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CAS No. : | 884495-39-0 | MDL No. : | MFCD07368887 |
Formula : | C6H7BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HJOOFLFWIISCAI-UHFFFAOYSA-N |
M.W : | 203.04 | Pubchem ID : | 44754869 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.83 |
TPSA : | 48.14 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) : | -6.71 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | 1.17 |
Log Po/w (WLOGP) : | 1.44 |
Log Po/w (MLOGP) : | 0.72 |
Log Po/w (SILICOS-IT) : | 1.31 |
Consensus Log Po/w : | 1.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.21 |
Solubility : | 1.24 mg/ml ; 0.00611 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.78 |
Solubility : | 3.4 mg/ml ; 0.0167 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.65 |
Solubility : | 0.453 mg/ml ; 0.00223 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H317-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 potassium acetate In 1,4-dioxane at 20 - 100℃; | Step A2-methoxy-5-(4, 4, 5, 5-tetra rolan-2-yl)pyridin-3-amine[00403] A degassed mixture of 5-bromo-2-methoxypyridin-3-amine (2 g, 9.85 mmol), 4i4,4',4,,5,5,5',5'-octamethyl-2,2'-bi-1 ,3,2-dioxaborolane (3.00 g, 11.82 mmol), Pd(dppf)2CI2 CH2CI2 adduct (0.804 g, 0.985 mmol) and potassium acetate (3.87 g, 39.4 mmol) in 1 ,4-dioxane (50 mL) was heated at 100 °C for 18 h, then stirred at room temperature over the weekend. The resulting mixture was filtered through pad of Celite.(R). with the aid of EtOAc. The filtrate was concentrated and reevaporated from CH2CI2/hexane. The residue was dissolved in CH2CI2 and purified by column chromatography (silica gel, 0-100percent EtOAc/hexane) to obtain 2-methoxy-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-amine (3.9 g, 9.36 mmol, 95 percent yield) as a light brown solid: H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 12 H) 3.87 (s, 3 H) 4.92 (s, 2 H) 7.12 (d, J=1.46 Hz, 1 H) 7.63 (d, J=1.37 Hz, 1 H); ES LC-MS m/z =251.4 (M+H)+. |
91.1% | Stage #1: for 0.166667 h; Inert atmosphere Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere |
Using similar reaction conditions as described in step ii of intermediate-3 , 5-bromo-2-methoxypyridin-3-amine (891mg, 4.39 mmol) was coupled with 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.86g, 5.27mmol) using potassium acetate(1.46g, 14.92 mmol)and PdClz(dppf) (160mg, 0.21mmol) in 1,4-dioxane (30mL) to give 1g (91.1percent yield) of the25 pure product after purification by chromatographic column (Silicagel-601120) using 20percentethyl acetate as eluent. |
55% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 2 h; Inert atmosphere | General procedure: 5-Bromo-2-methoxypyridin-3-amine (1.73 g, 6.82 mmol) was dissolved in 50 mL dioxane. Bis(pinacolato)diboron (4.4 g, 17.33 mmol), potassium acetate (2.5 g, 25.47 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Finally, bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.9 g, 0.16 mmol) was added under argon conditions. The mixture was then heated at 80°C for 2h. The crude was partitioned between ethyl acetate and water and then filtered through a plug of celite. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1 Purification System (0percent to 20percent, hexane-ethyl acetate) to obtain 1.43g. This solid was triturated with hexane, filtered and dried in the oven to give 0.94 g (55percent yield) of the desired product as a solid. Purity 100percent. LRMS (m/z): 251 (M+1 )+ |
55% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 2 h; Inert atmosphere | 5-Bromo-2-methoxypyridin-3-amine (1 .73 g, 6.82 mmol) was dissolved in 50 mL dioxane. Bis(pinacolato)diboron (4.4 g, 17.33 mmol) and potassium acetate (2.5 g, 25.47 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Then bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.9 g, 0.16 mmol) was added under argon conditions and the mixture heated at 80°C for 2h. The reaction mixture was partitioned between ethyl acetate and water and filtered through a plug of celite. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1®Purification System (0percent to 20percent, hexane-ethyl acetate) to obtain 1 .43g. This solid was triturated with hexane, filtered and dried in the vacuum oven to give 0.94 g (55percent yield) of the desired product as a solid. Purity 100percent.LRMS (m/z): 251 (M+1 )+. |
39% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 16 h; Inert atmosphere | 5-Bromo-2-methoxypyridin-3-amine (2.0 g, 9.85 mmol, 1 equivalent) was added to dioxane followed by bis(pinacolato)diboron (5.0 g, 19.7 mmol, 2 equivalents), potassium acetate (2.9 g, 29.6 mmol, 3 equivalents) and (1,1’-bis(diphenyl-phosphosphinol)ferrocene)dichloropalladium(II) dichloromethane adduct (0.804 g, 0.985 mmol, 0.1 equivalents) and stirred at 80 °C for 16 hours under argon. After cooling the solution was diluted with water and the product extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated. The product was then purified by column chromotography (DCM:EtOAc 1:1) and concentrated. The residue was triturated with diethyl ether to give the product as a yellow solid (950 mg, 39percent). |
4.05 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | 2-(Methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine To 5-bromo-2-(methyloxy)-3-pyridinamine (18.93 g, 93 mmol, available from Asymchem) in a 1 L round-bottom flask was added nitrogen-purged 1,4-Dioxane (500 mL) followed by 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (47.4 g, 186 mmol), potassium acetate (27.5 g, 280 mmol) (0.402 g, 0.493 mmol) and PdCl2(dppf)-CH2Cl2 adduct (7.61 g, 9.32 mmol). The mixture was then stirred at 80° C. under nitrogen. The reaction mixture was allowed to cool then partitioned between ethyl acetate and water. The mixture was filtered through a celite pad and the aqueous layer extracted further with ethyl acetate (2*). The combined organics were washed with water, brine and dried over magnesium sulphate overnight. The residue was purified on 1.5 Kg Silica cartridge, eluting a 0-50percent ethyl acetate/dichloromethane over 10 column volumes. The appropriate fractions were combined and evaporated to dryness. The residue was triturated with cyclohexane, the solid filtered off and dried in vacuo to leave the title compound as a light pink solid (1.1 g). LCMS (Method A) Rt 0.91 mins, MH+ 251A second crop was obtained from the above filtrate andafier drying gave a thrther portion of the title compound as alight pink solid (2.95 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With iron; ammonium chloride In ethanol; water for 15 h; Reflux | To a suspension of 5-bromo-2-methoxy-3-nitropyridine (9.62 g, 41.3 mmol) in ethanol (100 mL) and water (10 mL) was added Iron powder (9.25 g, 165.2 mmol, Tianjin guangfukeji) and NH4Cl (8.83 g, 165.2 mmol). The mixture was heated to reflux and stirred further for 15 hours, then cooled to rt, and concentrated in vacuo. The residue was dissolved in 250 mL of EtOAc and the resulted solution was washed with saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL*2) and brine (150 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a yellow solid (8.16 g, 97percent). MS (ESI, pos. ion) m/z: 202.8 [M+H]+. |
