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[ CAS No. 103863-15-6 ]

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Chemical Structure| 103863-15-6
Chemical Structure| 103863-15-6
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Product Details of [ 103863-15-6 ]

CAS No. :103863-15-6 MDL No. :MFCD04114112
Formula : C12H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SJLPJJGKJSOUOR-UHFFFAOYSA-N
M.W :199.21 Pubchem ID :2762789
Synonyms :

Calculated chemistry of [ 103863-15-6 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.63
TPSA : 50.19 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) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 0.5
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.195 mg/ml ; 0.000979 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.184 mg/ml ; 0.000926 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.92
Solubility : 0.0239 mg/ml ; 0.00012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 103863-15-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103863-15-6 ]

* 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 [ 103863-15-6 ]

[ 103863-15-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 3256-89-1 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
84.5% With potassium permanganate for 6h; Heating;
With potassium permanganate; water
  • 2
  • [ 103863-15-6 ]
  • [ 130943-98-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In acetic acid for 24h;
With hydrogen In methanol for 36h; E To a suspension of platinum oxide hydrate (1 g) in methanol (10 ml) was added a solution of 3- phenylpyridine-2-carboxylic acid (10.5 g, 52.8 mmol) in methanol (20 ml). The reaction was charged with 1 atm hydrogen gas and allowed to stir for 36 h. The reaction suspension was filtered and concentrated in vacuo to yield a solid residue which was dissolved in water (20 ml). To the solution were added acetone (20 ml) and sodium bicarbonate (13.3 g, 158 mmol), followed by di-/er/-butyldicarbonate (12.7 g, 58 mmol) with vigorous stirring. The resulting reaction suspension was allowed to stir for 12 h, at which point the pH was adjusted to 5.5 using IM phosphoric acid. The product was extracted with EtOAc (2 x 50 ml), and the organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield -(tert- butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid as an oily residue which crystallized on standing (8.2 g). LCMS (M+H) = 306.1.
With Adam’s catalyst; hydrogen In methanol at 20℃; 1 Step 1: 3-Phenylpiperidine-2-carboxylic acid A solution of 3-phenyl picolinic acid (1 .9949 g,10.01 mmol) in methanol (16 mE) was added to a suspension of platinum (IV) oxide hydrate (0.1956 g, 0.798 mmol) in methanol (4 mE), and the mixture was degassed and charged with hydrogen gas from a balloon. The reaction mixture was stirred for 2.25 hours at room temperature. A sample of the reaction mixture was checked by ECMS and compared to a sample of starting material. Strong peaks for the starting material and the desired product were observed along with a weak over-reduced by-product. The hydrogen balloon was removed and the reaction was flushed with nitrogen, sealed, and left overnight. In the morning, a fresh hydrogen balloon was attached and the reaction was charged and stirred for 4.5 hours at room temperature. The balloon was removed, and the reaction mixture was diluted with dichloromethane and filtered through celite resulting in removal of a black solid. The filtrate was concentrated and left under vacuum for 30 minutes to yield 3-phenylpiperidine-2-carboxylic acid (2.0188 g, 98%) as a dark brown solid. MS (ESI) mlz 206.11 (M+H). The crude product was used in subsequent steps without further purification.
  • 3
  • [ 103863-15-6 ]
  • [ 57955-12-1 ]
YieldReaction ConditionsOperation in experiment
80% With methanesulfonic acid at 80℃; for 1h; 5 <Synthesis of Intermediate 116-14> Intermediate 116-13 28.58g (143.46mmol) was dissolved in 130ml of MsOH, heated to 80 and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, washed with saturated NaHCO3 aqueous solution, and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 20.80 g of intermediate 116-14 in a yield of 80%.
