer was combined , washed by brine, dried over Na2SO4, further purified by pre-TLC (PE: EA1: 1) to give the titled compounds 327 (15mg, 38.1) as light yellow solid and 328 (7mg, 19.1) as white solid. 327: 1HNMR (400 MHz, CDCl3) δ 8.31 (dd, J0.8, 2.0Hz, 1H) , 7.96 (s, 1H) , 7.74-7.69 (m, 2H) , 7.54-7.51 (m, 1H) , 7.44 (dd, J1.2, 8.8Hz, 1H) , 7.38-7.30 (m, 8H) , 7.09 (td, J0.8, 7.6Hz, 1H) , 7.00 (m, 1H) , 5.34 (m, 2H) , 4.55 (m, 1H) , 4.49 (d, J12.0Hz, 1H) , 4.36 (d, J12.0Hz, 1H) , 4.05 (s, 3H) , 3.78-3.72 (m, 1H) , 3.60-3.52 (m. 1H) , 2.59 (s, 3H) , 2.36-2.20 (m, 2H) . Mass (m/z) : 656.41 [M+H] +. 328: 1HNMR (400 MHz, CDCl3) δ 8.68 (d, J2.0, 1H) , 8.13 (dd, J2.0, 10.4Hz, 1H) , 7.99 (m, 1H) , 7.88 (m, 1H) , 7.73-7.69 (m, 1H) , 7.63 (s, 1H) , 7.57-7.51 (m, 2H) , 7.49-7.30 (m, 6H) , 7.12 (td, J1.2, 7.6Hz, 1H) , 7.01 (m, 1H) , 5.66 (s, 2H) , 4.59 (m, 1H) , 4.52 (d, J12.0Hz, 1H) , 4.39 (d, J12.0Hz, 1H) , 4.09 (s, 3H) , 3.85-3.77 (m, 1H) , 3.66-3.59 (m, 1H) , 2.68 (s, 3H) , 2.40-2.26 (m, 2H) . Mass (m/z) : 656.51 [M+H] +.
  • 8
  • [ 1092961-11-9 ]
  • 5-((2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrrolidin-1-yl)methyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 - 20 °C 2: triethylamine / acetonitrile / 20 °C
  • 9
  • [ 1092961-11-9 ]
  • 5-(chloromethyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In dichloromethane at 0 - 20℃; for 3h; Intermediate 15: 5-(chloromethyl)-1 -methyl-1 H-indazole To a stirred solution of (1 -methyl-1 H-indazol-5-yl)methanol (0.15 g, 9.0 mmol)) in dry DCM (3 mL), SOCI2 (0.2 mL, 2.8 mmol) was added at 0°C and the mixture was stirred for 3 h at RT. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under vacuum. The resulting crude product was co-distilled with DCM (2 x 10 mL) to afford the title compound. It was used in the next step without any further purification. Yield: 71 % (120 mg, pale yellow solid). 1H NMR: (400 MHz, CDCb-de): d 8.01 (s, 1 H), 7.76 (s, 1 H), 7.49 (d, J = 1.6 Hz, 2H), 4.76 (s, 2H), 4.1 1 (s, 3H).
  • 10
  • [ 2875-18-5 ]
  • [ 1092961-11-9 ]
  • 1-methyl-5-((3,5,6-trifluoropyridin-2-yl)oxy)methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.9% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 24h; 4.A Step A: Synthesis of 1-methyl-5-((3,5,6-trifluoropyridin-2-yl)oxy)methyl-1H-indazole At room temperature, (1-methyl-1H-indazol-5-yl)methanol (322.0 mg, 2.0 mmol), tetrafluoropyridine (0.6 g, 6.0 mmol),Potassium carbonate (830.0 mg, 6.0 mmol) was dissolved and added to N-methylpyrrolidone (10 mL). The temperature was raised to 110 degrees Celsius and the reaction was carried out for 24 hours. After the reaction was completed, the reaction solution was filtered through celite, and the obtained filtrate was concentrated under reduced pressure.The mixture was diluted with ethyl acetate (150 mL), washed with water (30 mL×L), saturated brine (50 mL×L), dried over anhydrous sodium sulfate, and finally concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10/1) to obtain 300.5 mg of yellow solid 1-methyl-5-(((3,5,6-trifluoropyridine- 2-yl)oxy)methyl-1H-indazole (yield: 48.9%).
