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Product Details of [ 4214-75-9 ]

CAS No. :4214-75-9 MDL No. :MFCD00006314
Formula : C5H5N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BPYHGTCRXDWOIQ-UHFFFAOYSA-N
M.W : 139.11 Pubchem ID :77887
Synonyms :
3-Nitropyridin-2-ylamine

Calculated chemistry of [ 4214-75-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.46
TPSA : 84.73 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
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) : 0.64
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 0.58
Log Po/w (MLOGP) : -0.94
Log Po/w (SILICOS-IT) : -1.44
Consensus Log Po/w : -0.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 3.22 mg/ml ; 0.0232 mol/l
Class : Very soluble
Log S (Ali) : -2.24
Solubility : 0.794 mg/ml ; 0.00571 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.02
Solubility : 13.3 mg/ml ; 0.0957 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 4214-75-9 ]

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 [ 4214-75-9 ]

* 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 [ 4214-75-9 ]
  • Downstream synthetic route of [ 4214-75-9 ]

[ 4214-75-9 ] Synthesis Path-Upstream   1~35

  • 1
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  • [ 68175-07-5 ]
Reference: [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
  • 2
  • [ 4214-75-9 ]
  • [ 40851-92-1 ]
Reference: [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
[3] Chemische Berichte, 1927, vol. 60, p. 775[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
  • 3
  • [ 4214-75-9 ]
  • [ 13534-89-9 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 4
  • [ 4214-75-9 ]
  • [ 39856-58-1 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 5
  • [ 4214-75-9 ]
  • [ 452-58-4 ]
  • [ 40851-95-4 ]
Reference: [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
  • 6
  • [ 5470-18-8 ]
  • [ 4214-75-9 ]
YieldReaction ConditionsOperation in experiment
97% at 90℃; for 16 h; Sealed tube 3-Nitropyridin-2-amine (1): 2-chloro-3-nitropyridine (4 g, 25.23 mmol) was taken in a sealed tube and aqueous NH3 (8.57 g, 504.6 mmol) was added. The reaction mixture was heated to 90 °C and stirred for 16 h. The reaction mass was then cooled to 0 °C and filtered to obtain 1 (3.4 g, 97percent) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): δ 6.74 (m, 1H), 7.87 (s, 2H), 8.38 (m, 2H). MS m/z (M+H): 140.3
Reference: [1] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 001189
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 669 - 672
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1696 - 1701
  • 7
  • [ 1480-87-1 ]
  • [ 4214-75-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7564 - 7567
  • 8
  • [ 133520-08-8 ]
  • [ 4214-75-9 ]
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
  • 9
  • [ 20265-35-4 ]
  • [ 4214-75-9 ]
Reference: [1] Patent: US4552967, 1985, A,
  • 10
  • [ 504-29-0 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 805 - 809
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 527
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 1240[4] Chem. Zentralbl., 1915, vol. 86, # I, p. 1066
[5] Chemische Berichte, 1952, vol. 85, p. 1012,1019
[6] Journal of the American Chemical Society, 1955, vol. 77, p. 3154
[7] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 10, p. 3597 - 3602
[8] Journal of Molecular Structure, 2013, vol. 1043, p. 15 - 27
[9] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 528
[10] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 528
  • 11
  • [ 71090-35-2 ]
  • [ 13070-22-9 ]
  • [ 4214-75-9 ]
Reference: [1] Liebigs Annalen der Chemie, 1986, # 2, p. 380 - 383
  • 12
  • [ 5470-18-8 ]
  • [ 77287-34-4 ]
  • [ 4214-75-9 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 8, p. 1439 - 1445
  • 13
  • [ 2530-26-9 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
  • [ 1681-37-4 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 26, p. 4393 - 4395
  • 14
  • [ 2530-26-9 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
  • [ 3346-63-2 ]
  • [ 1681-37-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
[2] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 15
  • [ 26482-54-2 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
Reference: [1] Acta Chimica Hungarica, 1983, vol. 113, # 2, p. 159 - 164
[2] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2035 - 2040
  • 16
  • [ 7664-93-9 ]
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  • [ 4214-75-9 ]
