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[ CAS No. 1480-65-5 ] {[proInfo.proName]}

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Chemical Structure| 1480-65-5
Chemical Structure| 1480-65-5
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Product Details of [ 1480-65-5 ]

CAS No. :1480-65-5 MDL No. :MFCD04112513
Formula : C5H3ClFN Boiling Point : -
Linear Structure Formula :- InChI Key :ZULRQGBHWBQPFE-UHFFFAOYSA-N
M.W : 131.54 Pubchem ID :345817
Synonyms :

Calculated chemistry of [ 1480-65-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.2
TPSA : 12.89 ?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) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 1.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.538 mg/ml ; 0.00409 mol/l
Class : Soluble
Log S (Ali) : -1.76
Solubility : 2.27 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.88
Solubility : 0.172 mg/ml ; 0.00131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 1480-65-5 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P261-P280-P305+P351+P338 UN#:2924
Hazard Statements:H225-H302-H315-H318-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1480-65-5 ]

* 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 [ 1480-65-5 ]

[ 1480-65-5 ] Synthesis Path-Downstream   1~13

YieldReaction ConditionsOperation in experiment
By following the above procedures, and employing the appropriate starting pyridine compounds, the following compounds are prepared:2,5-Difluoropyridine; 2,5-dibromopyridine; 2-chloro-5-bromopyridine; 2-chloro-5-fluoropyridine; 2-fluoro-5-chloropyridine; 2-bromo-5-chloropyridine; and 2-bromo-5-fluoropyridine.
Representative halopyridine compounds which can be prepared by the method of the present invention include:...2,5-difluoropyridine; 2,5-dibromopyridine; 2-chloro-5-bromopyridine; 2-chloro-5-fluoropyridine; 2-fluoro-5-chloropyridine; 2-fluoro-5-bromopyridine; 2-bromo-5-chloropyridine; 2-bromo-5-fluoropyridine; ...
  • 2
  • (5R)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diaza-spiro[4.5]decan-1-one hydrochloride [ No CAS ]
  • [ 1480-65-5 ]
  • (5R)-7-(5-chloropyridin-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diaza-spiro[4.5]decan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h; Example 116 EPO <DP n="90"/>(5R)-7-(5-ChIoropyridin-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diazaspiro[4.5]decan-l-one A mixture of (5R)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diazaspiro[4.5]decan-l-one hydrochloride (29.4 mg, 0.000107 mol, this compound was prepared by using procedures analogous to those described for the synthesis of example 1, steps 1-5), <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (17 mg, 0.00013 mol) and potassium carbonate (0.029 mL, 0.00032 mol) in N,N-dimethylformamide (0.6 mL, 0.008 mol) was heated at 120 0C for 5 h. The crude product was purified by prep-HPLC to afford the desired product. LC-MS: 350.2 (M+H)+.
  • 3
  • [ 1480-65-5 ]
  • [ 659731-48-3 ]
YieldReaction ConditionsOperation in experiment
Step A 5-Chloro-2-fluoro-4-iodopyridine (4-2); <strong>[1480-65-5]5-Chloro-2-fluoropyridin</strong>e (4-1, 1Og, 76.0 mmol) was adde dropwise at -78 0C to the solution of LDA (2.1M, 400 mL). The reaction mixture was stirred at the same temperature for 7 h, treated with solid I2, (19.3 g, 76.0 mmol) stirred for 2 h, quenched with water, and partitioned between hexanes and water. The organic layer was washed with IN-HCl and then with brine, separated, dried (MgSO4) and concentrated in vacuo to give the crude product. Chromatography (SiO2, hexanes only) afforded the desired isomer (4-2) as a minor product.
  • 4
  • [ 1480-65-5 ]
  • [ 1040745-70-7 ]
  • [ 1041642-20-9 ]
  • 5
  • [ 1480-65-5 ]
  • potassium 1-trifluoroborato-5-phenylpentan-3-one [ No CAS ]
  • [ 1112788-71-2 ]
  • 6
  • potassium (4-(benzoyloxy)butyl)trifluoroborate [ No CAS ]
  • [ 1480-65-5 ]
  • [ 1137726-28-3 ]
  • 7
  • [ 1480-65-5 ]
  • potassium 3-trifluoroboratopropionic acid N,N-dimethyl amide [ No CAS ]
  • [ 1174066-62-6 ]
  • 8
  • [ 71-23-8 ]
  • [ 1480-65-5 ]
  • [ 1160018-61-0 ]
YieldReaction ConditionsOperation in experiment
