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CAS No. : | 38875-53-5 | MDL No. : | MFCD00460094 |
Formula : | C5H6BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YRGMYJUKFJPNPD-UHFFFAOYSA-N |
M.W : | 188.03 | Pubchem ID : | 691156 |
Synonyms : |
|
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 : | 2.0 |
Molar Refractivity : | 40.75 |
TPSA : | 64.93 Ų |
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) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 1.19 |
Log Po/w (XLOGP3) : | 0.51 |
Log Po/w (WLOGP) : | 1.02 |
Log Po/w (MLOGP) : | 0.37 |
Log Po/w (SILICOS-IT) : | 0.67 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.82 |
Solubility : | 2.84 mg/ml ; 0.0151 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.44 |
Solubility : | 6.76 mg/ml ; 0.036 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.16 |
Solubility : | 1.3 mg/ml ; 0.0069 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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+]. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | for 48 h; | INTERMEDIATE 197-Bromopyrido[2,3-fr1pyrazine 2,3-Diamino-5-bromopyridine (2 g, 10.6 mmol) was dissolved in ethanol (25 mL) and glyoxal (5 mL, 40percent in water) was added. After standing for 48 h the mixture was concentrated in vacuo and the residue triturated with diethyl ether to give, after air-drying, the title compound (2.04 g, 92percent) as a pink-brown solid. δH (d6 DMSO) 9.28 (d, IH), 9.20 (d, IH), 9.12 (d, IH), 8.95 (d, IH). LCMS (ES+) 212 (M+H)+, RT 1.98 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | at 80℃; for 16 h; | To a solution of 2,3-diamino-5-bromopyridine (5 g, 27 mmol) in THF (87 mL) was added CDI (3.02 g, 18.6 mmol), and the reaction mixture was stirred at 80 °C for 16 h. Then, water was added, and the mixture was filtered. The solids were collected by filtration, washed with water and Et2O, and dried under vacuum to afford the title compound (5.3 g, 25 mmol, 93percent), which was used in the next step without further purification. MS (ESI): mass calcd. for C6H4BrN3O, 212.95; m/z found, 214 [M+H]+. |
92% | at 20℃; Inert atmosphere | Step 2 6-Bromo-lH-imidazo[4,5-b]pyridin-2(3H)-one. 5-Bromopyridine-2,3-diamine (2.45 g) was dissolved in THF (25 niL) and l,l'-carbonyldiimidazole (2.54 g, 1.2 eq) was added. The reaction was stirred at room temperature under nitrogen gas overnight. Water was then added to the mixture and the product was collected by filtration. The solid was dried under vacuum delivering product (2.57 g, 92percent yield). 1H-NMR (300 MHz, DMSOd6) δ 11.50 (s, IH), 11.00 (s, IH), 7.93 (s, 1 H), 7.39 (s, IH). MS (ES+) m/z 213.1 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | at 100℃; for 16 h; | A mixture of 5-bromopyridine-2,3 -diamine (2 g, 10.6 mmol) and urea (2.5 g, 41.6 mmol) was dissolved in DMF and heated to 100 °C for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over a2S04 then concentrated to provide 6-bromo-lH-imidazo[4,5- b]pyridin-2(3H)-one (0.80 g, 36 percent) as an off white solid which was used without further purification. LCMS Method W: retention time 0.98 min; [M+2] = 212, 214.0. |
9 g | at 180℃; for 16 h; | To a stirred solution of compound 1(10 g) in DMF was added urea (8g) and the total reaction mass stirred at 180° c for 16hrs.cooled to RT and concentrated under vacuum to get desired compound 2 (9 g ) |
9 g | at 180℃; for 16 h; | Step-1 [0065] To a stirred solution of compound 1 (10 g) in DMF was added urea (8 g) and the total reaction mass stirred at 180° c. for 16 hrs. cooled to RT and concentrated under vacuum to get desired compound 2 (9 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 100℃; for 3 h; | Example 11; 217 218 219Part AA solution of compound 217 (1.00 g, 5.32 mmol), formic acid (0.5 mL) and triethyl orthoformate (15 mL) were stirred at 1000C for 3 hours at which time LC-MS analysis indicated that the reaction was complete. The reaction mixture was concentrated under vacuum. Purification by column chromatography (10percent MeOH / DCM) afforded compound 218 as a beige solid 1.01g (96percent). 1H NMR (400 MHz, DMSO-d6) δ 8.46 (s, 1 H), 8.41 (d, 1 H), 8.27 (d, 1 H). |