Reference: [1] Chemische Berichte, 1928, vol. 61, p. 1812
  • 17
  • [ 26482-54-2 ]
  • [ 7664-93-9 ]
  • [ 142-08-5 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915, vol. 47, p. 1290[4] Chem. Zentralbl., 1916, vol. 87, # II, p. 15
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 345[6] Chemische Berichte, 1927, vol. 60, p. 2437
  • 18
  • [ 4214-75-9 ]
  • [ 6332-56-5 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 3, p. 592 - 594
[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476[3] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 534
  • 19
  • [ 4214-75-9 ]
  • [ 1480-87-1 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 1, p. 23 - 36
[2] Journal of Fluorine Chemistry, 1988, vol. 38, p. 435 - 438
  • 20
  • [ 4214-75-9 ]
  • [ 5470-18-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020
  • 21
  • [ 7647-01-0 ]
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  • [ 5470-18-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020
  • 22
  • [ 4214-75-9 ]
  • [ 19755-53-4 ]
YieldReaction ConditionsOperation in experiment
45% With potassium nitrite; hydrogen bromide; copper(I) bromide In water; dimethyl sulfoxide at 35℃; for 4 h; A solution of 48percent aq. HBr (3.60 mL, 32.0 mmol) dissolved in DMSO (35 mL) was added dropwise to a solution of 3-nitropyridine-2-amine 10, (1.0 g, 7.19 mmol) in a mixture of 35 mL of DMSO, KNO2 (2.45 g, 28.75 mmol) and CuBr (0.206 g, 1.44 mmol) at 35 °C with stirring. The added mixture was stirred at 35 °C for 4 h and then transferred to a solution of K2CO3 (7 g) in 100 mL of ice water. The reaction mixture was then taken up in diethyl ether, and the ethereal extracts were washed with water and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure gave the crude product. The crude product was purified by silica gel chromatography (eluent: 100percent dichloromethane) to give 2-bromo-3-nitropyridine 11 as a beige powder (0.662 g, 45percent). Rf = 0.75 (dichloromethane); mp 121-122 °C (lit. [12] : 123-124 °C); IR (KBr) νmax (cm-1): 3042 (νCHar), 1578 and 1562 (νC=C), 1524 (νasNO2), 1350 (νsy NO2); 1H NMR (400 MHz, DMSO-d6): δ 8.73 (dd, 1H, J1 = 1.6 Hz, J2 = 4.8 Hz, H-6), 8.54 (dd, 1H, J1 = 1.6 Hz, J3 = 8.0 Hz, H-4), 7.79 (dd, 1H, J2 = 4.8 Hz, J3 = 8.0 Hz, H-5); 13C NMR (100 MHz, DMSO-d6): δ 153.26 (C-6), 147.08 (C-3), 134.48 (C-4), 132.08 (C-2), 124.44 (C-5); MS (ESI) m/z (percent): 202.9 (100) [M + H]+, 204.9 (100) [M + H + 2]+. Anal. calcd for C5H3BrN2O2: C, 29.58; H, 1.49; N, 13.80. Found: C, 29.63; H, 1.50; N, 13.83.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 171 - 183
[2] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
[3] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219
  • 23
  • [ 4214-75-9 ]
  • [ 73895-37-1 ]
Reference: [1] Chemische Berichte, 1927, vol. 60, p. 775[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
[3] Chemische Berichte, 1927, vol. 60, p. 775[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1927, vol. 59, p. 417
  • 24
  • [ 4214-75-9 ]
  • [ 51315-07-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 171 - 183
  • 25
  • [ 4214-75-9 ]
  • [ 74-88-4 ]
  • [ 4093-88-3 ]
Reference: [1] Chemische Berichte, 1928, vol. 61, p. 1230[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 975
[3] Chemische Berichte, 1928, vol. 61, p. 1230[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 975
  • 26
  • [ 4214-75-9 ]
  • [ 3073-30-1 ]
Reference: [1] Patent: US5223499, 1993, A,
[2] Patent: US5412097, 1995, A,
  • 27
  • [ 2530-26-9 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
  • [ 1681-37-4 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 26, p. 4393 - 4395
  • 28
  • [ 2530-26-9 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
  • [ 3346-63-2 ]
  • [ 1681-37-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
[2] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
  • 29
  • [ 4214-75-9 ]
  • [ 6945-68-2 ]
YieldReaction ConditionsOperation in experiment
56% With dihydrogen peroxide; 1-butylpyridinium bromide; toluene-4-sulfonic acid In 1,2-dimethoxyethane at 80℃; for 24 h; Schlenk technique; Inert atmosphere; Green chemistry General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80°C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5058 - 5061
[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 494[3] Chem. Zentralbl., 1923, vol. 94, # III, p. 1021
  • 30