98% A 12 L three-neck round-bottom flask with a mechanical stirrer, thermocouple, addition funnel, nitrogen inlet, and a drying tube were equipped and placed into a cooling bath. An oversized flask was used due to the large amount of foaming and effervescence during the additions. The flask was charged with tetrahydrofuran (THF, 1.8 L), and stirring was initiated. Sodium hydride was added in portions. A mild exotherm was observed initially due to residual moisture in the solvent. After this had subsided the bulk of the material was added. The reaction mixture was cooled to 0-5° C. using an ice/water bath, and a solution of propanol (103 mL) in THF (350 mL) was added slowly over a 1 hour period at a rate to keep the internal temperature below 5° C. The addition was strongly exothermic and accompanied by the evolution of hydrogen gas. There was a significant delay (45 mins) to the hydrogen release, which was sudden and caused foaming. After the complete addition of propanol, the reaction was stirred for a further 1 h. A solution of <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (22, 86 g) in tetrahydrofuran (THF, 350 mL) was added slowly over a 1.5 hour period at a rate to keep the internal temperature below 5° C. The addition was strongly exothermic and accompanied by the evolution of hydrogen gas. There was a significant delay (45 mins) to the hydrogen release, which was sudden and caused foaming. The cooling bath was allowed to expire naturally overnight. Stirring was continued at ambient temperature until the reaction was complete, i.e., typically after overnight stirring without the requirement for additional reagents and when no starting material was observed. If reaction was not complete, it was cooled back to 0-5° C. and treated with fresh sodium hydride (0.5 eq.), the reaction was stirred at ambient temperature overnight, resampled, and the reaction was continued until deemed to be complete. The reaction was monitored by TLC (SiO2, 25percent ethyl acetate in heptanes, UV) by diluting an aliquot of reaction mixture (1 mL) with water (2 mL), extracting with ethyl acetate, and spotting the organic layer. The starting material had retention factor (RF)=0.38; the product had RF=0.45. Materials used in the synthesis are detailed in Table 3. To isolate 5-chloro-2-propoxypyridine (23), the reaction mixture was cooled to 0-5° C. using an ice/water bath. The reaction was quenched by the addition of a slow stream of saturated aqueous ammonium chloride solution (1 L). The addition was exothermic and may be accompanied by hydrogen gas evolution. The mixture was extracted with ethyl acetate (2.x.2 mL). The combined organic extracts were washed with saturated brine solution (1 L), dried over magnesium sulfate and charcoal, and filtered through a glass fiber filter. The filtrate was concentrated under reduced pressure to give a pale yellow liquid.The reaction was successfully carried out on multi-gram scale giving both excellent yield and purity, and the results are shown in Table 4. 5-Chloro-2-propoxypyridine (23) (lot No. 1357-96-1) was a pale yellow liquid, synthesized with a yield of 110 g/98percent. 5-Chloro-2-propoxypyridine (23) was analyzed using HPLC, and according to results, it was 99.0percent pure. 1H-NMR (300 MHz, CDCl3) was also used to analyze 5-chloro-2-propoxypyridine (23), confirming the identity of the compound.
  • 9
  • [ 1480-65-5 ]
  • [ 1204336-54-8 ]
  • [ 1204336-04-8 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 70 - 100℃; for 88h; To a solution of N-(2-hydroxy-l-hydroxymethylethyl)-2-methyl-6-(3-prperidin-4-yl- propoxy)nicotmamide hydrochloride (Preparation 50, 125 mg, 320 mumol) in DMSO (5 mL) was added <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (70.2 mg, 533 mumol) and DBU (133 muL, 889 mumol) and the resulting solution was stirred at 1000C for 16 h. Further 5-chloro-2-fluoropyndine (93.7 mg,712 mumol) was added to the reaction mixture and heating at 7O0C was continued for 72 h The reaction mixture was diluted with EtOAc, then washed with H2O and brme, before being dried (MgSO4), filtered and concentrated in vacuo to afford the title compound: RT = 2.90 mm; mlz (ES+) = 463 22 [M + U]+ (Method A).
  • 10
  • [ 1480-65-5 ]
  • [ 1204310-22-4 ]
