Home Cart 0 Sign in  

[ CAS No. 20511-15-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 20511-15-3
Chemical Structure| 20511-15-3
Structure of 20511-15-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 20511-15-3 ]

Related Doc. of [ 20511-15-3 ]

Alternatived Products of [ 20511-15-3 ]

Product Details of [ 20511-15-3 ]

CAS No. :20511-15-3 MDL No. :MFCD00235124
Formula : C5H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GTLFLMZOABSJSV-UHFFFAOYSA-N
M.W :128.56 Pubchem ID :581932
Synonyms :

Calculated chemistry of [ 20511-15-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.65
TPSA : 38.91 Ų

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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 0.4
Log Po/w (SILICOS-IT) : 1.37
Consensus Log Po/w : 1.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.59 mg/ml ; 0.0201 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 8.14 mg/ml ; 0.0633 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.735 mg/ml ; 0.00571 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 20511-15-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20511-15-3 ]

* 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.

  • Upstream synthesis route of [ 20511-15-3 ]
  • Downstream synthetic route of [ 20511-15-3 ]

[ 20511-15-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 20511-15-3 ]
  • [ 19798-77-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 2
  • [ 13091-23-1 ]
  • [ 20511-15-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Journal of the American Chemical Society, 2015, vol. 137, # 24, p. 7552 - 7555
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 4, p. 519 - 525
  • 3
  • [ 39910-67-3 ]
  • [ 504-24-5 ]
  • [ 20511-15-3 ]
Reference: [1] Heterocycles, 1982, vol. 19, # 6, p. 1043 - 1046
  • 4
  • [ 20511-15-3 ]
  • [ 22889-78-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 5
  • [ 20511-15-3 ]
  • [ 89284-61-7 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 0.5 h;
Stage #2: With sodium cyanide In water; acetonitrile at 0 - 20℃; for 10 h;
[Example 719] Compound q1 4-Chloropyridine-3-carbonitrile [1519] aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0°C. An aqueous solution (10 ml) of sodium nitrite (725 mg, 10.5 mmol) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0°C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0°C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44percent) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) δ: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).
Reference: [1] Patent: EP2842939, 2015, A1, . Location in patent: Paragraph 1519; 1520
  • 6
  • [ 20511-15-3 ]
  • [ 773837-37-9 ]
  • [ 89284-61-7 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 0.5 h;
Stage #2: at 0 - 25℃; for 10 h;
A 48percent aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0°C. A solution of sodium nitrite (725 mg, 10.5 mmol) in water (10 ml) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0°C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0°C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44percent) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) δ: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).
Reference: [1] Patent: EP2842946, 2015, A1, . Location in patent: Paragraph 1536; 1537
  • 7
  • [ 617-35-6 ]
  • [ 20511-15-3 ]
  • [ 24334-19-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 39, p. 11859 - 11862[2] Angew. Chem., 2016, vol. 128, p. 12038 - 12041,4
  • 8
  • [ 20511-15-3 ]
  • [ 24334-19-8 ]
Reference: [1] Synthesis, 2005, # 15, p. 2571 - 2577
  • 9
  • [ 20511-15-3 ]
  • [ 140-89-6 ]
  • [ 65128-66-7 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 95 - 100℃; for 15 h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide for 0.5 h;
Thiazolo[4,5-c]pyridine-2-thiol (68): Compound 67 (1.0 g, 8.3 mmol) was dissolved in 15 mL of dry DMF under N2. KSCSOEt (2.0 g, 12.5 mmol) was added EPO <DP n="147"/>to the solution as a solid. The reaction mixture was stirred at 95-1000C for 15h. TLC (70percent EtO Ac/Hex) showed consumption of starting material. The reaction was quenched with -35 mL OfH2O followed by addition of 40 mL of IM HCl. The mixture was stirred for 30 min, during which time precipitate was obtained. The precipitate was filtered, washed with 250 mL of H2O and dried under vacuum over P4Oi0 to yield compound 68 (0.98Og, 70percent).
Reference: [1] Patent: WO2006/122156, 2006, A2, . Location in patent: Page/Page column 145-146
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
  • 10
  • [ 20511-15-3 ]
  • [ 98-80-6 ]
  • [ 146140-99-0 ]
YieldReaction ConditionsOperation in experiment