  • 11
  • [ 1092961-11-9 ]
  • methyl 2-(6-(3,5-difluoro-6-((1-methyl-1H-indazol-5-yl)methoxy)pyridin-2-yl)-6-azaspiro[2.5]octan-1-yl)-1-((S)-oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 24 h / 110 °C 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
  • 12
  • [ 1092961-11-9 ]
  • 2-(6-(3,5-difluoro-6-((1-methyl-1H-indazol-5-yl)methoxy)pyridin-2-yl)-6-azaspiro[2.5]octan-1-yl)-1-((S)-oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 24 h / 110 °C 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; ethanol / 24 h / 20 °C
  • 13
  • [ 1092961-11-9 ]
  • methyl 2-(-6-(5-fluoro-4-((1-methyl-1H-indazol-5-yl)methoxy)pyrimidin-2-yl)-6-azaspiro[ 2.5]octan-1-yl)-1-((S)-oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
  • methyl 2-(-6-(5-fluoro-4-((1-methyl-1H-indazol-5-yl)methoxy)pyrimidin-2-yl)-6-azaspiro[ 2.5]octan-1-yl)-1-((S)-oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil / 0.5 h / 0 °C 1.2: 2 h / 0 °C 2.1: triethylamine / N,N-dimethyl-formamide / 4 h / 90 °C
  • 14
  • [ 1092961-11-9 ]
  • 4-(4-fluoro-3-((1-methyl-1H-indazol-5-yl)methoxy)phenyl)-3,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 20 °C / Cooling with ice 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 2 h / Inert atmosphere
  • 15
  • [ 1092961-11-9 ]
  • 5-((2-fluoro-5-(1,2,3,6-tetrahydropyridin-4-yl)phenoxy)methyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 20 °C / Cooling with ice 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 2 h / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Cooling with ice
  • 16
  • [ 1092961-11-9 ]
  • methyl (S)-2-((4-(4-fluoro-3-(1-methyl-1H-indazol-5-ylmethoxy)phenyl)-3,6-dihydropyridin-1(2H)-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 20 °C / Cooling with ice 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 2 h / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Cooling with ice 4: Cs2CO3 / N,N-dimethyl-formamide / 2 h / 60 °C
  • 17
  • [ 1092961-11-9 ]
  • (S)-2-((4-(4-fluoro-3-((1-methyl-1H-indazol-5-yl)methoxy)phenyl)-3,6-dihydropyridin-1(2H)-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 20 °C / Cooling with ice 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 2 h / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Cooling with ice 4: Cs2CO3 / N,N-dimethyl-formamide / 2 h / 60 °C 5: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C
  • 18
  • [ 1092961-11-9 ]
  • (S)-2-((4-(4-fluoro-3-((1-methyl-1H-indazol-5-yl)methoxy)phenyl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 20 °C / Cooling with ice 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 2 h / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C / Cooling with ice 4: Cs2CO3 / N,N-dimethyl-formamide / 2 h / 60 °C 5: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C 6: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 40 °C
  • 19
  • [ 1092961-11-9 ]
  • [ 2927-71-1 ]
  • 5-(((2-chloro-5-fluoropyrimidin-4-yl)oxy)methyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: (1-methyl-1H-indazol-5-yl)methanol With sodium hydride In mineral oil at 0℃; for 0.5h; Stage #2: 5-fluoro-2,4-dichloropyrimidine In mineral oil at 0℃; for 2h; 8.A Step A: Synthesis of 5-(((2-Chloro-5-fluoropyrimidin-4-yl)oxy)methyl)-1-methyl-1H-indazole (1-Methyl-1H-indazol-5-yl)methanol (750 mg, 4.63 mmol) was dissolved in N,N-dimethylformamide (20 mL) at room temperature and cooled to zero degrees Celsius.Sodium hydride (111 mg, 4.63 mmol) was added and stirred for 0.5 h, followed by 2,4-dichloro-5-fluoropyrimidine (768 mg, 4.63 mmol).The reaction was carried out in an ice bath for 2 hours. After the reaction was completed, saturated brine was added to quench the reaction, the mixture was extracted with ethyl acetate (20 ml × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, the organic phase was concentrated after filtration, and the obtained crude product was subjected to silica gel column chromatography Purification (eluent: ethyl acetate/n-hexane=1/1)850 mg of 5-((((2-chloro-5-fluoropyrimidin-4-yl)oxy)methyl)-1-methyl-1H-indazole (yield: 63%) were obtained as pale yellow oily liquid.