95% | With water; iron; ammonium chloride In ethanol at 95℃; for 1 h; | 5- Bromo-2-methoxypyridin-3-amine (16); [00198] In a 500 mL, round-bottomed, single-necked flask equipped with a magnetic stirring bar was placed 5-bromo-2-methoxy-3-nitropyridine (15) (20.0 g, 0.086 mol), Fe (20.0 g, 0.36 mol), and NH4Cl (20.0 g, 0.36 mol) in EtOH/H2O (150 mL, 1:1). After heating at 95 0C for 1 h, the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated to give 16.5 g (95 percent) of 5- bromo-2- <n="76"/>methoxypyridin-3-amine (16) as a solid. |
86% | With iron; ammonium chloride In ethanol; water for 1 h; Reflux | To a suspension of 5-bromo-2-methoxy-3-nitropyridine (0.4 g, 1.72 mmol) in EtOH(5 mL) and H20 (5 mL) was added iron powder (0.38 g, 6.87 mmol) and NH4Cl (0.39 g, 7.21mmol). The reaction refluxed for 1 h, then cooled down to rt and concentrated in vacuo. Theresidue was diluted with EtOAc (1 0 mL) and the resulted mixture was filtered through a pad ofcelite. The filtrate was extracted with EtOAc (10 mL x 3) and the combined organic phases werewashed with brine (10 mL), dried over anhydrous Na2S04 and concentrated in vacuo to give thetitle compound as a yellow solid (0.3 g, 86percent). The title compound was characterized byLC-MS and 1H NMR as shown below:LC-MS (ESI, pos. ion) m/z: 203 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 3.92 (s, 3H), 4.86 (s, 2H), 7.03 (d, J = 2.0 Hz, 1H), 7.41 (d,J = 2.0 Hz, 1H). |
86% | With ethanol; iron; ammonium chloride In water for 1 h; Reflux | To a suspension of 5-bromo-2-methoxy-3-nitropyridine (0.4 g, 1.72 mmol) in EtOH (5 mL) and H2O (5 mL) were added iron powder (0.38 g, 6.87 mmol) and NH4Cl (0.39 g, 7.21 mmol). The reaction was heated to reflux and stirred further for 1 hour, and then concentrated in vacuo. The residue was diluted with EtOAc (10 mL) and the resulted mixture was filtered through a pad of CELITE®. The filtrate was extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (0.30 g, 86percent). [0301] MS (ESI, pos. ion) m/z: 203.0 [M+H]+; [0302] 1H NMR (400 MHz, CDCl3) δ (ppm): 3.92 (s, 3H), 4.86 (s, 2H), 7.03 (d, J=2.0 Hz, 1H), 7.41 (d, J=2.0 Hz, 1H). |
86% | With iron; ammonium chloride In ethanol; water for 1 h; Reflux | The 5-bromo-2-methoxy-3-nitro pyridine (0.4g, 1 . 72mmol) suspended in EtOH (5 ml) and H 2 O (5 ml) in the mixed solution, adding Fe powder (0.38g, 6 . 87mmol) and NH 4 Cl (0.39g, 7 . 21mmol). Reaction liquid heating reflux for 1 hour, cooling to room temperature, and concentrating under reduced pressure. For residual EtOAc (10 ml) dilution, diatomite filter for the resulting mixture. Filtrate using EtOAc (10mLx3) extraction, the organic phase of the first combined and salt water (10 ml) to wash, anhydrous Na 2 SO 4 drying, and concentrating under reduced pressure, to obtain the title compound as yellow solid (0.3g, 86 |
81% | Stage #1: With tin(ll) chloride In ethyl acetate for 3 h; Heating / reflux Stage #2: With sodium hydroxide In dichloromethane; water; ethyl acetate at 0℃; for 2 h; |
b) 5 -bromo-2-(methyloxy)-3 -pyridinamine. To a solution of 5 -bromo-2-(methyloxy)-3 -nitropyridine (82 mmol) in ethyl acetate (300 mL) was added tin(II)chloride dihydrate (328 mmol). The reaction mixture was stirred for 3 h at reflux. (Caution: during the initial exotherm, that subsided after ~10 min, the heating bath was temporarily removed.) After cooling to room temperature, the mixture was concentrated under vacuum to a pale yellow slurry. The slurry was poured into 6 N aq. sodium hyroxide (300 mL), ice water (300 mL), and dichloromethane (300 niL) and stirred for 2 h until mostly dissolved. The small amount of insoluble material was filtered off and the organic phase was separated, dried over sodium sulfate, filtered, and evaporated to dryness. The resultant brown oil was triturated with hexanes to obtain a solid, which was filtered and dried in vacuo to afford the title product (81percent) as a pale green solid. MS(ES)+ m/e 202.8 [M+H]+. |