95% | for 10 h; Reflux | Preparative Example 23 Step 1: 6-bromo-3H-imidazo[4,5-b]pyridine A solution of 5-bromopyridine-2,3-diamine (10.0 g, 53.0 mmol) in formic acid (96percent, 100 mL) was heated to reflux for 10 h and subsequently concentrated to dryness in vacuo. The residue was taken up in water and the title compound was collected as a solid by filtration, washed with water (2 x 30 niL) and dried to afford 6-bromo-3H-imidazo[4,5-b]pyridine (10.0 g, 95percent): H NMR (400 MHz, methanol-d4) δ 8.46 (s, 1H), 8.40 (s, 1H), 8.21 (s, 1H). |
86.7% | at 90℃; for 3 h; | Step 1: A solution of 5-bromo-pyridine-2,3-diamine (3.0 g, 15.96 mmol) and HCOOH (1.1 mL) in triethoxymethane(48 mL) was stirred at 90 °C for 3 h. The reaction mixture was concentrated under reduced pressure. The residuewas purified by silica gel chromatography eluting with 40:1 DCM/MeOH to give 6-bromo- 3H-imidazo[4,5-b]pyridine asa light brown solid (2.74 g, 86.7percent). 1H NMR (300 MHz, DMSO-d6) δ 8.49 (s, 1H), 8.44 (s, 1H), 8.30 (br s, 1H). LCMS(ESI) m/z 198 (M + H)+. |
51% | at 20℃; Heating / reflux | Example 8; 6-(Tributylstannyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazo[4,5-b]pyridine 5046 47[00248] To 3.07 g of 5-bromo-2,3-diaminopyridine 46 was added 20 mL formic acid under N2 and the reaction was heated to reflux for four hours and allowed to cool to room temperature. The reaction was stirred overnight at room temperature and complete reaction was confirmed by LCMS. The solution was concentrated in vacuo and purified by flash chromatography (DCMTMeOH) to give 1.64 g of compound 47 (51percent yield). |
51% | for 4 h; Heating / reflux | Example 6a 6-(Tributylstannyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazo[4,5-b]pyridine 50[00289] To 3.07g of 5-bromo-233-diaminopyridine was added 20 mL formic acid under N2 and the reaction was heated to reflux for four hours and allowed to cool to room temperature. The reaction was stirred overnight at room temperature and complete reaction was confirmed by LCMS. The solution was concentrated in vacuo and purified by flash chromatography (DCM/MeOH) to give 1.64g of compound 47 (51percent yield). Compound 47 (1.64g) in 40 mL THF was added to 0.22g (1.1 eq) NaH in 10 mL THF under N2 at -78° C. The reaction was stirred at -78° C for 30 minutes followed by the addition of 1.45g of SEM- Cl (1.05eq) and allowed to warm up to room temperature. The reaction was stirred at room temperature overnight and complete reaction was confirmed by LCMS. The reaction was quenched with water followed by the addition of NaCl (not saturated) and the two products <n="142"/>extracted with EtOAc and concentrated in vacuo. The two regioisomers were separated by flash chromatography (EtOAc/Hexanes) to give 1.68 g 48 and 0.5g 49 (80percent overall yield). Compound 49 (0.5g) was dissolved in 50 mL dioxane followed by the addition of 1.76 g (2.0eq) of Bis (tributyltin), 88 mg (0.05eq) of Pd(PPh3)4, and 0.19g (3.0 eq) of LiCl. The reaction mixture was heated to reflux under N2 for 1.5 hours and complete reaction confirmed by LCMS. The mixture was cooled to room temperature, filtered through celite (celite washed with EtOAc)5 rotovapped and purified by flash chromatography (EtOAc/Hexanes) to give 501 mg of 6-(Mbutylstoennyl)-l-((2-(trimemylsilyl)ethoxy)methyl)-lH-imidazo[4,5- b]pyridine 50 (61percent yield). MS (Ql) 539.2 (M) + |
1 g | at 100℃; for 3 h; | To a stirred solution of 5-Bromo-pyridine-2,3-diamine (2g, 10.6mmol ) in triethyl orthoformate ( 10 ml) was added formic acid( 1 ml ) and the total reaction mass stirred at 100°C for 3h.Reaction mass was cooled to room temperature and concentrated under vacuum. Crude reaction mass was purified by eluting with 5percent methanol in dichloromethane to get the desired compound 2 (lg ) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 g | at 100℃; for 3 h; | Step-1 [0138] To a stirred solution of 5-Bromo-pyridine-2,3-diamine (2 g, 10.6 mmol) in triethyl orthoformate (10 ml) was added formic acid (1 ml) and the total reaction mass stirred at 100° C. for 3 h. Reaction mass was cooled to room temperature and concentrated under vacuum. Crude reaction mass was purified by eluting with 5percent methanol in dichloromethane to get the desired compound 2 (1 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