40% With polyphosphoric acid for 5h; 2.2.1. Synthesis of azafluorenone (4a-d) General procedure: (a) Halopicolinic acid (2.69 g, 13.31 mmol), phenylboronic acid(2.44 g, 19.97 mmol), 2M aqueous potassium carbonate (20 mL), palladiumacetate (0.14 g, 0.62 mmol), triphenylphosphine (0.70 g,2.67 mmol), and 1,4-dioxane (50 mL) were mixed and refluxed undernitrogen for 24 h. The reaction mixture was cooled to room temperatureand added aqueous sodium hydroxide (NaOH) (1 M, 35 mL) and dichloromethane(CH2Cl2) (20 mL). The aqueous layer was acidified topH=2-3 by using citric acid (1 M) followed by extraction with Etheracetate (EtOAc). The combined organic layers were dried over magnesiumsulfate (MgSO4), filtered, and concentrated to give off the crudeproduct. A mixture of the crude product and 50 g polyphosphoric acidwas heated at 210 °C for 5 h and then stop the reaction. After themixture had cooled to 140 °C, some ice and water were added slowly todilute the mixture. Then aqueous sodium hydroxide was added to makethe pH≥7, and the aqueous layer was extracted with EtOAc. Thecombined extracts were dried with MgSO4 and concentrated to provide0.96 g. The residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate 6:1) to give the desired product.
4.2 g With PPA Heating;
  • 4
  • [ 174681-89-1 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: methyl 3-Phenylpyridine-2-carboxylate With sodium hydroxide In methanol at 20 - 50℃; for 18.5h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water Inert atmosphere;
31% Stage #1: methyl 3-Phenylpyridine-2-carboxylate With sodium hydroxide In methanol at 20 - 50℃; for 19h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 20℃; Inert atmosphere;
With sodium hydroxide In methanol at 20℃; for 1h;
Stage #1: methyl 3-Phenylpyridine-2-carboxylate With potassium hydroxide; water In ethanol at 50℃; for 2h; Stage #2: With phosphoric acid In ethanol; water D To a solution of methyl 3-phenylpyridine-2-carboxylate (61.0 g, 286 mmol) in absolute ethanol was added potassium hydroxide (32.0 g, 572 mmol). After stirring at 5O0C for 2 h, the reaction mixture was cooled and adjusted to pH -7.5 with IM phosphoric acid. The mixture was diluted with water (1 L) and extracted with EtOAc (2 x 600 ml). The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 3-phenylpyridine-2-carboxylic acid as a solid (54.7 g).

  • 5
  • [ 103863-15-6 ]
  • [ 252002-18-9 ]
  • C28H31N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-phenylpyridine-2-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.0833333h; Stage #2: 3-spiro[2,3-dihydro-1H-indene-1,4'-piperidine]-1-ylpropane-1-amine In chloroform at 20℃; for 0.5h;
  • 9
  • [ 103863-15-6 ]
  • 1-(9-hydroxy-9<i>H</i>-indeno[2,1-<i>b</i>]pyridine-9-carbonyl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: TFA / CH2Cl2 / 2 h / 20 °C
  • 10
  • [ 103863-15-6 ]
  • 1-(9-hydroxy-1-oxy-9<i>H</i>-indeno[2,1-<i>b</i>]pyridine-9-carbonyl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: meta-chloroperoxybenzoic acid / CH2Cl2 / 0 - 20 °C 7.1: TFA / CH2Cl2
  • 11
  • [ 103863-15-6 ]
  • [ 1026646-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C
  • 12
  • [ 103863-15-6 ]
  • [4-chloro-2-([1-(9-hydroxy-1-oxy-9<i>H</i>-indeno[2,1-<i>b</i>]pyridine-9-carbonyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: meta-chloroperoxybenzoic acid / CH2Cl2 / 0 - 20 °C
  • 13
  • [ 53636-56-9 ]
  • [ 103863-15-6 ]
  • 14
  • [ 98-80-6 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / 1,4-bis(diphenylphosphino)butane; bis(benzonitrile)dichloropalladium; sodium carbonate / toluene / 18 h / Heating 2: NaOH / methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol / 24 h / Reflux 2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
  • 15
  • [ 103863-15-6 ]
  • [ 130944-00-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / Adams catalyst / acetic acid / 24 h / 2585.7 Torr 2: thionyl chloride / 1.) -10 to -15 deg C, 3 h, 2.) reflux, 12 h 3: 0.85 g / lithium aluminum hydride (LAH) / diethyl ether / 24 h
  • 16
  • [ 103863-15-6 ]
  • [ 130943-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Adams catalyst / acetic acid / 24 h / 2585.7 Torr 2: thionyl chloride / 1.) -10 to -15 deg C, 3 h, 2.) reflux, 12 h
  • 17
  • [ 19842-18-3 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / H2 / Raney Ni / ethanol / 2 h / 80 °C / 72400.7 Torr 2: 70 percent / 10percent Pd/C / 0.5 h / 300 - 310 °C 3: 84.5 percent / aq. KMnO4 / 6 h / Heating
