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[ CAS No. 101601-80-3 ] {[proInfo.proName]}

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Chemical Structure| 101601-80-3
Chemical Structure| 101601-80-3
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Product Details of [ 101601-80-3 ]

CAS No. :101601-80-3 MDL No. :MFCD04114113
Formula : C11H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XTHJCITVHCRQRD-UHFFFAOYSA-N
M.W : 170.21 Pubchem ID :2762784
Synonyms :

Calculated chemistry of [ 101601-80-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.08
TPSA : 38.91 ?2

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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.368 mg/ml ; 0.00216 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 0.92 mg/ml ; 0.0054 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.18
Solubility : 0.0113 mg/ml ; 0.0000665 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 101601-80-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 101601-80-3 ]

* 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 [ 101601-80-3 ]

[ 101601-80-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 6298-19-7 ]
  • [ 28557-00-8 ]
  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80℃; for 8h;Inert atmosphere; General procedure: Weigh out 2-bromo-3-aminopyridine (1,500mg)With 2-methoxyphenylboronic acid (483mg, 1.1eq)Dissolved in toluene/water mixed solvent (2/1, v/v),Add potassium carbonate (1.6g, 4eq)And Pd(PPh3)4 (167mg, 0.05eq)As a catalyst,The reaction flask is at 80C under nitrogen atmosphere,The reaction was terminated after stirring for 8 hours.The solvent was distilled off under reduced pressure and extracted with ethyl acetate/water for 3 times. The ethyl acetate layer was taken out, spin-dried, and purified by silica gel column chromatography to obtain the intermediate 2-(2-methoxyphenyl)pyridine-3- Amino (310mg, yield 60%).
48% EXAMPLE 7 3-Amino-2-phenylpyridine Under a nitrogen atmosphere, in a three-neck round-bottom flask equipped with a pressure-equalizing addition funnel and a thermometer were placed 12.2 g (94.9 mmol) of 3-amino-2-chloropyridine and 1.05 L of THF. To the system were added 25.0 g (47.3 mmol) of [1,2-bis-(diphenyl-phosphino)ethane]nickel (II) chloride, and the orange slurry was stirred at room temperature for 0.5 hours. To the system were added dropwise 40 mL (120 mmol) of 3M phenylmagnesium bromide in ether (temperature of reaction mixture rose to 35 C.), and the mixture was stirred for 2 days. During this period, additional (100 mL) 3M phenylmagnesium bromide was added to the system. The reaction mixture was cooled in an ice bath, 300 mL of 1M aqueous HCl was added to the system, the layers were separated and the organic phase was extracted with 1M aqueous HCl. The HCl extracts were washed with three portions of ethyl acetate and made basic with solid NaOH. The basic solution was stirred with ethyl acetate and Celite (trademark) for 0.5 hours. The mixture was filtered, the solids were rinsed with ethyl acetate and the filtrate layers were separated. The aqueous layer was extracted with ethyl acetate and the ethyl acetate fractions were washed with brine, dried (Na2 SO4) and concentrated (rotary evaporator) to obtain 11.4 g of brown oil. The crude material was purified by flash column chromatography on silica gel using 4:1 hexanes/ethyl acetate as the eluant to obtain 7.7 g (48% yield) of the title compound as a solid; mp 59-62 C.; [lit: 62-64 C. Can. J. Chem. 38, 2152 (1960)]. Anal. Calc'd for C11 H10 N2: C, 77.62; H, 5.92; N, 16.46. Found: C, 77.30; H, 5.99; N, 16.57.
