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[ CAS No. 14161-11-6 ] {[proInfo.proName]}

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Chemical Structure| 14161-11-6
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Product Details of [ 14161-11-6 ]

CAS No. :14161-11-6 MDL No. :MFCD00006464
Formula : C4HCl3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GBAOOJAWDCNOGO-UHFFFAOYSA-N
M.W : 183.42 Pubchem ID :70111
Synonyms :

Calculated chemistry of [ 14161-11-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
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 : 37.06
TPSA : 25.78 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 2.06
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.99
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.313 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 1.08 mg/ml ; 0.00589 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0579 mg/ml ; 0.000316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 14161-11-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14161-11-6 ]

* 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.

  • Upstream synthesis route of [ 14161-11-6 ]
  • Downstream synthetic route of [ 14161-11-6 ]

[ 14161-11-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 14161-11-6 ]
  • [ 20744-39-2 ]
Reference: [1] Patent: US4728355, 1988, A,
[2] Patent: US4735650, 1988, A,
[3] Patent: WO2011/38572, 2011, A1, . Location in patent: Page/Page column 52
  • 2
  • [ 14161-11-6 ]
  • [ 89180-50-7 ]
  • [ 53180-76-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1423 - 1428
[2] Pharmaceutical bulletin, 1956, vol. 4, # 6, p. 497 - 499
[3] Patent: WO2011/38572, 2011, A1, . Location in patent: Page/Page column 52
  • 3
  • [ 14161-11-6 ]
  • [ 7664-41-7 ]
  • [ 89180-50-7 ]
  • [ 53180-76-0 ]
Reference: [1] Pharmaceutical bulletin, 1956, vol. 4, # 6, p. 497 - 499
  • 4
  • [ 14161-11-6 ]
  • [ 53180-76-0 ]
YieldReaction ConditionsOperation in experiment
36% With ammonium hydroxide In ethanol at 120℃; for 0.416667 h; Microwave irradiation A mixture of 3,4,5-trichloropyridazine (Preparation 3, 500 mg, 2.73 mmole) in EtOH (5.5 mL) and NH4OH (5.5 mL) was heated under microwave irradiation 120° C. for 25 minutes. Concentration under reduced pressure and purification via silica gel column chromatography eluting with acetone:dichloromethane (0-15percent acetone), provided the title product in 36percent yield, 163 mg. 1H NMR (400 MHz, CDCl3): δ ppm 5.11 (br s, 2H), 8.74 (s, 1H). LCMS Rt=0.27 minutes MS m/z 164 [M+H]+
36% With ammonium hydroxide In ethanol at 120℃; for 0.416667 h; Microwave irradiation Preparation 21 3,5-Dichloropyridazin-4-amine A mixture of 3,4,5-trichloropyridazine (Preparation 22, 500 mg, 2.73 mmole) in EtOH (5.5 mL) and NH4OH (5.5 mL) was heated under microwave irradiation 120°C for 25 minutes. The reaction was concentrated in vacuo and purified using silica gel column chromatography eluting with acetone:dichloromethane (0-15percent acetone) to afford the title compound (163 mg, 36percent). 1 H NMR (400 MHz, CDCI3): δ ppm 5.1 1 (br s, 2H), 8.74 (s, 1 H). MS m/z 164 [M35CI35CI+H]+
Reference: [1] Patent: US2014/171435, 2014, A1, . Location in patent: Paragraph 0454; 0455; 0456
[2] Patent: WO2015/189744, 2015, A1, . Location in patent: Page/Page column 66
[3] Patent: WO2015/198045, 2015, A1, . Location in patent: Page/Page column 97
  • 5
  • [ 14161-11-6 ]
  • [ 89180-50-7 ]
  • [ 53180-76-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1423 - 1428
[2] Pharmaceutical bulletin, 1956, vol. 4, # 6, p. 497 - 499
[3] Patent: WO2011/38572, 2011, A1, . Location in patent: Page/Page column 52
  • 6
  • [ 14161-11-6 ]
  • [ 7664-41-7 ]
  • [ 89180-50-7 ]
  • [ 53180-76-0 ]
Reference: [1] Pharmaceutical bulletin, 1956, vol. 4, # 6, p. 497 - 499
  • 7
  • [ 932-22-9 ]
  • [ 14161-11-6 ]
YieldReaction ConditionsOperation in experiment
94% at 120℃; for 24 h; A mixture of 4,5-dichloro-3-hydroxypyridazine (25 g, 151 mmol) in phosphorus oxychloride (80 mL) was stirred at reflux (120°C) for 24 h. POCI3 was removed under reduced pressure and the residue was placed into a -78°C bath. After 5-10 min, ice (300 mL) was added, the -78°C bath was exchanged by a 0°C bath, and the mixture was allowed to warm slowly to rt. Once the ice was melted, the white cake deposited was crushed and the mixture was stirred overnight. Solids were filtered off, washed with water, and dried to give Intermediate I-09 (26.105 g, 94percent) as a white solid.HPLC-MS (method 4): Rt= 3.3 min, [M+H]+ m/z 183.
90% at 110℃; for 18 h; 4,5-dichloropyridazin-3(2H)-one (10.0 g, 60.6 mmole) in POCl3 (60 mL, 642 mmole) was stirred at 110° C. for 18 hours. Toluene was added and the solvents removed under reduced pressure. EtOAc (200 mL) and water were added to the resulting residue and the organic layer washed with water and brine and then dried over MgSO4. Concentration under reduced pressure provided the desired product as an off whie solid in 90percent yield, 10 g. 1H NMR (400 MHz, CDCl3): δ ppm 9.10 (d, 1H).
