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Chemical Structure| 6945-68-2
Chemical Structure| 6945-68-2
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Product Details of [ 6945-68-2 ]

CAS No. :6945-68-2 MDL No. :MFCD00047441
Formula : C5H4BrN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QOOCOFOGYRQPPN-UHFFFAOYSA-N
M.W : 218.01 Pubchem ID :138878
Synonyms :
5-Bromo-3-nitro-2-pyridinamine

Calculated chemistry of [ 6945-68-2 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 45.16
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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : -0.11
Log Po/w (SILICOS-IT) : -0.73
Consensus Log Po/w : 0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.651 mg/ml ; 0.00299 mol/l
Class : Soluble
Log S (Ali) : -2.97
Solubility : 0.234 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.91
Solubility : 2.71 mg/ml ; 0.0124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 6945-68-2 ]

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 [ 6945-68-2 ]

* 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 [ 6945-68-2 ]
  • Downstream synthetic route of [ 6945-68-2 ]

[ 6945-68-2 ] Synthesis Path-Upstream   1~28

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Reference: [1] Patent: US5624935, 1997, A,
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
[2] Journal of the Chemical Society, 1952, p. 2042,2044
[3] Journal of the Chemical Society, 1952, p. 2042,2044
[4] Journal of the Chemical Society, 1952, p. 2042,2044
  • 3
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Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 9, p. 1036 - 1040
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YieldReaction ConditionsOperation in experiment
95% With aluminum (III) chloride; water; iron In isopropyl alcohol at 90℃; for 0.75 h; EXAMPLE 2; Representative Procedures for the Synthesis of a 1,4-Benzodiazepinone bearing a C5-1H- Imidazo[4,5-b]pyridin-2(3H)-one Group; .Part I: Synthesis of Imidazo[4,5-b]pyridin-2(3H)-one Boronic Acid; Step 1 5-Bromopyridine-2,3-diamine. 5-Bromo-3-nitropyridin-2-amine (3 g) was dissolved in isopropyl alcohol (56 mL) and water (28 mL). Ammonium chloride (1.47 g, 2 eq) was added followed by iron powder (2.31 g, 3 eq). The reaction was heated to 90 0C for 45 minutes. The solution was then cooled, and diluted with EtOAc, filtered, and the layers were separated. The organic layer was then washed with brine, dried over sodium sulfate, and concentrated delivering product as a solid (2.45 g, 95percent yield). 1H-NMR (300 MHz, DMSO-d6) δ 7.25 (d, IH), 6.77 (d, IH), 5.70 - 5.40 (bs, 2H), 5.20 - 4.80 (bs, 2H).
87%
Stage #1: With hydrogenchloride; iron In ethanol; water at 0 - 80℃; for 1 h;
Stage #2: With sodium hydroxide In ethanol; water at 0℃;
Reference Example 1
A suspension of 2-amino-5-bromo-3-nitropyridine (21.0 g), iron filings (26.9 g) and ethanol (150 ml) was cooled with ice, and to the suspension was added dropwise concentrated hydrochloric acid (20 ml)..
After the dropwise addition, the mixture was stirred at room temperature for 10 minutes and at 80°C for 50 minutes..
The reaction mixture was poured onto ice, neutralized with 8 N sodium hydroxide, and extracted with ethyl acetate - tetrahydrofuran (3: 1, v/v) (at that time, insolubles were filtered off by using celite)..