91%Spectr. With palladium diacetate; In water; at 100℃; for 4h;Inert atmosphere; General procedure: A mixture of A -X (as provided in Table 3, 10 mmol, 1.0 equiv), phenylboronic acid (as provided in Table 3), Pd(OAc)2 (0.4 mmol, 0.04 equiv) and H20 (25 mL, 1384 mmol) in a 3 -neck round-bottom flask was stirred under reflux at 100 C in a N2 atmosphere for the time listed in Table 1. The initial and final pH values of the aqueous phase were measured before and after the heating was enabled when the temperature was stabilized at 25 - 27 C, and listed in Table 3. The initial reaction time (t = 0) was taken when the reaction mixture reached an internal temperature of 100 C; the time to reach this temperature was approximately 20 - 30 minutes. The reactions were biphasic with an aqueous phase and a solid phase. The cooled reaction mixture was basified to pH > 12 using 30% NaOH aqueous solution, and then was thoroughly extracted with ethyl acetate. The combined organic phase is dried over anhydrous MgSC , filtered, and then concentrated in vacuo. The crude product was analyzed by GC and 1H NMR, as provided in Table 3.
  • 3
  • [ 6298-19-7 ]
  • [ 98-80-6 ]
  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate; benzaldehyde; triphenylphosphine;palladium diacetate; In water; toluene; A solution of palladium acetate (224.5 mg, 1.00 mmol) and triphenylphosphine (1.05 g, 4.00 mmol) in toluene (1000 mL) was stirred at room temperature for 15 minutes. Phenylboronic acid (114 g, 935 mmol), 2-chloro-3-aminopyridine (100 g, 778 mmol), benzaldehyde (83.4 g, 786 mmol), and toluene (500 mL) were then added followed by a solution of sodium carbonate (200 g, 1.89 mol) in water (1500 mL). The mixture was heated to reflux for 18 hours, cooled to room temperature, and the layers were separated. The organic layer was washed with water (500 mL) and 2.5M aqueous hydrochloric acid was added (630 mL). The aqueous layer was separated and washed with toluene (300 mL). The pH was adjusted to 12-13 using 50% aqueous sodium hydroxide and the mixture was extracted with methyl-tert-butyl ether (500 mL). The organic layer was concentrated and the product was crystallized from diisopropyl ether to afford 2-phenyl-3-aminopyridine (128 g, 97% yield). M. p.=67-68 C. 1H NMR (300 MHz, CDCl3) δ3.88 (bs, 2), 7.02-7.11 (m, 2). 7.28-7.53 (m, 3), 7.67-7.71 (m, 2), 8.,13-8.16 (m, 1). 13C NMR (100 MHz, CDCl3) δ122.57, 122.96, 128.14, 128.38, 128.72, 138.54, 139.86, 139.93, 144.93.
88% With potassium phosphate; tetrabutylammomium bromide; In water; at 90℃; for 6h;Green chemistry; General procedure: To a 10-mL reaction vial, heteroaryl halide (1.0 mmol), boronic acid (1.2 mmol), K3PO4 (2.0 mmol), tetra-butylammonium bromide (TBAB) (0.5 mmol), and 4 (0.1 mol %) in water (3.5 mL) were added. The reaction mixture was stirred at 85 C and the reaction progress was monitored by GC-MS analysis. After completion of the reaction, it was diluted with H2O and CH2Cl2. The organic layer was separated from mixture, the dried organic layer over MgSO4, and evaporated under reduced pressure. The crude reaction product was purified using column chromatography on silica-gel to afford the corresponding product with isolated yield up to 98%.
71% General procedure: 3-Amino-2-chloropyridine (0.5g, 3.9mmol), phenylboronic acid (0.47 g, 3.9 mmol), and bis(triphenylphosphine)palladium dichloride (0.137 g, 0.195 mmol) were added to 1,4-dioxane (20ml). Under nitrogen atmosphere the mixture was stirred at room temperature for 30 minutes. 1M aqueous sodium carbonate (8 ml) was poured in, and the temperature was raised to 80C. After the reaction at 80C for 8 hours, the mixture was distilled off under reduced pressure. The residue was extracted with addition of ethyl acetate and water. The impurities were filtered off from the organic layer, and the solvent was distilled off under reduced pressure. The purification by column chromatography gave the title compound (0.47 g, 71.0% yield).
