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[ CAS No. 3430-27-1 ] {[proInfo.proName]}

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Chemical Structure| 3430-27-1
Chemical Structure| 3430-27-1
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Product Details of [ 3430-27-1 ]

CAS No. :3430-27-1 MDL No. :MFCD00128871
Formula : C6H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :IBKMZYWDWWIWEL-UHFFFAOYSA-N
M.W : 108.14 Pubchem ID :137935
Synonyms :

Calculated chemistry of [ 3430-27-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.61
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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 0.54
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 0.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.41
Solubility : 4.25 mg/ml ; 0.0393 mol/l
Class : Very soluble
Log S (Ali) : -0.93
Solubility : 12.7 mg/ml ; 0.118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.99
Solubility : 1.11 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 3430-27-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3430-27-1 ]

* 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 [ 3430-27-1 ]
  • Downstream synthetic route of [ 3430-27-1 ]

[ 3430-27-1 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 3430-27-1 ]
  • [ 399-88-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 2
  • [ 3430-27-1 ]
  • [ 540-80-7 ]
  • [ 109-63-7 ]
  • [ 38749-96-1 ]
YieldReaction ConditionsOperation in experiment
54% With Ki; sodium thiosulfate In 1,2-dimethoxyethane; acetonitrile; pentane 24b.
3-Iodo-4-methylpyridine
3-Amino-4-methylpyridine (2.0 g, 18.5 mmol) in DME (9.0 mL) was added dropwise to a solution of boron trifluoride diethyl etherate (3.4 mL, 27.7 mmol) in DME (35 mL) at -17° C.
After stirring for 15 min, t-butyl nitrite (2.6 mL, 22.2 mmol) in DME (37.0 mL) was carefully added to the reaction mixture while maintaining the temperature below -5° C.
After complete addition the temperature was allowed to gradually warm to 5° C. over 1 hr.
After recooling to -17° C., pentane was added and decanted.
The solid was triturated with pentane (2*) and Et2 O (2*), then the solvent was removed via positive N2 pressure to afford a white solid.
The crude diazonium tetrafluoroborate salt was dissolved in acetonitrile (70 mL) and KI (3.4 g, 20.3 mmol) was added at -10° C.
The reaction was allowed to gradually warm to ambient temperature and stir overnight.
A solution of 10percent sodium thiosulfate was carefully added to the reaction mixture, which was then poured over Et2 O and the phases separated.
The organic phase was dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; EtOAc/hexane, 1:15) to afford an amber oil (2.2 mg, 54percent): 1 H NMR (CDCl3, 300 MHz) δ2.42 (s, 3H), 7.19 (d, J=4.8 Hz, 1H), 8.38 (d, J=4.8 Hz, 1H), 8.86 (s, 1H).
Reference: [1] Patent: US5733912, 1998, A,
  • 3
  • [ 3430-27-1 ]
  • [ 38749-96-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 7, p. 1578 - 1581
  • 4
  • [ 3430-27-1 ]
  • [ 1121-19-3 ]
Reference: [1] Roczniki Chemii, 1956, vol. 30, p. 475,479[2] Chem.Abstr., 1957, p. 14722
  • 5
  • [ 5832-44-0 ]
  • [ 3430-27-1 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethyl acetate for 0.5 h; 4-Methyl-3-nitropyridine (3.642 g, 26.37 mmol; Lancaster) in ethyl acetate (36 mL) was treated with 10percent Pd/C (0.25 g) under a hydrogen atmosphere (60 psi) for 30 minutes. The catalyst was removed by filtration and the solution was concentrated to provide the title product as a white solid (2.92 g, 100percent). MS (DCI/NH3) m/z 109 (M+H)+.
Reference: [1] Patent: EP1428824, 2004, A1, . Location in patent: Page 42
[2] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104
[4] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
[5] Chemische Berichte, 1927, vol. 60, p. 2108
[6] Chemische Berichte, 1927, vol. 60, p. 2108
  • 6
  • [ 3430-22-6 ]
  • [ 3430-27-1 ]
YieldReaction ConditionsOperation in experiment
95% With ammonia; copper(II) sulfate In methanol at 160℃; for 8 h; Autoclave High pressure reactor was added 300 mL of methanol,150 g of 3-bromo-4-methylpyridine, 5g copper sulfate, pass ammonia to a pressure of 5 atm, heated to 160 ° C, reacted for 8 h, Cooled, filtered and the filtrate was concentrated under reduced pressure to give a solid which was recrystallized from ethyl acetate to give 89 g of 3-amino-4-methylpyridine in a yield of 95percent.
Reference: [1] Patent: CN106243022, 2016, A, . Location in patent: Paragraph 0070-0072
  • 7
  • [ 23056-39-5 ]
  • [ 3430-27-1 ]
YieldReaction ConditionsOperation in experiment
100% With sodium acetate In methanol EXAMPLE 39A
3-amino-4-methylpyridine
2-Chloro-3-nitro-4-methylpyridine (4.0 g, 23.2 mmol) in methanol was treated with 10percent palladium on carbon (2 g) and anhydrous sodium acetate (2.14 g, 26 mmol) and agitated under H2 (4 atm) at room temperature for 45 minutes.
The mixture was filtered and the filtrate concentrated under reduced pressure to provide the title compound (2.5 g, 100percent yield). MS (DCI/NH3) M/z 109 (M+H)+.
Reference: [1] Patent: US2002/19388, 2002, A1,
[2] Patent: US5733912, 1998, A,
[3] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 8
  • [ 129432-25-3 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 259 - 263
  • 9
  • [ 7250-52-4 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 259 - 263
[2] Patent: US5668287, 1997, A,
  • 10
  • [ 21901-40-6 ]
  • [ 3430-27-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 1, p. 115 - 118
