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[ CAS No. 4214-74-8 ] {[proInfo.proName]}

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Product Details of [ 4214-74-8 ]

CAS No. :4214-74-8 MDL No. :MFCD00006313
Formula : C5H4Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :OCWBGKZFOYMCCN-UHFFFAOYSA-N
M.W : 163.01 Pubchem ID :77886
Synonyms :

Calculated chemistry of [ 4214-74-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
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 : 38.66
TPSA : 38.91 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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.8
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.542 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 0.946 mg/ml ; 0.00581 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.89
Solubility : 0.211 mg/ml ; 0.00129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 4214-74-8 ]

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

Application In Synthesis of [ 4214-74-8 ]

* 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 [ 4214-74-8 ]
  • Downstream synthetic route of [ 4214-74-8 ]

[ 4214-74-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 1072-98-6 ]
  • [ 4214-74-8 ]
YieldReaction ConditionsOperation in experiment
70.5% With N-chloro-succinimide In methanol; N,N-dimethyl-formamide at 45℃; for 2.5 h; To a 10 L round bottom three-necked flask was added 5500 ml of a 2.5: 1 mixture of DMF and methanol in a volume ratio of 2.500 ml, inserted into a thermometer and equipped with a condensing reflux device, the magnetic stirrer was started and 2560.8 g of 2-amino- Pyridine, N-chlorosuccinimide 6118.4 g, and the reaction was stirred at 45 ° C for 2.5 hours.TLC and GC were determined to complete the reaction.The crude product was distilled off to give the crude product and recrystallized from ethanol to give pure product 2-amino-3,5-dichloropyridine. After drying, the yield was 70.5percent and the purity was 98.20percent (GC).
Reference: [1] European Journal of Organic Chemistry, 2012, # 28, p. 5595 - 5604
[2] Patent: CN104016908, 2016, B, . Location in patent: Paragraph 0027; 0028
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[4] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
  • 2
  • [ 504-29-0 ]
  • [ 4214-74-8 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 80, p. 14852 - 14855
[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[3] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
[4] Patent: US4033975, 1977, A,
[5] Dyes and Pigments, 2012, vol. 92, # 3, p. 1184 - 1191
  • 3
  • [ 133520-09-9 ]
  • [ 4214-74-8 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 7, p. 834[2] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 7, p. 995
  • 4
  • [ 171774-37-1 ]
  • [ 4214-74-8 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 31, p. 8649 - 8654
  • 5
  • [ 504-29-0 ]
  • [ 1072-98-6 ]
  • [ 4214-74-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531,533
[4] Patent: DE406206, , ,
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[6] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531,533
[8] Patent: DE406206, , ,
[9] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[10] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
[11] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[12] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
[13] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531,533
[14] Patent: DE406206, , ,
[15] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531
[16] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 533
[17] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 533
[18] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531
[19] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 533
[20] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 531
[21] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 533
  • 6
  • [ 16063-70-0 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 7
  • [ 110-86-1 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 8
  • [ 16063-70-0 ]
  • [ 7664-41-7 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 9
  • [ 1072-98-6 ]
  • [ 64-17-5 ]
  • [ 7782-50-5 ]
  • [ 4214-74-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
  • 10
  • [ 5468-71-3 ]
  • [ 7726-95-6 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 11
  • [ 4214-74-8 ]
  • [ 12775-96-1 ]
  • [ 40966-87-8 ]
Reference: [1] Patent: US4033975, 1977, A,
  • 12
  • [ 4214-74-8 ]
  • [ 823-56-3 ]
Reference: [1] Journal of Fluorine Chemistry, 1981, vol. 18, p. 497 - 506
  • 13
  • [ 4214-74-8 ]
  • [ 14482-51-0 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With hydrogen bromide; bromine; sodium nitrite In water at 0 - 70℃; for 1 h;
Stage #2: With potassium hydroxide In water
K: 2-Amino-3,5-dichloropyridine J (10 g, 61.3 mmol) was dissolved in an aqueous HBr solution (100 mL 48percent HBr, 200 niL H2O), then cooled to O0C. Br2 (10 mL) was added in one portion, followed by the dropwise addition OfNaNO2 solution (6.35 g, 92.0 mmol, 15 mL H2O). The mixture was stirred at O0C for 30 minutes, then allowed to warm to room <n="73"/>temperature before being heated to 7O0C for 30 minutes. The cooled mixture was then neutralised with KOH solution (5.0 M) then extracted with ethyl acetate (3 x 200 mL), dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (1:4 EtOAc, hexane) providing 8.2 g (59percent) of K as a yellow crystalline solid. 1H NMR (300 MHz, CDCl3): δ 8.27 (d, J= 2.1 Hz, IH), 7.77 (d, J= 2.1 Hz, IH).
52%
Stage #1: With hydrogen bromide; bromine In water at -20℃; for 2 h;
Stage #2: With sodium nitrite In water at -20 - 20℃; for 2 h;
Step 1: 2-bromo-3,5-dichloropyridine [0239] To a solution of 3,5-dichloropyridin-2-amine (1.0 g, 6.2 mmol) in 40percent aqueous HBr (8 mL) was added dropwise bromine (2.8 g, 17 mmol) at -20°C. The orange suspension was stirred for 2hrs at -20°C, and followed by addition of the aqueous NaN02 (1.1 g, 17 mmol) at -20°C. The mixture thus obtained was stirred for an additional 2 hours at ambient temperature. The brown mixture was basified with 30percent aqueous NaOH to pH ~12 at 0°C. The pale yellow mixture was extracted with ether. The combined organic phases were washed with brine, dried over Na2S04 and concentrated to afford the title compound as yellow solid (730 mg, 52percent). 1H NMR (400 MHz, CDC13) δ 8.27 (d, J J= 2.3 Hz, 1H).
Reference: [1] Patent: US4510148, 1985, A,
[2] Patent: WO2008/70908, 2008, A1, . Location in patent: Page/Page column 71-72
[3] Patent: WO2015/187845, 2015, A1, . Location in patent: Paragraph 0239
[4] European Journal of Medicinal Chemistry, 1989, vol. 24, # 3, p. 249 - 258
[5] Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 123 - 132
[6] Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4576 - 4587
  • 14
  • [ 4214-74-8 ]
  • [ 610278-88-1 ]
YieldReaction ConditionsOperation in experiment
63.7% at 20℃; Example 605-Cyano-furan-2-carboxylic acid[4-methyl-5'-(4-methyl-piperazin-l-yl)-3,4,5,6- tetrahydro-2H-[l,3']hipyridinyl-2 '-yl]-amide a) 3,5-dicholoro-2-nitro pyridine; 2-Amino-3,5-dichloropyridine (193 mg, 1.00 mmol) was dissolved in cone H2SO4 (5 mL) and K2S2O8 (1.3 g, 5.0 mmol) was added portionwise. The resulting mixture was stirred at RT overnight and poured onto crushed ice and neutralized with'satd aq NaHCO3. EPO <DP n="117"/>The product was extracted with CH2Cl2 (3x20 mL), dried (Na2SO4) and concentrated in vacuo to obtain the title compound (123 mg, 63.7percent). 1H-NMR (CDCl3; 400 MHz): δ 8.40 (d, IH , J= 2.1 Hz), 8.05 (d, IH, J= 2.1 Hz).
Reference: [1] Patent: WO2006/47504, 2006, A1, . Location in patent: Page/Page column 115-116
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1642 - 1648
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