  • 4
  • [ 3262-89-3 ]
  • [ 6298-19-7 ]
  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;palladium diacetate; triphenylphosphine; In water; toluene; for 4h;Heating / reflux; 1.05 g (4 mmols) of triphenyl phosphine, 0.224 g (1 mmol) of palladium acetate and 750 ml of toluene were fed into a 3000-ml reactor equipped with a thermometer, a condenser and a stirrer, and stirred at 20 C. for 15 minutes. Next, 96.8 g (0.933 mols) of triphenylboroxine, 100.0 g (0.778 mols) of 3-amino-2-chloropyridine, and 950.0g (1.9 mols) of aqueous 21% sodium carbonate solution were fed into the reactor. The mixed slurry was heated and stirred at its boiling point for 4 hours. The reaction liquid was cooled to room temperature, and subjected to liquid-liquid separation to remove the aqueous layer. The toluene layer was washed with 200 g of water and then concentrated under reduced pressure to obtain 3-amino-2-phenylpyridine (purity 97.0%). [0036] 20 g of the thus-obtained 3-amino-2-phenylpyridine, 100 ml of 35% hydrochloric acid, 300 ml of water, and 20 g of 5% Pt/C (50% hydrate) were put into a 1000-ml glass autoclave, and stirred in a hydrogen atmosphere at about 30 C. under a pressure of 0.3 to 0.4 MPa for 13 hours. After the reaction, this was filtered to remove the catalyst. The filtrate was adjusted to have a pH of 12 with aqueous 48% sodium hydroxide solution added thereto, and then extracted with 300 ml of chloroform. The aqueous layer was removed through liquid-liquid separation, and the chloroform layer was concentrated to obtain 19.4 g of oily, racemic cis-3-amino-2-phenylpiperidine. Its chemical purity was 82.4%. [0037] 5.71 g (26.7 mmols) of the thus-obtained racemic cis-3-amino-2-phenylpiperidine, 8.16 g (26.7 mmols) of N-benzenesulfonyl-L-phenylalanine, and 22.6 g of methanol were fed into a 100-ml flask equipped with a stirrer, a thermometer and a condenser. This was heated at 50 to 55 C., and stirred for 1 hour at the temperature, and then cooled to 20 C. over a period of about 2 hours. The precipitated crystal was taken out through filtration, and dried to obtain 5.36 g of a salt. In the salt, the content of 3-amino-2-phenylpiperidine was 33.9%, and the optical purity of the (2R,3R) isomer was 93% d.e. Next, 0.5 g of aqueous 48% sodium hydroxide solution, 1 ml of water and 5 ml of chloroform were added to 0.3 g of the salt, and stirred at room temperature to extract out 3-amino-2-phenylpiperidine. After liquid-liquid separation, the chloroform layer was analyzed through gas chromatography, which confirmed that the purity of 3-amino-2-phenylpiperidine was 99.4% except the solvent peak.
  • 5
  • [ 101601-80-3 ]
  • [ 58373-46-9 ]
  • 6
  • [ 101601-80-3 ]
  • [ 765310-73-4 ]
  • [ 58373-46-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;platinum on carbon; In water; at 18 - 22℃; under 4137.29 - 4654.46 Torr; for 0.5 - 7h; Demonstrates, in a pilot plant, an embodiment of the invention wherein 2-phenyl-3- aminopyridine was hydrogenated by contact with hydrogen in the presence of a 5% PT/C type 18MA catalyst. In a series of runs, approximately 8 kg of a 50% water wet catalyst paste formed of 5% PT/C type 18MA catalyst was fed into a stirred autoclave reactor (Hastelloy C). The paste was formed by admixing approximately 4kg of the dry catalyst with an amount of water commensurate yield to 50% water wet paste. Thereafter approximately 9kg of 2- phenyl-3-aminopyridine in a solution of 10% HCI/water was fed into the reactor, charged with H2 at a pressure of about 80 to about 90 psig. Reaction temperature was approximately 18 to ABOUT 22. The reaction proceeded for about 0.5 to about 7.0 hr, after which effluent from the reactor was sampled and analyzed in a HP-5 gas chromatograph (GC). An area percent report indicative of product amounts was generated. As appreciated by the artisan, a GC area percent correlates directly to amount of underlying product. In a first run, the area % for the desired product 2-phenyl-3-aminopiperidine was about 87.9% whereas that for the unwanted by-product of over-reduction, 2-cyclohexyl-3- aminopiperidine, was about 3.5%. In a second run, the area % for the desired product 2-phenyl-3-aminopiperidine was about 89.2% whereas that for the unwanted by-product of over-reduction, 2-CYCLOHEXYL-3- aminopiperidine, was about 5. 