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 11
  • [ 6635-86-5 ]
  • [ 3430-27-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 1, p. 115 - 118
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 12
  • [ 5832-44-0 ]
  • [ 7440-44-0 ]
  • [ 7440-05-3 ]
  • [ 3430-27-1 ]
Reference: [1] Patent: US2002/193596, 2002, A1,
  • 13
  • [ 76809-27-3 ]
  • [ 3430-27-1 ]
  • [ 69-72-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 14
  • [ 695-34-1 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 15
  • [ 108-89-4 ]
  • [ 3430-27-1 ]
Reference: [1] Patent: CN106243022, 2016, A,
  • 16
  • [ 23056-33-9 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 17
  • [ 21901-41-7 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 18
  • [ 21901-18-8 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 19
  • [ 856858-03-2 ]
  • [ 3430-27-1 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 192[2] Chem.Abstr., 1953, p. 6418
  • 20
  • [ 3222-50-2 ]
  • [ 3430-27-1 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 192[2] Chem.Abstr., 1953, p. 6418
  • 21
  • [ 55314-29-9 ]
  • [ 3430-27-1 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 192[2] Chem.Abstr., 1953, p. 6418
  • 22
  • [ 6316-67-2 ]
  • [ 3430-27-1 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 192[2] Chem.Abstr., 1953, p. 6418
  • 23
  • [ 3430-27-1 ]
  • [ 393-53-3 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 24
  • [ 3430-27-1 ]
  • [ 591-50-4 ]
  • [ 73183-34-3 ]
  • [ 19352-29-5 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
  • 25
  • [ 3430-27-1 ]
  • [ 40273-47-0 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 26
  • [ 3430-27-1 ]
  • [ 126325-50-6 ]
  • [ 126354-83-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
  • 27
  • [ 3430-27-1 ]
  • [ 133627-45-9 ]
YieldReaction ConditionsOperation in experiment
83.2%
Stage #1: With hydrogenchloride In water at 40℃; Cooling with ice
Stage #2: for 2 h;
First, 21.6 g of 3-amino-4-methylpyridine was added to the reaction kettle,In the cold water bath slowly dropping 72mL concentrated hydrochloric acid,Stirring to clarify after warming to 40 ° C, 30 ~ 60min slowly dropping 30mL 30percent hydrogen peroxide, temperature control reaction 2h.After completion of the reaction, the system ρΗ = 3 was adjusted with 45percent sodium hydroxide solution, extracted with trichloromethane, dried and removed to obtain the crude product. Recrystallization from petroleum ether or n-hexane gave white or pale yellow needle-like crystals of 2-chloro-3-amino-4-methylpyridine with a purity of 99.0percent, a yield of 83.2percent
78%
Stage #1: With hydrogenchloride; dihydrogen peroxide In water at 20℃;
Step 2[00286] 2-chloro-4-methyl-pyridin-3 -ylamine : A solution of 4-methylpyridin-3 -amine(200 g, 1.85 mol, 1.00 equiv) in concentrated hydrochloric acid (3 L) was placed in a 5 L 3- necked round-bottom flask. Hydrogen peroxide (30percent) (210 g, 1.85 mol, 1.00 equiv) was added dropwise to the solution while maintaining the temperature at 20 °C. The resulting solution was allowed to react overnight at ambient temperature. Saturated aqueous sodium carbonate was added to the solution, till a pH of 8 was reached. The solution was filtered, and the filter cake was washed with water (100 ml x3). The filter cake was dissolved in ethyl acetate (300OmL) and dried over sodium sulfate. The solution was filtered, and the filtrate was concentrated in vacuo <n="74"/>using a rotary evaporator. The product (204.6 g, purity: 90percent, yield:78percent) of 2-chloro-4-methyl- pyridin-3-ylamine was obtained as a light red solid. The material was used in next step without further purification.
84% With hydrogenchloride; sodium hydroxide; chlorine In water F)
Preparation of 3-Amino-2-Chloro-4-Methylpyridine STR16
3-Amino-4-methylpyridine (21.6 g, 0.2 mole) was suspended in 75 ml of water at room temperature.
The mixture was dissolved by the addition of 25 ml conc. hydrochloric acid.
The solution was cooled to 20° C. and 15.6 g (0.22 mole) of chlorine gas was introduced through an inlet tube reaching below the surface of the reaction mixture over 25 minutes.
The mixture was stirred under a nitrogen purge for an additional 30 minutes, then cooled to 10° C. and basified by the addition of 70 mL of a 12.5 N. sodium hydroxide solution.
Additional water (100 mL) was added to maintain efficient agitation of the mixture.
The precipitate was collected, washed with water and dried to give 14.5 g of the title product.
The aqueous phase was extracted with 3 times 100 mL of methylene chloride.
The organic phases were washed with water, dried over magnesium sulfate, and concentrated to give an additional 9.4 g, mp 62-64° C. Total yield, 23.9 g (84percent).
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104
[2] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 259 - 263
[3] Patent: CN106243022, 2016, A, . Location in patent: Paragraph 0076-0078
[4] Patent: WO2008/103899, 2008, A1, . Location in patent: Page/Page column 72-73
[5] Patent: US5200522, 1993, A,
[6] Patent: US5668287, 1997, A,
[7] Patent: US2011/319394, 2011, A1, . Location in patent: Page/Page column 70
  • 28
  • [ 3430-27-1 ]
  • [ 133627-47-1 ]
Reference: [1] Patent: WO2008/103899, 2008, A1,
  • 29
  • [ 3430-27-1 ]
  • [ 477600-70-7 ]
Reference: [1] Patent: CN108610279, 2018, A,
  • 30
  • [ 3430-27-1 ]
  • [ 1072249-89-8 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 18, p. 6396 - 6402
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