  • 20
  • [ 1131-48-2 ]
  • [ 7677-24-9 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-phenylpyridine N-oxide; trimethylsilyl cyanide With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride; sulfuric acid Heating; Further stages.;
  • 21
  • [ 103863-15-6 ]
  • (2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))dipyrrolidine-2-carboxamide dihydrochloride [ No CAS ]
  • [ 1429787-66-5 ]
YieldReaction ConditionsOperation in experiment
46.5% 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 N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 22
  • [ 62733-99-7 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 16 h / Reflux 3.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 3.2: 20 °C / pH Ca. 2 / Inert atmosphere
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 2.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 16 h / Reflux 3.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 3.2: 20 °C / pH Ca. 2 / Inert atmosphere
Multi-step reaction with 3 steps 1.1: triethylamine / 1 h / 0 - 20 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 1 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide / methanol / 18.5 h / 20 - 50 °C / Inert atmosphere 3.2: pH 2 / Inert atmosphere
  • 23
  • [ 157865-84-4 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 16 h / Reflux 2.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 2.2: 20 °C / pH Ca. 2 / Inert atmosphere
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 1 h / 90 °C / Inert atmosphere 2.1: sodium hydroxide / methanol / 18.5 h / 20 - 50 °C / Inert atmosphere 2.2: pH 2 / Inert atmosphere
  • 24
  • [ 103863-15-6 ]
  • 2-(2-(2-bromo-4-((methoxycarbonyl)amino)phenyl)-2-oxoethyl) 1-tert-butyl 3-phenylpiperidine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C
  • 25
  • [ 103863-15-6 ]
  • (E)-methyl (3-bromo-4-(2-(1-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-3-phenylpiperidin-2-yl)-1H-imidazol-4-yl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C 4: ammonium acetate / toluene / 2 h / 150 °C / Microwave irradiation 5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 6: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
  • 26
  • [ 103863-15-6 ]
  • 1-tert-butyl 2-(2-(3-(methoxycarbonyl)phenyl)-2-oxoethyl) 3-phenylpiperidine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
  • 27
  • [ 103863-15-6 ]
  • tert-butyl 2-(4-(3-(methoxycarbonyl)phenyl)-1H-imidazol-2-yl)-3-phenylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 4: ammonium acetate / toluene / 0.33 h / 20 - 150 °C / Microwave irradiation
  • 28
  • [ 103863-15-6 ]
  • methyl 3-(2-(3-phenylpiperidin-2-yl)-1H-imidazol-4-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 4: ammonium acetate / toluene / 0.33 h / 20 - 150 °C / Microwave irradiation 5: trifluoroacetic acid / dichloromethane / 1.75 h / 20 °C
  • 29
  • [ 103863-15-6 ]
  • (E)-methyl 3-(2-(1-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-3-phenylpiperidin-2-yl)-1H-imidazol-4-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 4: ammonium acetate / toluene / 0.33 h / 20 - 150 °C / Microwave irradiation 5: trifluoroacetic acid / dichloromethane / 1.75 h / 20 °C 6: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
  • 30
  • [ 103863-15-6 ]
  • 3-(2-((2S,3S)-1-((E)-3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-3-phenylpiperidin-2-yl)-1H-imidazol-4-yl)benzoic acid 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 4: ammonium acetate / toluene / 0.33 h / 20 - 150 °C / Microwave irradiation 5: trifluoroacetic acid / dichloromethane / 1.75 h / 20 °C 6: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 7: boron tribromide / dichloromethane / 20 °C
  • 31
  • [ 103863-15-6 ]
  • tert-butyl 2-((1H-indazol-5-yl)carbamoyl)-3-phenylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C
  • 32
  • [ 103863-15-6 ]
  • N-(1H-indazol-5-yl)-3-phenylpiperidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
  • 33
  • [ 103863-15-6 ]
  • (E)-1-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-N-(1H-indazol-5-yl)-3-phenylpiperidine-2-carboxamide 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide
  • 34
  • [ 103863-15-6 ]
  • 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C
  • 35
  • [ 103863-15-6 ]
  • (2S,3S)-1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: Supercritical conditions
  • 36
  • [ 103863-15-6 ]