< 100 %Chromat. With potassium carbonate In water at 100℃; for 3 h; The following were charged into a 1000 ml reactor provided with a coolant, a magnetic stirrer, a thermocouple and a nitrogen atmosphere: [00164] 38.56 g (300 mmole) of 4-chloro-3-aminopyridine; [00165] 42.2 g (306 mmole) of 100percent potassium carbonate; [00166] 38.4 g (308 mmole) of 97percent phenylboronic acid; [00167] 20 mg (0.112 mmole) of palladium chloride; [00168] 400 g (22.2 mole) of degassed water. [00169] The reactants were charged into the reactor and heated under reflux (100° C.) with stirring and under nitrogen. [00170] The reaction was complete after 3 h. [00171] Extraction was carried out with isopropyl ether (200 ml). [00172] It was quickly decanted. [00173] The organic phase was washed with 2.x.60 ml of water. [00174] It was dried over magnesium sulphate then concentrated by evaporation. [00175] High performance liquid chromatography analysis measured 51 g of 4-phenyl-3-methylaniline, corresponding to a yield of close to 100percent.
Reference: [1] Patent: US6800784, 2004, B1, . Location in patent: Page column 9-10
  • 11
  • [ 20511-15-3 ]
  • [ 1093211-85-8 ]
  • [ 1885-14-9 ]
  • [ 1346528-50-4 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With pyridine In toluene at 2 - 5℃; for 7.5 h; Inert atmosphere
Stage #2: at 6 - 20℃; for 15 h;
A 2 L, three-neck Morton flask equipped with a mechanical stirrer, thermocouple, and addition funnel under a nitrogen atmosphere was charged with 3-amino-4-chloropyridine (35.0 g, 272 mmol) and toluene (740 mL). The brown solution was cooled to 2 °C. Pyridine (25.3 mL, 310 mmol) was added in one portion, followed by the dropwise addition of phenyl chloroformate (32.6 mL, 259 mmol) over 30 min. The maximum internal temperature was 5 °C. After stirring at 2-5 °C for 7 h the reaction mixture became a thick yellow suspension. A cooled solution of K2CO3 (53.6 g, 388 mmol) in water (216 mL) was added over 3 min, during which the maximum internal temperature was 6 °C. 1 -(2,2-Difluoro-benzo[1 ,3]dioxol-5-ylmethyl)-piperazine (66.3 g, 259 mmol) was then added as a solid over 1 min. The mixture was allowed to warm slowly to room temperature and stirred for 15 h. Water (200 ml_) was added and the toluene layer was separated and extracted with aqueous HCI (1 .8 M, 600 ml_). The aqueous extract was washed with toluene (2 x 300 ml_). MeOH (500 ml_) was added to the aqueous layer and the solution was cooled to 5 °C. The pH was adjusted to pH 8-9 with the addition of NaOH solution (50 wtpercent, ca. 50 ml_). The addition was at such a rate that the internal temperature did not exceed 17 °C. The resulting suspension was stirred at 5 °C for 2 h. The product was collected by filtration and rinsed with MeOH/H2O (1 :1 , 70 ml_). The solid was dried in vacuum oven at 50 °C for 24 h to afford the title compound as a yellow/green solid (73 g, 69percent).A 1 L, three-neck Morton flask equipped with a stir bar, thermocouple, and reflux condenser was charged with crude 4-(2,2-difluoro-benzo[1 ,3]dioxol- 5-ylmethyl)-piperazine-1 -carboxylic acid (4-chloro-pyridin-3-yl)-amide (98 g, 239 mmol) and isopropyl acetate (318 ml_). The suspension was heated to 65 °C, treated with activated charcoal (10.0 g) and stirred at 65 °C for 1 h. The mixture was then heated to 80 °C and quickly filtered through a thin celite pad. The filtrate was slowly cooled to room temperature and then placed in an ice bath for 30 min. The solid was collected by filtration, rinsed with cold iPrOAc (10 ml_), and dried to give product 4-(2,2-difluoro-benzo[1 ,3]dioxol-5-ylmethyl)- piperazine-1 -carboxylic acid (4-chloro-pyridin-3-yl)-amide as a yellow solid (72 g, 73percent).A 2 L, three-neck Morton flask equipped with a mechanical stirrer, thermocouple, and reflux condenser was charged with crude product 4-(2,2- difluoro-benzo[1 ,3]dioxol-5-ylmethyl)-piperazine-1 -carboxylic acid (4-chloro- pyridin-3-yl)-amide (191 g, 465 mmol) and isopropyl acetate (705 ml_). The suspension was heated to 65 °C, treated with activated charcoal (1 1 .2 g) and stirred at 65 °C for 1 h. The mixture was then heated to 75 °C and quickly filtered. The filtrate was slowly cooled to room temperature overnight and then placed in an ice bath for 30 min. The solid was collected by filtration, rinsed with cold iPrOAc (40 ml_), and dried in vacuum oven at 50 °C for 72 h. The product 4-(2,2-difluoro-benzo[1 ,3]dioxol-5-ylmethyl)-piperazine-1 -carboxylic acid (4-chloro-pyridin-3-yl)-amide was obtained as a slightly yellow solid (161 g, 84percent). MS (ESI+): calcd for Ci8Hi7CIF2N4O3 m/z 410.1 , found 41 1 .1 (M+H)+. Anal. Calcd for Ci8H17CIF2N4O3: C, 52.63; H, 4.17; N, 13.64. Found: C, 52.73; H, 4.15; N, 13.62; 1 H NMR (600 MHz, CDCI3) δ: 9.36 (s, 1 H), 8.19 (d, J = 5.2 Hz, 1 H), 7.29 (dd, J = 5.3, 0.3 Hz, 1 H), 7.13 (d, J = 0.9 Hz, 1 H), 7.02-6.98 (m, 5 2H), 6.84 (s, 1 H), 3.58-3.54 (m, 4H), 3.53 (s, 2H), 2.54-2.48 (m, 4H); 13C NMR (151 MHz, CDCIs) δ: 153.49, 144.02, 143.88, 143.28, 142.98, 134.05, 133.09, 131 .66 (t, JC-F = 254.6 Hz), 131 .55, 123.89, 123.53, 1 10.03, 109.02, 62.28, 52.47, 44.23.
Reference: [1] Patent: WO2011/139951, 2011, A1, . Location in patent: Page/Page column 24-26
  • 12
  • [ 20511-15-3 ]
  • [ 1352792-74-5 ]
Reference: [1] Patent: CN106883169, 2017, A,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 20511-15-3 ]

