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[ CAS No. 10165-86-3 ] {[proInfo.proName]}

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Chemical Structure| 10165-86-3
Chemical Structure| 10165-86-3
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Quality Control of [ 10165-86-3 ]

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Product Details of [ 10165-86-3 ]

CAS No. :10165-86-3 MDL No. :MFCD08275010
Formula : C8H7NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BZOWIADSJYMJJJ-UHFFFAOYSA-N
M.W : 165.15 Pubchem ID :586269
Synonyms :

Calculated chemistry of [ 10165-86-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.9
TPSA : 56.26 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : -0.28
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 7.36 mg/ml ; 0.0446 mol/l
Class : Very soluble
Log S (Ali) : -1.25
Solubility : 9.25 mg/ml ; 0.056 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.04
Solubility : 1.5 mg/ml ; 0.0091 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 10165-86-3 ]

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

Application In Synthesis of [ 10165-86-3 ]

* 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 [ 10165-86-3 ]

[ 10165-86-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 872-85-5 ]
  • [ 109-97-7 ]
  • [ 10165-86-3 ]
  • 6-((5E,10Z,14Z,19Z)-10,15,20-Tri-pyridin-4-yl-porphyrin-5-yl)-nicotinic acid methyl ester [ No CAS ]
  • 2
  • [ 5470-70-2 ]
  • [ 10165-86-3 ]
YieldReaction ConditionsOperation in experiment
70% With iodine; trifluoroacetic acid; In dimethyl sulfoxide; at 160℃; for 2h; A mixture of methyl 6-methylnicotinate (5.0 g, 33.0 mmol), 12 (8.4 g, 33.2 mmol) andTFA (7.5 mL, 11.5 g, 0.1 mol) in DMSO (100 mL) was heated to 160°C for 2 h. Themixture was allowed to cool to RT and poured into a 1 N solution ofNa2S2O3 (aq.) (0.5L) solution, made alkaline using NaOH (2 N) and extracted with EtOAc (3 x 0.2 L).The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in DCM and applied on a short pad of silica. The product was eluted with EtOAc to afford the product as a yellowish solid (3.8 g, 23 mmol, 70percent).
46% A solution of 6-methyl nicotinic acid methyl ester (1.00 g, 6.62 mmol), iodine (1.68 g, 6.62 mmol), 2-iodo-2-methylpropane (0.478.g, 2.60 mmol) and trifluoroacetic acid (2.26 g, 19.8 mmol) in anhydrous DMSO was heated for 3 h at 160° C. The reaction mixture was cooled to room temperature (rt) and treated with 1 N aq. Na2S2O3 (50 mL). The reaction mixture was adjusted to pH 10 with 1 N aq. NaHCO3. The reaction mixture was extracted with ethyl acetate (3*100 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography of the residue (SiO2; 0-3percent EtOH:DCM) gave the title compound as a solid (0.506 g, 46percent).
37% With iodine; trifluoroacetic acid; In dimethyl sulfoxide; at 0 - 140℃; for 3.5h; Iodine (33.5g, 0.13mmol) and trifluoroacetic acid (35.3ml, 0.4mmol) were added to a solution of methyl 6-carboxylate-1-picoline (20g, 0.13mol) in N,N-dimethylsulfoxide (200ml) at 0°C and the mixture was stirred for 1 hourand then heated to 140°C and stirred for 2.5 hours. After being cooled to 0°C, the reaction was quenched with saturatedsodium thiosulfate solution (30ml) and stirred for 30 minutes. The aqueous layer was extracted with ethyl acetate (150ml3 3) and the organic layers were combined and washed with brine (50ml 3 2), dried over anhydrous sodium sulfate,filtered, concentrated in vacuo and the residue was purified by flash silica gel column chromatography to give the titlecompound (8g, yield 37percent). 1H NMR (400MHz, CHLOROFORM-d) ppm :10.14 (s, 1H), 9.36 (s, 1H), 8.47 (dd, J=1.3, 8.0Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 4.05 - 3.94 (s, 3H).
15% With selenium(IV) oxide; In 1,4-dioxane; at 85℃;Inert atmosphere; 250mL single-neck flask was added methyl 6-methylpyridine-3-carboxylate (10g, 66.15mmol) and 1,4-dioxane (100mL), was added under stirring selenium dioxide (14.7g, 132mmol), nitrogen heated to 85 under the protection of the reaction overnight. Cooling to room temperature, filtered, and the solvent was removed by rotary evaporation, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1), give a pale yellow solid 1.6g, Yield: 15percent.
With iodine; dimethyl sulfoxide; at 160℃; for 0.25h; 6-Methyl-nicotinic acid methyl ester (5.00 g, 33.1 mmol) was mixed with iodine (8.40 g, 33.1 mmol) and a small amount of DMSO was added to promote mixing. After addition of DMSO (5ml), this solution of added to a heated solution of DMSO (15 ml) at 130°C. The temperature of the mixture is then slowly raised to 160°C and stirred at this temperature for 15 minutes. After cooling down the solution, a small amount of a saturated aqueous solution of Na2CO3 is added. Extraction of the product with diethyl ether. Crude compound used without further purification. 1H NMR (400 MHz, CDCl3, 298K) delta 10.00 (s, 1H, CHO), 9.22 (d, 3J (H, H) = 1.5 Hz, 1 H, ArH), 8.34 (dd, 3J (H, H) = 6.0 Hz ; 2.0 Hz, 1 H, ArH), 7.90 (d, 3J (H, H) = 8.0 Hz, 1 H, ArH), 3.87 (s, 3 H, CH3).