1%.Comparative Example 1 Demonstrates the prior art. The same conditions as in Example 1 were employed but for the use of Catalyst A, A 5% Pt/C catalyst (not type 18MA) previously used in the art to hydrogenate <strong>[101601-80-3]2-phenyl-3-aminopyridine</strong> to form 2-PHENYL-3-AMINOPIPERIDINE. GC values and area percent were assessed as in Example 1. In A first comparative run, the area % for the desired product 2-PHENYL-3- aminopiperidine was about 83. 2% WHEREAS THAT for the unwanted by-product of over- reduction, 2-CYCLOHEXYL-3-AMINOPIPERIDINE, was ABOUT 10. 2%. In a second comparative run, the area % for the desired product 2-phenyl-3- aminopiperidine was about 84. 5% whereas that for the unwanted by-product of over- reduction, 2-CYCLOHEXYL-3-AMINOPIPERIDINE, was about 9. 1%. The above results show A dramatic decrease in unwanted by-product via the inventive process as well as a concurrent increase in product yield. That is, in the inventive embodiment exemplified, the undesired production of 2-CYCLOHEXYL-3-AMINOPIPERIDINE impurity was reduced by over 50% on average whereas at the same time the sought-after product, 2- phenyl-3-aminopiperidine, showed an increase in overall yield.
  • 7
  • [ 101601-80-3 ]
  • cis-(+/-)-2-phenylpiperidin-3-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;platinum on carbon; In water; at 30℃; under 2250.23 - 3000.3 Torr; for 13h; 1.05 g (4 mmols) of triphenyl phosphine, 0.224 g (1 mmol) of palladium acetate and 750 ml of toluene were fed into a 3000-ml reactor equipped with a thermometer, a condenser and a stirrer, and stirred at 20 C. for 15 minutes. Next, 96.8 g (0.933 mols) of triphenylboroxine, 100.0 g (0.778 mols) of 3-amino-2-chloropyridine, and 950.0g (1.9 mols) of aqueous 21% sodium carbonate solution were fed into the reactor. The mixed slurry was heated and stirred at its boiling point for 4 hours. The reaction liquid was cooled to room temperature, and subjected to liquid-liquid separation to remove the aqueous layer. The toluene layer was washed with 200 g of water and then concentrated under reduced pressure to obtain <strong>[101601-80-3]3-amino-2-phenylpyridine</strong> (purity 97.0%). [0036] 20 g of the thus-obtained <strong>[101601-80-3]3-amino-2-phenylpyridine</strong>, 100 ml of 35% hydrochloric acid, 300 ml of water, and 20 g of 5% Pt/C (50% hydrate) were put into a 1000-ml glass autoclave, and stirred in a hydrogen atmosphere at about 30 C. under a pressure of 0.3 to 0.4 MPa for 13 hours. After the reaction, this was filtered to remove the catalyst. The filtrate was adjusted to have a pH of 12 with aqueous 48% sodium hydroxide solution added thereto, and then extracted with 300 ml of chloroform. The aqueous layer was removed through liquid-liquid separation, and the chloroform layer was concentrated to obtain 19.4 g of oily, racemic cis-3-amino-2-phenylpiperidine. Its chemical purity was 82.4%. [0037] 5.71 g (26.7 mmols) of the thus-obtained racemic cis-3-amino-2-phenylpiperidine, 8.16 g (26.7 mmols) of N-benzenesulfonyl-L-phenylalanine, and 22.6 g of methanol were fed into a 100-ml flask equipped with a stirrer, a thermometer and a condenser. This was heated at 50 to 55 C., and stirred for 1 hour at the temperature, and then cooled to 20 C. over a period of about 2 hours. The precipitated crystal was taken out through filtration, and dried to obtain 5.36 g of a salt. In the salt, the content of 3-amino-2-phenylpiperidine was 33.9%, and the optical purity of the (2R,3R) isomer was 93% d.e. Next, 0.5 g of aqueous 48% sodium hydroxide solution, 1 ml of water and 5 ml of chloroform were added to 0.3 g of the salt, and stirred at room temperature to extract out 3-amino-2-phenylpiperidine. After liquid-liquid separation, the chloroform layer was analyzed through gas chromatography, which confirmed that the purity of 3-amino-2-phenylpiperidine was 99.4% except the solvent peak.