Chlorides

Chemical Structure| 89284-39-9

[ 89284-39-9 ]

4,5-Dichloropyridin-3-amine

Similarity: 0.91

Chemical Structure| 22353-34-0

[ 22353-34-0 ]

5-Chloropyridin-3-amine

Similarity: 0.86

Chemical Structure| 7321-93-9

[ 7321-93-9 ]

4,6-Dichloropyridin-3-amine

Similarity: 0.84

Chemical Structure| 173772-63-9

[ 173772-63-9 ]

3-Amino-2,4-dichloropyridine

Similarity: 0.81

Chemical Structure| 24484-98-8

[ 24484-98-8 ]

4-Chloropyridine-2,3-diamine

Similarity: 0.81

Amines

Chemical Structure| 89284-39-9

[ 89284-39-9 ]

4,5-Dichloropyridin-3-amine

Similarity: 0.91

Chemical Structure| 22353-34-0

[ 22353-34-0 ]

5-Chloropyridin-3-amine

Similarity: 0.86

Chemical Structure| 7321-93-9

[ 7321-93-9 ]

4,6-Dichloropyridin-3-amine

Similarity: 0.84

Chemical Structure| 173772-63-9

[ 173772-63-9 ]

3-Amino-2,4-dichloropyridine

Similarity: 0.81

Chemical Structure| 24484-98-8

[ 24484-98-8 ]

4-Chloropyridine-2,3-diamine

Similarity: 0.81

Related Parent Nucleus of
[ 20511-15-3 ]

Pyridines

Chemical Structure| 89284-39-9

[ 89284-39-9 ]

4,5-Dichloropyridin-3-amine

Similarity: 0.91

Chemical Structure| 22353-34-0

[ 22353-34-0 ]

5-Chloropyridin-3-amine

Similarity: 0.86

Chemical Structure| 7321-93-9

[ 7321-93-9 ]

4,6-Dichloropyridin-3-amine

Similarity: 0.84

Chemical Structure| 173772-63-9

[ 173772-63-9 ]

3-Amino-2,4-dichloropyridine

Similarity: 0.81

Chemical Structure| 24484-98-8

[ 24484-98-8 ]

4-Chloropyridine-2,3-diamine

Similarity: 0.81