81% | Stage #1: With tin(ll) chloride In ethyl acetate for 3 h; Heating / reflux Stage #2: With sodium hydroxide; water In dichloromethane at 0℃; for 2 h; |
3 - Amino-5 -bromo-2-methoxypyridineTo 5 -Bromo-2-methoxy-3 -nitropyridine (19.0 g, 82 mmol) in EtOAc (300 mL) was added Tin(II)chloride dihydrate (74 g, 328 mmol). The reaction was stirred and refluxed for 3 h. (During the initial exotherm, that subsided after ~10 minutes, the heating bath was temporarily removed.) After cooling to RT the reaction was concentrated under vacuum to a pale yellow slurry. The slurry was poured into aq. 6 N NaOH (300 mL), ice (300 mL) and CH2CI2 (300 mL) and stirred for 2 h till mostly dissolved. The small amount of insoluble material was filtered off, the organic phase separated, dried (Na2SO4), filtered and evaporated to dryness. Trituration with hexanes solidified the brown oil which remained. Filtration and drying under vacuum gave the title product (13.40 g, 81percent) as a pale green solid: MS(ES)+ m/e 202.8 [M+H]+. |
77% | With tin(II) chloride dihdyrate In acetic anhydride for 3 h; Reflux | Step D 5-bromo-2-methoxypyridin-3-amine[00298] Tin (II) chloride dihydrate (87 g, 386.2 mmol) was added into a solution of 5- bromo-2-methoxy-3-nitropyridine (18 g, 72.2 mmol) in acetyl acetae (450 mL) at r.t. and the resulting mixture was refluxed for 3 hours with TLC monitoring. After the full conversion of starting material, the reaction mixture was cooled to r.t. and slowly poured into 6 N NaOH (500 mL) and stirred for a period of 10 minutes. The precipitate was filtered out with suction, and the filtrate was extracted with EtOAc (500 mL x 3). The combined organic layer was dried over Na2S04, filtered, and concentrated to dry to give a residue which was purified with column chromatography (EtOAc: petroleum ether = 1 : 4 as eluent) to give the product as a white solid (12 g, 77percent). LC/MS, ESI, m/z, 203, 205 (m+1 )+, Br pattern found. |
76% | With tin(II) chloride dihdyrate In ethyl acetate for 4 h; Reflux | To a solution of 16 (12.0 g, 51.7 mmol) in EtOAc (200 mL) was added SnCl2*2H2O (50.0 g, 221.6 mmol). The reaction mixture was stirred and heated at reflux for 4 h. After removal of the solvent, the residue was treated with 2 N aqueous NaOH and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (9:1 hexanes/EtOAc) to afford 17 (8.0 g, 76percent) as a pale yellow solid, mp 58-60 CH3. 1H NMR (CDCl3) δ 7.58 (d, J = 2.0 Hz, 1H, Ar-H), 6.98 (d, J = 2.0 Hz, 1H, Ar-H), 3.96 (s, 3H, OCH3). |
76% | With tin(II) chloride dihdyrate In ethyl acetate at 50℃; for 3 h; Inert atmosphere | 4.1.2 5-Bromo-2-methoxypyridin-3-amine (3) A mixture of 5-bromo-2-methoxy-3-nitropyridine (2) (5.0 g, 21.55 mmol) and tin(II) chloride dihydrate (24.35 g, 107.75 mmol) was dissolved into ethyl acetate (0.2 L) and stirred at 50 °C for 3 h under a nitrogen atmosphere. The mixture was dissolved in EtOAc (0.8 L), washed with 1 N sodium hydroxide (1.2 L) twice, water twice, dried over magnesium sulfate and concentrated to give the title compound (3.31 g, 16.39 mmol, 76percent yield) as a brown solid. 1H NMR (500 MHz, DMSO-d6) δ 7.37 (d, J = 2.0 Hz, 1H, Ar-H), 6.97 (d, J = 2.0 Hz, 1H, Ar-H), 5.28 (s, 2H, NH2), 3.82 (s, 3H, OCH3). ESI-MS: m/z = 203 [M+H]+. |