  • 4
  • [ 110-91-8 ]
  • [ 10165-86-3 ]
  • [ 201852-49-5 ]
  • 6-((E)-1-Morpholin-4-yl-3-phenyl-allyl)-nicotinic acid methyl ester [ No CAS ]
  • 5
  • [ 10165-86-3 ]
  • (1E,2Z)-2-hydrazono-2-phenylacetaldehyde oxime [ No CAS ]
  • [ 913188-65-5 ]
  • 6
  • [ 10165-86-3 ]
  • 4-methyl-α-oximinoacetophenone hydrazone [ No CAS ]
  • [ 913188-66-6 ]
  • 7
  • [ 10165-86-3 ]
  • hydrazono-(4-methoxy-phenyl)-acetaldehyde oxime [ No CAS ]
  • [ 913188-67-7 ]
  • 8
  • [ 56026-36-9 ]
  • [ 10165-86-3 ]
YieldReaction ConditionsOperation in experiment
97% With manganese(IV) oxide; In dichloromethane; at 20℃; for 4h; A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97%).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min).
97% With manganese(IV) oxide; In dichloromethane; at 20℃; for 4h; (c) methyl 6-formylnicotinate A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g, 37 mmol) and MnO2 (32.3 g, 372 mmol) in DCM (200 mL) was stirred at 20 C. for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc=5/1) to afford methyl 6-formylnicotinate (6 g, 97%). MS-ESI (m/z): 166.2 (M+1)+ (LC-MS method C; Ret. time: 0.36 min).
86% With Dess-Martin periodane; In dichloromethane; at 20℃;Inert atmosphere; Dess-Martin periodinane (3.0 g, 7.2 mmol) was added slowly to the mixture of compound 38 (1.0 g,6.0 mmol) in DCM (10 mL). The resulting mixture continued to stir at room temperature overnight.The reaction was quenched with water. The aqueous phase was extracted with EtOAc. The combinedorganic phases were then processed in the usual way and chromatographed (3:1 petroleum ether/EtOAc)to yield compound 39 (0.85 g, 86%).
85.6% With Dess-Martin periodane; In dichloromethane; The A solution of compound 25 (1.0 g, 6. Ommol)Dissolved in dichloromethane (10 mL)in,Add a Dess-Martin periodinane(3.0 g, 7.2 mmo 1)TLC to track the degree of completion of the assay,After the reaction is completed,Water extraction, ethyl acetate extraction,Concentration gave compound 26 (0.6 g, 85.6%
71.4% To a solution of oxalyl chloride (2.0 M in dichloromethane, 8.97 mL) in dichloromethane (35 mL) at -78 C was added (methylsulfinyl)methane (2.55 mL, 35.9 mmol) dropwise. This mixture was allowed to stir at -78 C for 10 minutes then methyl 6-(hydroxymethyl)nicotinate (2.0 g, 11.96 mmol, Combi-Blocks) was added. The mixture was allowed to stir for an additional 15 minutes and triethylamine (6.67 mL, 47.9 mmol) was added, and the mixture was stirred for an additional 15 minutes at -78 C. The dry ice-acetone bath was then replaced with an ice-water bath, and the mixture was allowed to stir for 20 minutes. The mixture was quenched with saturated, aqueous NaHC( (15 mL) and the layers were separated. The aqueous layer was extracted with dichlorome thane (3 x 10 mL), and the combined organic fractions were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via column chromatography (Si(, 50% ethyl acetate/heptanes) to give the title compound (1.41 g, 8.54 mmol, 71.4% yield). MS (ESI+) m/z 166 (M+H)+.
With Dess-Martin periodane; In dichloromethane; for 3h; Dess-Martin reagent (207 mg, 0.49 mmol) was added to a stirring solution of 6- hydroxymethyl-nicotinic acid methyl ester (55 mg, 0.33 mmol) in DCM (17 mL). After stirring for 3 h the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (elution with n-hexane/EA 4:1) to give the title compound.GCMS (m/z): 165.2
With manganese(IV) oxide; In dichloromethane; at 20℃; for 4h; A mixture of methyl 6-( ydroxymethyi)nicotinate (7 g, 37 mmol) and Mn02 (32,3 g,372 mmoi) in DCM ( 200 mL ) was stirred at 20 Q for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel(PE/EtOAc = 5/i) to afford methyl 6-formylnicotinate. MS-ESI (m/z): 166.2 (M+i) + (LC-.MSmethod D; Ret. time: 0.36 mm).
With manganese(IV) oxide; In dichloromethane; at 20℃; Intermediate 11-14 Step 1 : methyl 6-formylnicotinate To a solution of methyl 6-(hydroxymethyl)nicotinate (30 g, 179.6 mmol) in DCM (500 mL) was added MnC>2 (93.8 g, 1077.8 mmol). The mixture was stirred at room temperture overnight. The reaction mixture was filtered and concentrated. The residue was purified by column chromatography on silica gel eluted with PE/EA = 10/1 to give methyl 6-formylnicotinate. XH NMR (400 MHz, CDC13) delta ppm 3.98 (d, J= 0.78 Hz, 3 H), 8.01 (d, J= 8.0 Hz, 1 H), 8.40 - 8.49 (m, 1 H), 9.29 - 9.38 (m, 1 H), 10.11 (s, 1 H).