  • 8
  • sodium hydroxide (NaOH) [ No CAS ]
  • [ 7440-44-0 ]
  • [ 101601-80-3 ]
  • [ 7440-06-4 ]
  • [ 58373-46-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; A. 3-Amino-2-phenylpiperidine A 500 ml Parr bottle was charged with 5 grams of 5% platinum/carbon (50% water wet), 5 grams (0.0293 mol.) <strong>[101601-80-3]3-amino-2-phenylpyridine</strong> (1 equivalent), 75 ml of water (15 vol.) and 25 ml of concentrated hydrochloric acid (5 vol.). The reaction was hydrogenated (maintaining the hydrogen pressure between 36 psi and 50 psi) until high pressure liquid chromatography (HPLC) indicated complete reaction. The catalyst was removed by filtration and the pH of the filtrate was adjusted from 0 to a stable 11.2 using 25% sodium hydroxide (NaOH). The aqueous layer was extracted twice with 50 ml of methylene chloride (CH2Cl2). The organic extracts were combined, dried with magnesium sulfate (MgSO4) and the filtrate was atmospherically distilled to an oil, 4.34 grams (84.1%).
  • 9
  • [ 6298-19-7 ]
  • 3-(N-Benzylideneamino)-2-chloropyridine [ No CAS ]
  • [ 98-80-6 ]
  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; sodium carbonate; benzaldehyde;tetrakis(triphenylphosphine)palladium (0); In water; toluene; To 2-chloro-3-aminopyridine (1.06 g, 8.24 mmol) in toluene (25 mL) was added benzaldehyde (0.878 g, 8.27 mmol). The reaction mixture was stirred at reflux in a Dean-Stark apparatus until GC/MS analysis of the reaction mixture no longer showed starting material. The reaction mixture was cooled to room temperature and the toluene solution containing benzylidene-(2-chloro-pyridin-3-yl)-amine was added to a mixture of phenylboronic acid (1.30 g, 10.7 mmol), sodium carbonate (2.66 g, 25.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (47 mg, 0.38mol %) in water (10 mL). The reaction mixture was heated to 100 C. for 30 minutes, cooled to room temperature and poured into 1N aqueous sodium hydroxide (10 mL). The aqueous layer was removed and the toluene layer was extracted with 1N aqueous hydrochloric acid (twice with 15 mL). The aqueous layer was neutralized to pH 12 with 6N aqueous sodium hydroxide and extracted with MTBE (twice with 20 mL). The MTBE extracts were dried over magnesium sulfate, filtered and concentrated to afford 2-phenyl-3-aminopyridine as a solid which crystallized from diisopropyl ether (1.26 g, 90% yield). M. p.=87-68 C. 1H NMR (300 MHz, CDCl3) δ3.88 (bs, 2), 7.02-7.11 (m, 2), 7.28-7.53 (m, 3), 7.6714 7.71 (m, 2), 8.13-8.16 (m, 1). 13C NMR (100 MHz, CDCl3) δ122.57, 122.96, 128.14, 128.38, 128.72, 138.54, 139.86, 139.93, 144.93.
  • 10
  • C18H14N2 [ No CAS ]
  • [ 101601-80-3 ]
  • 11
  • [ 15761-39-4 ]
  • [ 101601-80-3 ]
  • C21H25N3O3 [ No CAS ]
  • 12
  • [ 134896-35-8 ]
  • [ 101601-80-3 ]
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; ;