90% at 110℃; for 18 h; Preparation 22 3,4,5-Trichloropyridazine 4,5-Dichloropyridazin-3(2/-/)-one (10. Og, 60.6 mmole) in POCI3 (60 mL, 642 mmole) was stirred at 110°C for 18 hours. The reaction was concentrated in vacuo azeotroping with toluene. EtOAc (200 mL) and water were added to the resulting residue and the organic layer was washed with water and brine, dried over MgS04 and concentrated in vacuo to afford the title compound as an off white solid (10 g, 90percent). 1 H NMR (400 MHz, CDCI3): δ ppm 9.10 (d, 1 H).
89% for 5 h; Heating / reflux 200 g of commercially available 4,5-dichloro-3(2H)-pyridazinone are refluxed in 1500 cm3 of phosphorus oxychloride for 5 hours. Then the excess of phosphorus oxychloride is distilled off in vacuo. The residue is poured onto icy water, the crystalline product is filtered and dried. Yield: 200 g (89percent) of 3,4,5-trichloro-pyridazine. M.p.: 58-60° C.
89% for 2 h; Inert atmosphere; Reflux Example 372: 5-[(3R)-3-(Methylamino)pyrrolidin-1-yl]-N-(2- phenylethyl)pyhdazin-3-amine. --> 3,4,5-trichloropyridazine. A solution of 4,5-dichloropyridazin-3(2H)-one (2 g, 12 mmol) in 20 ml_ of phosphoryl trichloride was heated to reflux for 2 hrs. The solvent was removed under reduce pressure. The residue was poured into water with stirring and extracted with dicloromathene (50 ml_*3). The organic layer was washed with brine, dried over Na2SO4, evaporated to give the crude product. The crude product was recrystallized with acetone/water to give the product (2 g, 89percent). 1H NMR (300 MHz, CDCI3): 9.09 (s, 1 H); LC- MS: m/z = 182.9 [M+H]+. (R)-tert-butyl 1-(5,6-dichloropyhdazin-4-yl)pyrrolidin-3-ylcarbamate. To a stirred solution of 3,4,5-trichloropyridazine (500 mg, 2.7mmol) and DIPEA (1 ml_) in propan-2-ol (5 ml_) was added (R)-tert-butyl pyrrolidin-3- ylcarbamate (508mg, 2.7 mmol) at ambient temperature (18 h). The solvent was removed and the residue was purified by column chromatography (Petroleum Ether/Ethyl Acetate =2/1 , v/v) to afford the title desired product (500mg, 55percent). 1H NMR (300 MHz, CDCI3): 8.42 (s, 1 H), 5.06 (br s, 1 H), 4.36 (br s, 1 H), 4.05-3.99 (m, 1 H), 3.90-3.66 (m, 3H), 2.28-2.23 (m, 1 H), 2.09-2.07 (m, 1 H), 1 .48 (s, 9H); LC-MS: m/z = 333.1 [M+H]+ (R)-tert-butyl 1 -(5,6-dichloropyridazin-4-yl)pyrrolidin-3-yl(methyl)- carbamate. NaH (60percent in oil, 0.72 g, 18.0 mmol) was suspended in 40 mL of anhydrous DMF. A solution of (R)-tert-butyl 1-(5,6-dichloropyridazin-4-yl)pyrrolidin-3- ylcarbamate (5g, 15mmol) in anhydrous DMF (40 mL) was added at -5 0C. After 40 min, CH3I (2.55 g, 18 mmol) was added. Then the resulting mixture was stirred at ambient temperature for 2 hours. The reaction was monitored by LC-MS. Water (100 mL) was added and the mixture was extracted with EtOAc (3 x 200 mL). The organic layer was washed with brine (3 x 200 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel (Petroleum Ether/ EtOAc = 5 / 1 , v/v) to afford the desired product (4.2 g, 80percent). 1H NMR (300 MHz, CDCI3) δ 8.39 (s, 1 H), 4.77-4.76 (m, -->1 H), 3.86-3.62 (m, 4H), 2.85 (s, 3H), 2.18-2.1 1 (m, 2H), 1.46 (s, 9H); LC-MS: m/z - 347.1 [M+H]+. (f?)-tert-butyl1-(5-chloro-6-(phenethylarnino)pyridazin-4-yl)pyrrolidin-3- yl(methyl)- carbamate. A mixture of (R)-tert-butyl 1-(5,6-dichloropyridazin-4- yl)pyrrolidin-3-yl(methyl) carbamate (400 mg, 1.15mmol) and 2- phenylethanamine (1 mL) was stirred at 1500C for 40 min in microwave. The mixture was concentrated and the residue was purified by silica gel chromatography (MeOH/DCM=1/50, v/v) to afford the desired product (295 mg, 59percent). LC-MS: m/z = 432.1 [M+H]+. (f?)-tert-butylmethyl(1 -(6-(phenethylamino)pyhdazin-4-yl)pyrrolidin-3- yl) carbamate. To a mixture of (f?)-tert-butyl1 -(5-chloro-6- (phenethylamino)pyhdazin-4-yl)pyrrolidin-3-yl(methyl)- carbamate (295mg, 0.68mmol) and HCOONH4 (0.5 g, 7.9 mmol) in MeOH (15 mL) was added 10percent Pd/C (0.3 g) and the resulting mixture was refluxed 30 min. The reaction was allowed to cool and filtered. The filtrate was concentrated, then diluted with EA (2OmL) and washed with brine (10mL*2). The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by prep-HPLC to give the product as oil (177mg, 65percent). 1H NMR (300 MHz, CDCI3): δ 8.80 (s, 1 H), 7.70 (d, J = 5.4 Hz 1 H), 7.30-7.18 (m, 5H), 5.30 (5.30, J = 9.6 Hz, 1 H), 4.86 (d, J = 6.3Hz, 1 H), 3.78-3.73 (m, 1 H), 3.49-3.35 (m, 4H), 2.96 (t, J = 7.2 Hz, 2H), 2.82 (s, 3H), 2.23 (s,2H), 1.48 (s, 9H); LC-MS: m/z = 398.1 [M+H]+. (f?)-5-(3-(methylamino)pyrrolidin-1-yl)-N-phenethylpyridazin-3-amine dihydrochloride. To a solution of (f?)-tert-butylmethyl(1-(6- (phenethylamino)pyhdazin-4-yl) pyrrolidin-3-yl)carbamate (177mg, 44mmol) in MeOH (3mL) was added ether solution of HCI gas (7N, 1 OmL). The reaction was stirred at room temperature for 16 hours. The solution was concentrated under reduced pressure to give the desired product as a white solid (32.2mg, 20percent). 1H NMR (300 MHz, CD3OD): 8.13 (d, J =2.4 Hz, 1 H), 7.33-7.25 (m, 5H), 5.98 (d, J = 2.4 Hz, 1 H), 4.01-3.62 (m, 7H), 3.00 (t, J = 6.9 Hz, 2H), 2.84 (s, 3H), 2.60-2.30 (m, 2H); LC-MS: m/z = 298.3 [M+H]+, tR = 1 .0 min; HPLC: 98percent (214 nm), 99percent (254 nm), tR = 7.1 min.