  • 9
  • [ 10165-86-3 ]
  • [ 107-21-1 ]
  • [ 849662-01-7 ]
YieldReaction ConditionsOperation in experiment
81% toluene-4-sulfonic acid; In toluene; for 7.5h;Heating / reflux; 6-Formyl-nicotinic acid methyl ester (300 mg, 1.82 mmol) was dissolved in toluene (25 ml) and ethylene glycol (0.33 ml, 5.92 mmol) and p-toluenesulfonic acid (cat) were added. The mixture is refluxed with a dean-stark for 7.5 hours. The solvents are evaporated and the crude product was purified by column chromatography (SiO2, CH2Cl2/MeOH =99/1). The protected aldehyde was obtained as a white solid (310 mg, 81 percent). 1H NMR (400 MHz, CDCl3, 298K) delta 9.18 (d, 3J(H, H) = 1.8 Hz, 1H, ArH), 8.31 (dd, 3J(H, H) = 8.2Hz ; 2.2 Hz, 1H, ArH), 7.59 (d, 3J(H, H) = 8.0 Hz, 1H, ArH), 5.87 (s, 1H, CH), 4.16-4.05 (m, 4 H, CH2), 3.93 (s, 3 H, CH2). 13C NMR (100 MHz, CDCI3, 298K) delta 165.5 (C=O), 161.0 (ArC), 150.5 (ArCH), 138.0 (ArCH), 126.2 (ArC), 120.3 (ArCH), 103.1 (CH), 65.7 (CH2), 52.5 (CH3).
  • 10
  • [ 1001200-43-6 ]
  • [ 10165-86-3 ]
  • 11
  • [ 10165-86-3 ]
  • [ 101-77-9 ]
  • [ 849662-06-2 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 3h; 6-Formyl-nicotinic acid methyl ester (30 mg, 0. 18 mmol) and 4,4'-methylene dianiline (17 mg, 0.086 mmol) were dissolved in ethanol (10 ml) and the mixture was stirred for 3 hours. The ligand was obtained by filtration as a white-yellow solid (33 mg, percent). FAB-MS Calcd for C29H24N4O4 m/z= 492.2, Found m/z =493. 1 [M=H]. 1H NMR (400 MHz, CDCl3, 298K) delta 9.28 (d, 1H, 3J(H, H) = 1.5 Hz ArH), 8.67 (s, 1H, CH), 8.39 (d, 3J(H, H) = 8.3 Hz; 2.0 Hz, 1 H, ArH), 8.28 (d, 3J(H, H) = 7.8 Hz, 1 H, ArH), 7.30-7.22 (m, 4H, ArH), 4.05 (s, 1H, CH2), 3.98 (s, 3H, CH3).
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; ;