75% | With stannous chloride dihydrate In ethyl acetate for 3 h; Reflux | A solution of 985 mg (4.23 mmol) C-4 in 10 mL EtOAc is treated with 3.82 g (16.9 mmol) tin-II-chloride dihydrate. The mixture is stirred under reflux for 3 h. After cooling to RT, the solvent is removed under reduced pressure and the crude product is taken up in 9.5 mL aqueous 2 N NaOH. After stirring at RT for 1 h, DCM is added and the mixture is filtered over Celite. The aqueous phase is extracted with DCM, the combined organic layers are dried over MgSO4 and the solvent is removed under reduced pressure. The crude product can be used without further purification. Yield: 647 mg (75percent). |
58.7% | Stage #1: With tin(ll) chloride In ethyl acetate for 6 h; Heating / reflux Stage #2: With sodium hydroxide In water at 20℃; for 1 h; |
b) 5-bromo-2-(methyloxy)-3-pyridinamine; To a solution of 5-bromo-2-(methyloxy)-3-nitropyridine (45 g, 193 mmol) in ethyl acetate (1 L) was added tin(II) chloride dihydrate (174 g, 772 mmol). The reaction mixture was heated at reflux for 4 h. LC/MS indicated some starting material remained, so added 20 molpercent tin (II) chloride dihydrate and continued to heat at reflux. After 2 h, the reaction was allowed to cool to ambient temperature and concentrated in vacuo. The residue was treated with 2 N sodium hydroxide and the mixture stirred for 1 h. The mixture was then with methylene chloride (1 L), filtered through Celite, and washed with methylene chloride (500 mL). The layers were separated and the organics dried over magnesium sulfate and concentrated to give 5-bromo-2-(methyloxy)-3-pyridinamine (23 g, 113 mmol, 58.7 percent yield). The product was used crude in subsequent reactions. MS(ES)+ m/e 201.9, 203.9 [M+H]+. |
58.7% | Stage #1: With tin(II) chloride dihdyrate In ethyl acetate for 6 h; Reflux Stage #2: at 20℃; for 1 h; |
b) 5-bromo-2-(methyloxy)-3-pyridinamine To a solution of 5-bromo-2-(methyloxy)-3-nitropyridine (45 g, 193 mmol) in ethyl acetate (1 L) was added tin(II) chloride dihydrate (174 g, 772 mmol). The reaction mixture was heated at reflux for 4 h. LC/MS indicated some starting material remained, so added 20 mol percent tin (II) chloride dihydrate and continued to heat at reflux. After 2 h, the reaction was allowed to cool to ambient temperature and concentrated in vacuo. The residue was treated with 2 N sodium hydroxide and the mixture stirred for 1 h. The mixture was then with methylene chloride (1 L), filtered through Celite, and washed with methylene chloride (500 mL). The layers were separated and the organics dried over magnesium sulfate and concentrated to give 5-bromo-2-(methyloxy)-3-pyridinamine (23 g, 113 mmol, 58.7percent yield). The product was used crude in subsequent reactions. MS(ES)+ m/e 201.9, 203.9 [M+H]+. |
1.13 kg | at 20 - 25℃; Large scale | 5-Bromo-2-(methyloxy)-3-pyridinamine Iron powder (1.17 kg) was added to a suspension of 5-bromo-2-(methyloxy)-3-nitropyridine (1.36 kg) in IMS (6.1 L), stirred under nitrogen at 20-25° C. Water (0.8 L) was then added and the mixture cooled to less than 10° C. Aqueous hydrochloric acid (0.8 L concentrated hydrochloric acid and 0.8 L water) was then added to the reaction mixture, maintaining the temperature below 10-15° C. The suspension was warmed to 20-25° C. and then stirred at this temperature for 23 hours. The suspension was filtered, the filter cake washed with IMS (2*2.7 L) and the combined filtrates concentrated under vacuum. Water (4.1 L) was added slowly to the concentrated solution and the resulting suspension was held at 20-25° C. for 1.75 hours. The resultant suspension was filtered, washed with water (2*6.8 L) and the solid dried under vacuum to give the title compound as an off-white solid (1.13 kg). LCMS (Method B): Rt 2.16 mi MH 204. |
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