  • 20
  • [ 1092961-11-9 ]
  • [ 112204-58-7 ]
  • 5-((5-bromo-2-fluorophenoxy)methyl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.2% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 10h; Cooling with ice; 12.A Step A: Synthesis of 5-((5-bromo-2-fluorophenoxy)methyl)-1-methyl-1H-indazole In an ice bath, diisopropyl azodicarboxylate (130 mg, 0.65 mmol) and triphenylphosphine (1500 mg, 5.24 mmol) were added to 10 mL of dry tetrahydrofuran solvent,After stirring for 10 minutes under ice bath,Then (1-methyl-1H-indazol-5-yl)methanol (300 mg, 1.85 mmol) and 5-bromo-2-fluorophenol (386 mg, 2.04 mmol) were added respectively,After the addition was completed, the reaction was carried out at room temperature for 10 hours.After the reaction, 20 ml of ethyl acetate was added for extraction, the ethyl acetate layer was separated, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain a pale yellow solid.Purified by column chromatography (n-hexane/ethyl acetate=10/1) to obtain 310 mg of white solid 5-((5-bromo-2-fluorophenoxy)methyl)-1-methyl-1H-indazole ( Yield: 50.2%).
  • 21
  • [ 1092961-11-9 ]
  • tert-butyl (S)-2-((4-(6-chloropyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
  • tert-butyl (S)-2-((4-(6-((1-methyl-1H-indazol-5-yl)methoxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium tertiary butoxide In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; 11.A; 20.C Step A: Synthesis of tert-butyl (S)-2-((4-(6-((1-methyl-1H-indazol-5-yl)methoxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate (S)-2-(((4-(6-chloropyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H- Benzo[d]imidazole-6-carboxylate tert-butyl ester (100 mg, 0.20 mmol) was dissolved in 1,4-dioxane (10.0 mL), and (1-methyl-1H-indazole- 5-yl)methanol (40 mg, 0.24 mmol), sodium tert-butoxide (66 mg, 0.4 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl(39 mg, 0.040 mmol) mol) and tris(dibenzylideneacetone)dipalladium (27 mg, 0.020 mmol) were added to the reaction flask, and after nitrogen protection, stirred at 100 degrees Celsius for 2 hours. The reaction solution was filtered through a pad of celite, the filtrate was slowly added dropwise to a saturated aqueous ammonium chloride solution (20.0 mL), the mixture was extracted with ethyl acetate (20.0 mL × 3 times), the organic phases were combined, and the organic phase was washed with saturated common salt water (15.0 mL × 3 times), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=20/1) to obtain 80 mg of yellow solid (S)-2-((4-(6-((((1-methyl- 1H-Indazol-5-yl)methoxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[ d] tert-butyl imidazole-6-carboxylate (yield: 64.5%).
  • 22
  • [ 1092961-11-9 ]
  • tert-butyl (S)-2-((4-(6-chloropyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
  • (S)-2-((4-(6-((1-methyl-1H-indazol-5-yl)methoxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
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