  • [ 1204310-23-5 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene;water; In dimethyl sulfoxide; at 130℃; for 3h;Microwave irradiation; To 2-methyl-4-(3-pipendin-4-ylpropoxy)benzoic acid hydrochloride (Preparation 22, 574 mg, 1.83 mmol) in DMSO (850 muL) was added 5-chloro-2-fluoropyndine (288 mg, 2.20 mmol), DBU (960 muL, 6 41 mmol) and H2O (6 drops) The resulting suspension was heated in a sealed tube in the microwave at 13O0C for 3 h The reaction mixture was diluted with H2O, acidified to pH 5 with 2M HCl and extracted with EtOAc (3x), then the combined organic extracts were washed with brine, before being dried (MgSO4). Filtration, removal of solvent under reduced pressure and purification by column chromatography (EtOAc-IH, 2 3 to 3:2) afforded the title compound: RT = 3.87 min; mlz (ES+) = 403.11 [M + H]+ (Method A).
With 1,8-diazabicyclo[5.4.0]undec-7-ene;water; In dimethyl sulfoxide; at 130℃; for 3h;Microwave irradiation; To 2-methyl-4-(3-piperidin-4-ylpropoxy)benzoic acid hydrochloride (Preparation 21, 574 mg, 1.83 mmol) in DMSO (850 muL) was added <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (288 mg, 2.20 mmol), DBU (960 muL, 6.41 mmol) and H2O (6 drops). The resulting suspension was heated in a sealed tube in the microwave at 13O0C for 3 h. The reaction mixture was diluted with H2O, acidified to pH 5 with 2M HCl and extracted with EtOAc (3x), then the combined organic extracts were washed with brine, before being dried (MgSO4). Filtration, removal of solvent under reduced pressure and purification by column chromatography (EtOAc-IH, 2:3 to 3:2) afforded the title compound: RT = 3.87 min; mlz (ES+) = 403.11 [M + H]+ (Method A).
  • 11
  • [ 1480-65-5 ]
  • 3-(piperidin-4-yl)propan-1-ol hydrochloride [ No CAS ]
  • [ 1204310-31-5 ]
YieldReaction ConditionsOperation in experiment
A stirred solution of 3-piperidin-4-ylpropan-l-ol hydrochloride (15.0 g, 84 mmol) in DMSO (120 mL) was cooled to O0C, before being treated dropwise with DBU (30.0 mL, 201 mmol) over 5 min. 2,5-dichloropyrimidine (17.4 g, 117 mmol) was added portionwise, then the reaction was heated to 11O0C for 4 h. After cooling to 2O0C, the reaction was poured into H2O (200 mL) and extracted with EtOAc (3 x 500 mL). The combined organic extracts were washed with IM HCl (2 x 200 mL), before being dried (MgSO4) and concentrated. The residue was purified by column chromatography (EtOAc-IH, 4:6) to provide the title compound: 1H NMR (CDCl3) delta 1.10-1.23 (m, 2H), 1.30-1.38 (m, 2H), 1.48-1.57 (m, IH), 1.58-1.66 (m, 2H), 1.78 (d, 2H), 2.86 (m, 2H), 3.66 (t, 2H), 4.67 (d, 2H), 8.20 (s, 2H).
  • 12
  • [ 1480-65-5 ]
  • [ 1227471-85-3 ]
  • [ 1227471-97-7 ]
YieldReaction ConditionsOperation in experiment
96.4% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; tert-butyl (3R)-3-(3-[(5-chloropyridin-2-yl)oxylphenyl)-1-oxa-8-azaspiro[4.5ldecane-8-carboxylate To a mixture of tert-butyl (3R)-3-(3-hydroxyphenyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (2.82 g, 8.47 mmol) and cesium carbonate (5.52 g, 16.9 mmol) in DMF (5 ml_) was added <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (1.5 ml_, 15 mmol) and stirred at RT over several nights. Water (50 ml_) and ethyl acetate (150 ml_) were added and the layers were separated. The organic was washed with saturated ammonium chloride (3x50 ml_), dried over magnesium sulfate, filtered, and concentrated to give ~5 g of the crude oil. The oil was purified by flash chromatography (5-30percent EA/Heptane) to give the title compound as a gum (3.80 g, 96.4percent). m/z 389 (MH+ minus t-Bu). 1H NMR (400 MHz, CDCI3) delta ppm 1.47 (s, 9 H), 1.53 - 1.59 (m, 1 H), 1.65 - 1.77 (m, 3 H), 1.82 (dd, J=12.63, 10.24 Hz, 1 H), 2.27 (dd, J=12.63, 8.19 Hz, 1 H), 3.30 - 3.41 (m, 2 H), 3.48 - 3.58 (m, 1 H), 3.62 (br. s., 2 H), 3.80 (t, J=8.88 Hz, 1 H), 4.23 (t, J=8.02 Hz, 1 H), 6.89 (d, J=8.88 Hz, 1 H), 6.96 - 7.02 (m, 2 H), 7.10 (d, J=7.85 Hz, 1 H), 7.35 (t, J=7.68 Hz, 1 H), 7.66 (dd, J=8.53, 2.73 Hz, 1 H), 8.13 (d, J=2.73 Hz, 1 H).
  • 13
  • [ 1480-65-5 ]
  • [ 1011-65-0 ]
  • [ 1252779-91-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 200℃; for 2h;Microwave irradiaition; A mixture of Ij (1.14 mmol, 200 mg), laa (1.14 mmol, 150 mg), K2CO3 (2.28 mmol, 315 mg) and NMP (1.5 mL) was heated at 200 0C in a microwave reactor for 2 h. The mixture was poured into water (50 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under vacuo. Purification was carried by flash column chromatography (silica gel, 15percent EtO Ac/heptane) to give 290 mg of lbb (290 mg).
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