620 mg | for 4 h; Reflux | General procedure: A mixture of 2,3-diaminopyridine in diethyl oxalate (10 mL/1 mmol phenyldiamine) was heated to reflux for 4 h before cooled to room temperature. The resulted solid was filtered,washed with ethyl acetate and 95percent ethanol, decolorized with activated charcoal and recrystallized in water and DMF or DMSO to give 5-azaquinoxalinediones as white solid. 5.2.2.15 7-Bromo-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (15) The title compound was prepared from 2-amino-5-bromopyridine according to the general procedure as white solid (620 mg, 25.6percent). IR (KBr) ν 3199, 3138, 3045, 2751, 1715, 1603, 1446, 1389 cm-1; 1H NMR (400 MHz, DMSO-d6) δ 7.55 (1H, d, J = 1.6 Hz, H-6), 8.15 (1H, d, J = 1.6 Hz, H-8); 13C NMR (100 MHz, DMSO-d6) δ 112.36, 123.20, 123.80, 138.46, 141.83, 154.55, 155.58; HRMS-EI C7H4BrN3O2 calcd [M+H]+ 241.9565, found 241.9567. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: With hydrogenchloride In 1,4-dioxane; water for 0.5 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 14 h; Heating / reflux |
To a soln of [BROMOACETALDEHYDE] diethyl acetal (2.37 mL, 15.4 [MMOL)] in [DIOXANE/H20] (2: 1/15 mL) at rt was added conc. [HCI] (0.3 mL) and the mixture was refluxed for 30 min. The mixture was cooled to rt whereupon [NAHCO3] (2.6 g, 30.8 [MMOL)] was carefully added followed by dropwise addition of diamino derivative (1.5 g, 7.7 [MMOL)] in [DIOXANE/H20] (2: [1/15] mL). The resultant mixture was stirred at reflux for 14 h and was cooled to rt. The mixture was diluted with 1 M [NAOH] (30 mL) and was extracted with [CH2CI2] (3 x 35 mL). The organic layers were combined, washed with brine [(1] x 20 mL), dried [(NA2SO4),] filtered and concentrated under reduced pressure to afford 1.5 g (92percent) of the desired compound [[M +] H = 214. [0].] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium hydrogencarbonate In ethanol; water for 17 h; Reflux | [0264] To a stuffed solution of compound I (50 g; 0.26 mol; 1 eq) in ethanol (2 L) was added sodium bicarbonate (46 g; 0.53 mol; 2 eq) and chloroacetaldehyde solution (—50percent aqueous solution, 86 mL; 0.66 mol; 2.5 eq) drop wise and the resulting mixture was heated at reflux for 17 h. The mixture was then evaporated to dryness and the pH was adjusted to 7 using ice-cold saturated aqueous NaHCO3 solution and solid NaHCO3. The organic components were extracted from the aqueous layer with ethyl acetate (3 x 1000 mL) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to obtain a dry residue which was purified by silica gel (230-400 mesh) column chromatography using 10-50percent ethyl acetate/hexanes as the eluent to afford the title compound (40 g, 71percent) as a brown solid. 1H NMR (DMSO-d6) ö 8.04 (s, 1H), 7.77 (s, 1H), 7.44 (s, 1H), 6.31 (s, 1H), 5.99 (s, 2H). LCMS: m/z = 212.0 [M+j, 214.0 [M+21, RT = 2.55 minutes, (Program P1, Column V). |
40% | at 20℃; Reflux; Inert atmosphere | To a stirred solution of 5-bromopyridine-2,3-diamine (278 g, 1478 mmol) in isopropanol (2.2 L) at rt was added chloroacetaldehyde (255 g, 1626 mmol) in one portion. After stirring in an nitrogen atmosphere under reflux overnight, the mixture was stirred for an additional 60 min at rt. The suspension was filtered, and the remaining solid was washed with isopropanol and dried in vaccuo at 50° C. Redissolution in methanol and evaporation yielded 6-bromoimidazo[1,2-a]pyridin-8-amine as a brown solid (124 g, 40 3/4): 1H-NMR (300 MHz, d6-DMSO): δ =8.39 (2H), 8.12 (2H), 6.92 (1H) ppm. |
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