  • tert-butyl 2-(4-(2-bromo-4-((methoxycarbonyl)amino)phenyl)-1H-imidazol-2-yl)-3-phenylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C 4: ammonium acetate / toluene / 2 h / 150 °C / Microwave irradiation
  • 37
  • [ 103863-15-6 ]
  • methyl (3-bromo-4-(2-(3-phenylpiperidin-2-yl)-1H-imidazol-4-yl)-phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C 4: ammonium acetate / toluene / 2 h / 150 °C / Microwave irradiation 5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 38
  • [ 103863-15-6 ]
  • tert-butyl 2-(4-(4-((methoxycarbonyl)amino)phenyl)-1H-imidazol-2-yl)-3-phenylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C 4: ammonium acetate / toluene / 2 h / 150 °C / Microwave irradiation 5: hydrogen; palladium on activated charcoal / ethanol / 24.5 h / 20 °C
  • 39
  • [ 103863-15-6 ]
  • N-[(2S)-2-(ethylamino)propyl]-5-(trifluoromethyl)pyrimidin-2-amine hydrochloride [ No CAS ]
  • C22H22F3N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-phenylpyridine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.166667h; Stage #2: N-[(2S)-2-(ethylamino)propyl]-5-(trifluoromethyl)pyrimidin-2-amine hydrochloride In N,N-dimethyl-formamide at 20℃; 19 Example 3 Example 3: (0364) A-4 (61 mg, 0.27 mmol) is dissolved in dry DMF (2 mL). HATU (1 12 mg, 0.30 mmol) and DIPEA (127 μΙ_, 0.74 mmol) are added and the mixture is stirred for 10 min. Then B-1 (70 mg, 0.25 mmol) is added and the reaction is stirred at RT for 3 h. The mixture is purified by preparative LCMS (using a solvent gradient H20/ACN with NH4OH). After concentration the residue is extracted with DCM. The organic phase is dried and concentrated to afford 70 mg of compound Example 3. ESI-MS: 454 [M+Na]+; HPLC (Rt): 3.52 min (method H). The following examples are prepared in analogy to the above described procedure using the corresponding acid (see Acid Intermediates) and amine (see Amine Intermediates) as described before, adjusting reaction time: overnight for Example 14, 19:
  • 40
  • [ 30683-23-9 ]
  • [ 98-80-6 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,4-dioxane; water;Reflux; Inert atmosphere; General procedure: (a) Halopicolinic acid (2.69 g, 13.31 mmol), phenylboronic acid(2.44 g, 19.97 mmol), 2M aqueous potassium carbonate (20 mL), palladiumacetate (0.14 g, 0.62 mmol), triphenylphosphine (0.70 g,2.67 mmol), and 1,4-dioxane (50 mL) were mixed and refluxed undernitrogen for 24 h. The reaction mixture was cooled to room temperatureand added aqueous sodium hydroxide (NaOH) (1 M, 35 mL) and dichloromethane(CH2Cl2) (20 mL). The aqueous layer was acidified topH=2-3 by using citric acid (1 M) followed by extraction with Etheracetate (EtOAc). The combined organic layers were dried over magnesiumsulfate (MgSO4), filtered, and concentrated to give off the crudeproduct. A mixture of the crude product and 50 g polyphosphoric acidwas heated at 210 C for 5 h and then stop the reaction. After themixture had cooled to 140 C, some ice and water were added slowly todilute the mixture. Then aqueous sodium hydroxide was added to makethe pH?7, and the aqueous layer was extracted with EtOAc. Thecombined extracts were dried with MgSO4 and concentrated to provide0.96 g. The residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate 6:1) to give the desired product.
  • 41
  • [ 103863-15-6 ]
  • C24H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyphosphoric acid / 5 h 2: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere
  • 42
  • [ 103863-15-6 ]
  • spiro[fluorene-9,9′-indeno[2,1-b]pyridine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: polyphosphoric acid / 5 h 2: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 3: acetic acid; sulfuric acid / Reflux
  • 43
  • [ 103863-15-6 ]
  • [ 31557-57-0 ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; sodium carbonate; sodium chloride In tetrahydrofuran at 80℃; for 20h; Schlenk technique; 3 Example 3: Synthesis of 2-chloro-3-phenylpyridine (2c) Weighing 3-phenylpyridine-2-carboxylic acid (56.7 mg, 0.3 mmol),Sodium carbonate (32.0 mg, 0.3 mmol), NaCl (26.3 mg, 0.45 mmol), TBHP (102 μL, 0.9 mmol) into a 25 mL of Schlenk reaction bottle, Then THF (2 mL) was added and placed in an 80 °C oil bath for 20 h. After completion of the reaction, the solvent was removed under reduced pressure and eluted with petroleum ether / ethyl acetate. The solvent was separated on a silica gel column, and the yield of 2-chloropyridine was 91%.