Reference: [1] Patent: WO2013/4984, 2013, A1, . Location in patent: Page/Page column 70
[2] Patent: US2014/171435, 2014, A1, . Location in patent: Paragraph 0451; 0452; 0453
[3] Patent: WO2015/189744, 2015, A1, . Location in patent: Page/Page column 66-67
[4] Patent: US6800758, 2004, B1, . Location in patent: Page column 12
[5] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10311 - 10322
[6] Patent: WO2009/152325, 2009, A1, . Location in patent: Page/Page column 193-195
[7] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 5, p. 1301 - 1306
[8] Russian Journal of Applied Chemistry, 2004, vol. 77, # 12, p. 1997 - 2000
[9] Pharmaceutical bulletin, 1956, vol. 4, # 6, p. 497 - 499
[10] Patent: US2002/165241, 2002, A1,
[11] Patent: US4728355, 1988, A,
  • 8
  • [ 932-22-9 ]
  • [ 14161-11-6 ]
Reference: [1] Patent: WO2016/180833, 2016, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2018/82964, 2018, A1, . Location in patent: Page/Page column 31
  • 9
  • [ 186581-53-3 ]
  • [ 6262-42-6 ]
  • [ 14161-11-6 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 2.1, p. 242 - 246[2] Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 2, p. 289 - 294
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