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  • [ 25391-57-5 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With sulfuric acid; acetic acid; periodic acid In water at 90℃; for 0.166667 h;
Stage #2: With iodine In water for 60 h;
A 250 ml three-necked flask was charged with 2-amino-3-nitropyridine (10.0 g, 72.0 mmol),Acetic acid (44 mL) and water (10 mL).90 when addedPeriodic acid (3.28 g, 14.4 mmol)And the mass percentage concentration of 98percent concentrated sulfuric acid(1.3 mL); after stirring for 10 minutes, iodine (9.1 g, 36.0 mmol),Continue stirring at this temperature for 60 minutes. After cooling to room temperature,The reaction solution was added to a saturated aqueous solution of sodium thiosulfate (100 mL); separated by filtration,The solid was washed with saturated brine (50 mL x 2) and petroleum ether (50 mL x 2).The crude product was recrystallized from a mixture of petroleum ether and ethyl acetate (volume ratio: 5: 1)A yellow solid, high purity compound 1 (17.57 g, 69.1 mmol, 96percent) was obtained.
57%
Stage #1: at 90℃; for 0.25 h;
Stage #2: at 90℃; for 1 h;
a) 5-Iodo-3-nitropyridin-2-amineTo a solution of 3-nitropyridin-2-amine (1.2 g, 8.63 mmol) in acetic acid (5 ml), water (1 ml) and sulfuric acid (0.2 ml) was added periodic acid (0.4 g, 1.72 mmol, 0.2 eq.) and the mixture was stirred at 90 °C for 15 min. Iodine (0.87 g, 3.45 mmol, 0.4 eq.) was added portionwise and the mixture was heated at 90 °C for 1 h. The mixture was quenched by the addition of water and extracted with ethylacetate (3 χ 150 ml). The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate. The solvent was distilled off to give the product in 57 percent yield (1.3 g). 1H NMR (300 MHz, DMSO-< ): δ 8.58 (d, 1H), 8.54 (d, 1H) 8.04 (br s, 2H); LC-MS (ESI); Calculated mass: 265.01 : Observed mass: 265.9 [M+H]+ (rt: 1.36 min).
57%
Stage #1: With sulfuric acid; acetic acid; periodic acid In water at 90℃; for 0.25 h;
Stage #2: With iodine In water at 90℃; for 1 h;
To a solution of 3-nitropyridin-2-amine (1.2 g, 8.63 mmol) in acetic acid (5 ml), water (1 ml) and sulfuric acid (0.2 ml) was added periodic acid (0.4 g, 1.72 mmol, 0.2 eq.) and the mixture was stirred at 90° C. for 15 min.
Iodine (0.87 g, 3.45 mmol, 0.4 eq.) was added portionwise and the mixture was heated at 90° C. for 1 h.
The mixture was quenched by the addition of water and extracted with ethylacetate (3*150 ml).
The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate.
The solvent was distilled off to give the product in 57percent yield (1.3 g).
1H NMR (300 MHz, DMSO-d6): δ 8.58 (d, 1H), 8.54 (d, 1H) 8.04 (br s, 2H); LC-MS (ESI); Calculated mass: 265.01: Observed mass: 265.9 [M+H]+ (rt: 1.36 min).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[2] Patent: CN107325045, 2017, A, . Location in patent: Paragraph 0006; 0009
[3] Patent: WO2013/53983, 2013, A1, . Location in patent: Page/Page column 37
[4] Patent: US2015/11548, 2015, A1, . Location in patent: Paragraph 0152
  • 31
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YieldReaction ConditionsOperation in experiment
79% With sulfuric acid; acetic acid In water 5-Iodo-3-nitro-2-aminopyridine
A mixture of 2-amino-3-nitropyridine (5.0 g, 35.9 mmol), acetic acid (22 mL), water (5 mL), sulfuric acid (0.650 mL), and HIO4*2H2O (1.7 g, 7.5 mmol) was allowed to stir at 90° C. for 10 min.
Iodine crystals (3.7 g, 14.6 mmol) were added in portions.
After stirring for 1 h, the reaction was poured into saturated sodium thiosulfate and extracted with ethyl acetate.
The organic layers were washed with 0.1 M NaOH and saturated brine, dried with sodium sulfate, then evaporated to give orange solid (7.5 g, 79percent yield).
mp 213-215° C.; 1H NMR (DMSO) δ (ppm) 8.03 (br s, 2H), 8.53 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H); 13C NMR (DMSO) δ (ppm) 74.18, 127.92, 141.31, 152.50, 160.88.
Analytical Calculated for C5H4O2N3I: C, 22.66; H, 1.52; N, 15.86; Found: C, 22.88; H, 1.53; N, 15.69.
Reference: [1] Patent: US6538010, 2003, B1,
  • 32
  • [ 4214-75-9 ]
  • [ 452972-08-6 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 33
  • [ 4214-75-9 ]
  • [ 426463-09-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
  • 34
  • [ 4214-75-9 ]
  • [ 426463-05-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[2] Patent: US2015/11548, 2015, A1,
[3] Patent: WO2013/53983, 2013, A1,
  • 35
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  • [ 211555-30-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9839 - 9842
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