91% With tert-butylhypochlorite; dichloromethane; sodium hydrogencarbonate at 60℃; for 20h; Green chemistry;
  • 44
  • [ 103863-15-6 ]
  • [ 32864-29-2 ]
  • 45
  • [ 874-24-8 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid / 6 h / Reflux; Inert atmosphere 2.1: triethylamine / 1 h / 0 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 1 h / 90 °C / Inert atmosphere 4.1: sodium hydroxide / methanol / 18.5 h / 20 - 50 °C / Inert atmosphere 4.2: pH 2 / Inert atmosphere
  • 46
  • [ 103863-15-6 ]
  • [ 32511-34-5 ]
  • 3-phenyl-N-((1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% 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 N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
  • 47
  • [ 103863-15-6 ]
  • N-((1S,2S,4R,6S)-6-(4-methoxyphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-3-phenylpicolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: palladium diacetate; cesium acetate; copper(ll) bromide / tert-Amyl alcohol / 24 h / 140 °C / Inert atmosphere; Sealed tube
  • 48
  • [ 265981-13-3 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol / 24 h / Reflux 2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
  • 49
  • [ 32864-29-2 ]
  • [ 124-38-9 ]
  • [ 103863-15-6 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 2-bromo-3-phenylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: carbon dioxide In tetrahydrofuran 5 <Synthesis of Intermediate 116-13> 44.78g (191.28mmol) of Intermediate 116-12 was dissolved in 450ml of THF, maintained at -78 using a dryice-acetone bath, and 80ml (200.85mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, while measuring the reaction degree by HPLC, CO2 (g) was slowly added. After the reaction was completed, the temperature was raised to room temperature, and after the solvent was distilled, 1 L of 1HCl was added, and a saturated aqueous NaHCO 3 solution was added. After distilling THF, the resulting solid was washed with water and filtered. After drying, it was recrystallized with MC/PE to obtain 28.58 g of Intermediate 116-13 with a yield of 75%.
  • 50
  • [ 103863-15-6 ]
  • [ 6638-79-5 ]
  • N-methoxy-N-methyl-3-phenylpyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 25℃; for 3h; 31 4-Methyl-N - [4-(3-phenylpyridin-2-yl)-l ,3-thiazol-2-yl] pyridin-2-amine N-Methoxy-N-methyl-3-phenylpyridine-2-carboxamide. To a stirred solution of 3-phenylpyridine-2-carboxylic acid (1 g, 5.02 mmol) in DMF (20mL), was added EDC.HC1 (1.4 g, 9.04 mmol) and HOBt (814 mg, 6.02 mmol) followed by N,O-dimethylhydroxylamine hydrochloride (539 mg, 5.52 mmol) and TEA (1.3 ml, 10.04 mmol). The resulting mixture was stirred at 25 °C for 3h. The reaction mixture was quenched and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography to afford N-methoxy-N-methyl-3-phenylpyridine-2-carboxamide (650 mg, 53%). MS (ESI): m/z 242.7 [M+l]+.
53% With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 25℃; for 3h; 31 4-Methyl-N - [4-(3-phenylpyridin-2-yl)-l ,3-thiazol-2-yl] pyridin-2-amine N-Methoxy-N-methyl-3-phenylpyridine-2-carboxamide. To a stirred solution of 3-phenylpyridine-2-carboxylic acid (1 g, 5.02 mmol) in DMF (20mL), was added EDC.HC1 (1.4 g, 9.04 mmol) and HOBt (814 mg, 6.02 mmol) followed by N,O-dimethylhydroxylamine hydrochloride (539 mg, 5.52 mmol) and TEA (1.3 ml, 10.04 mmol). The resulting mixture was stirred at 25 °C for 3h. The reaction mixture was quenched and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography to afford N-methoxy-N-methyl-3-phenylpyridine-2-carboxamide (650 mg, 53%). MS (ESI): m/z 242.7 [M+l]+.
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