The organic layer was dried over MgSO4, the solvent was distilled off under reduced pressure, and crystals were collected by filtration to obtain 2,3-diamino-5-bromopyridine (15.8 g, 87 percent).1H NMR (CDCl3) δ 3.38 (2H, broad s), 4.21 (2H, broad s), 7.01 (1H, d, J = 2.2 Hz), 7.69 (1H, d, J = 2.2 Hz) ppm IR (KBr) ν 3179, 1632, 1476 cm-1
50% With hydrogenchloride; iron In ethanol; water for 2 h; Heating / reflux The title compound was prepared essentially as described by Petrow. et al., [J.] Chem. Soc. (1948) 1389, [1391.] A mixture of 2-amino-5-bromo-3-nitropyridine (62.2 g, 285 mmol), iron powder (171 g, 3.06 mol), concentrated hydrochloric acid (2.85 ml), water (60 [ML)] and ethanol (230 ml) was refluxed for 2 h, filtered whilst warm, the solids washed twice with ethanol (2 x 150 ml) and the combined ethanol solutions were evaporated to dryness. The crude solid was recrystallized from water, using decolourising charcoal, filtered whilst warm, the solids washed twice with warm ethanol (2 x 100 [ML),] the ethanol evaporated off and the precipitate was filtered off, washed with water (3 x 75 ml) and dried to afford the title compound (27 g, 50percent). 'H NMR [(DMSO-D6)] : [No. ] 7.26 (1H, d); 6.78 (1H, d); 5.57 (2H, s); 4.97 (2H, s). APCI-MS m/z : 188.1/190. 1 [MH+].
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 18, p. 3524 - 3535
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[3] Patent: WO2010/121164, 2010, A2, . Location in patent: Page/Page column 60
[4] Patent: EP1460067, 2004, A1, . Location in patent: Page 29
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1160 - 1170
[6] Patent: WO2004/16611, 2004, A1, . Location in patent: Page 47-48
[7] Journal of the American Chemical Society, 1957, vol. 79, p. 6421,6423,6424
[8] Journal of the Chemical Society, <1948> 1389, 1391,
[9] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2599 - 2606
[10] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3052 - 3066
[11] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6216 - 6219
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YieldReaction ConditionsOperation in experiment
93% With hydrazine In methanol; ethyl acetate Step BBB: 5-Bromo-2,3-diaminopyridine
2-Amino-5-bromo-3-nitropyridine (3.5 g, 16.1 mmol) was combined with FeCl3.6H2 O (0.217 g, 0.8 mmol) and activated charcoal (1.6 g) to which dry methanol (160 mL) was added.
The mixture was heated to 70° C. for 10 min, cooled to ambient temperature followed by the dropwise addition of hydrazine (2.57 g, 80.3 mmol) over 5 min.
Heating was resumed and the reaction was maintained at 70° C. for 2 h.
After cooling to ambient temperature, the reaction contents were filtered through a pad of celite.(R)., eluted with methanol followed by removal of the solvent in vacuo.
The residue was dissolved in ethyl acetate and washed with H2 O, brine, dried (Na2 SO4), filtered, concentrated in vacuo, and the crude reside was purified by flash chromatography on silica gel using a gradient elution (10, 20, 40, 60, and 80percent ethyl acetate/hexanes).
According to this procedure, 2.8 g (93percent yield) of the title compound was obtained.
Reference: [1] Patent: US6025366, 2000, A,
[2] Patent: US6110931, 2000, A,
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Reference: [1] Patent: EP1226138, 2004, B1,
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Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 2, p. 261 - 268
[2] Journal of the Chemical Society, 1952, p. 2042,2044
[3] Journal of the Chemical Society, 1952, p. 2042,2044
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Journal of the Chemical Society, 1952, p. 2042,2044
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
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YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.75 h;
Stage #2: With hydrogenchloride; copper(l) chloride In water at 0 - 70℃;
EXAMPLE 1
6-(Furan-3-yl)-3-[3-(pyridin-3-yl)phenyl]-3 H -imidazo[4,5- b ]pyridine
2-Amino-5-bromo-3-nitropyridine (21.8 g, 0.1 mol) was ground to a fine powder using a mortar and pestle and then suspended in 6M hydrochloric acid (250 ml).
This mixture was cooled to 0°C and treated with solid NaNO2 (8.3 g, 0.12 mol) at such a rate that the internal temperature remained below 5°C (ca. 45 minutes).
Following the addition, stirring at 0°C was continued for a further 1 hour.
To the resultant suspension was added a solution of freshly prepared copper(I) chloride (12.9 g, 0.13 mol) in degassed 38percent hydrochloric acid and the reaction stirred to ambient temperature over 90 minutes before heating the reaction to 70°C to complete the decomposition of the diazonium salt.
The reaction was cooled, diluted with water (750 ml) and then air was passed through the mixture for 30 minutes before adding 0.88 ammonia to ca. pH 9.
The blue mixture was shaken with diethyl ether (600 ml) and any remaining solids removed by filtration.
The organic layer was then washed with 5percent aqueous ammonia, water, brine and dried over anhydrous sodium sulphate.
This solution was filtered and then pre-adsorbed on to silica.
Purification by dry flash chromatography eluding with isohexane and a gradient of ethyl acetate from 5percent to 20percent gave 5-bromo-2-chloro-3-nitropyridine as a pale yellow solid (13.1 g, 55percent) followed by recovered starting material (6.4 g); δH (400 MHz, CDCl3) 8.36 (1H, d, J 1, H-6), 8.69 (1H, d, J 1, H-4).
Reference: [1] Patent: WO2007/129044, 2007, A1, . Location in patent: Page/Page column 77
[2] Patent: EP1214319, 2003, B1, . Location in patent: Page/Page column 13
[3] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 2, p. 261 - 268
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Journal of the Chemical Society, 1952, p. 2042,2044
[6] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
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YieldReaction ConditionsOperation in experiment
58.9%
Stage #1: With hydrogen bromide In water at 0 - 5℃;
Stage #2: at 0℃; for 0.75 h;
Stage #3: With sodium hydroxide In water at 20℃; for 1 h;
(1) Production of 2,5-dibromo-3-nitropyridine: Hydrogen bromide (48 percent in H2O, 13 mL) was stirred at 0°C, to which 5-bromo-3-nitropyridin-2-amine (5.0 g, 22.9 mmol) was dropwise added with its inner temperature kept at 5°C or lower. After the addition, bromine (4.69 mL) and sodium sulfite (6.32 g) were added to it in that order. After stirred at 0°C for 45 minutes, aqueous sodium hydroxide (9.16 g) solution (10 mL) was added thereto and stirred at room temperature for 1 hour. The resulting solid was taken out through filtration, washed with water and dried to obtain the intended compound (3.80 g, 58.9 percent).
35%
Stage #1: With hydrogen bromide; bromine In water at 0℃;
Stage #2: With sodium nitrite In water at 0℃;
Stage #3: With sodium hydroxide In waterCooling with ice
Synthesis Example 2; Synthesis of N-ethyl-N-methyl-N'[2,5-dimethyl-6-(4-t-butylphenyl)pyridin-3- y 1] formamidine (Compound No .11); (1); Bromine (68.81 mmol, 3.5 ml) was gradually added dropwise to an aqueous solution of 48percent hydrobromic acid (120 ml) of 2-amino-5-bromo-3-nitropyridine (22.93 mmol, 5.0 g) at 0°C, followed by stirring at the same temperature for 1 hour. An aqueous solution prepared by dissolving sodium nitrite (57.34 mmol, 4.0 g) in 60 ml of water was gradually added dropwise, followed by stirring at the same temperature for1.5 hours. To the resulting reaction mixture, 10 mol/liter sodium hydroxide aqueous solution was added on ice to neutralize, and an aqueous layer was extracted with ethyl acetate. An organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and filtered, followed by distilling away a solvent under reduced pressure. The resulting crude product was purified with column chromatography to obtain 2.24 g of 2,5-dibromo-3-nitropyridine (yield 35percent). 1H NMR δ ppm (300 MHz, CDCl3) data of this compound are 8.66 (d, 2H, J=2.4Hz), 8.27 (d, 2H, J=2.1Hz).
Reference: [1] Patent: EP1757594, 2007, A1, . Location in patent: Page/Page column 76
[2] Patent: WO2009/88103, 2009, A1, . Location in patent: Page/Page column 16
[3] Tetrahedron, 2003, vol. 59, # 43, p. 8555 - 8570
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Patent: US2009/69319, 2009, A1, . Location in patent: Page/Page column 31
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Reference: [1] Patent: WO2004/55003, 2004, A1, . Location in patent: Page 65-66
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
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Reference: [1] Patent: US5624935, 1997, A,
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YieldReaction ConditionsOperation in experiment
71% at 0 - 20℃; Inert atmosphere General procedure: 2-Aminopyridine 7 (0.020 mol) was added to ice-cold concentrated sulfuric acid and the resulting solution was treated with concentrated nitric acid (1.09 mL, 0.024 mol), which was added slowly so as to maintain the reaction temperature in 0-5 °C range.The resulting solution was stirred at 0-5 °C for 1 h, warmed up to rt and stirred at that temperature overnight. It was then poured over ice and the pH was adjusted to 7-8 with 10percent aq NaOH solution. The resulting precipitate was collected by filtration, washed with water and dried at 60 °C overnight to provide analytically pure 2-amino-3-nitropyridines.
63% With sodium hydroxide; sulfuric acid; nitric acid In ice-water Step AAA: 2-Amino-5-bromo-3-nitropyridine
Sulfuric acid (290 mL) was cooled to 0° C., followed by the slow addition of 2-amino-5-bromopyridine (50 g, 289 mmol).
Nitric acid (15 mL) was added dropwise over 30 min with the aid of a pressure-equalized dropping funnel.
After 90 min at 0° C., the reaction mixture was heated to 75° C. for 2 h.
After cooling to ambient temperature, the reaction mixture was poured into 1500 mL of ice-water and neutralized to pH 8 with 50percent NaOH (w/w).
The precipitate formed was collected on a fritted funnel, washed with 1000 mL cold water, and dried in vacuo, which provided 39.7 g of the title compound (63percent yield).
Reference: [1] Chemical Communications, 2013, vol. 49, # 72, p. 7929 - 7931
[2] Tetrahedron, 2003, vol. 59, # 43, p. 8555 - 8570
[3] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
[4] Patent: US6025366, 2000, A,
[5] Journal of the Chemical Society, 1948, p. 1389,1392
[6] Yakugaku Zasshi, 1959, vol. 79, p. 1129,1132[7] Chem.Abstr., 1960, p. 3418
[8] Patent: US6110931, 2000, A,
[9] Patent: US5624935, 1997, A,
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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
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Reference: [1] Patent: US5624935, 1997, A,
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Reference: [1] Polish Journal of Chemistry, 1995, vol. 69, # 4, p. 605 - 611
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Reference: [1] Polish Journal of Chemistry, 1995, vol. 69, # 4, p. 605 - 611
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Reference: [1] Chemical Communications, 2013, vol. 49, # 72, p. 7929 - 7931
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
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Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 489[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1021
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Reference: [1] Yakugaku Zasshi, 1959, vol. 79, p. 1129,1132[2] Chem.Abstr., 1960, p. 3418
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YieldReaction ConditionsOperation in experiment
89% With sulfuric acid; sodium nitrite In water at 0 - 20℃; Inert atmosphere General procedure: 2-Amino-3-nitropyridine 8 (0.015 mol) was dissolved, on cooling with ice, in 70percent sulfuric acid and treated with a solution of NaNO2 (1.24 g) in water (8 mL), which was added dropwise so as to maintain the reaction temperature in 0-5 °C range. The reaction was allowed to warm up to rt and stirred at that temperature for 3 h. The precipitate formed was isolated by filtration, washed with water and dried at 60 °C overnight.
Reference: [1] Tetrahedron, 2014, vol. 70, # 5, p. 1077 - 1083
[2] Journal of the Chemical Society, 1952, p. 2042,2044
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 9, p. 1036 - 1040
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Reference: [1] Patent: WO2015/92713, 2015, A1,
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  • [ 122-51-0 ]
  • [ 28279-49-4 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 31, p. 4054 - 4057
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Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
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Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3052 - 3066
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