Structure of 552331-00-7
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CAS No. : | 552331-00-7 |
Formula : | C5H5IN2 |
M.W : | 220.01 |
SMILES Code : | NC1=NC=CC(I)=C1 |
MDL No. : | MFCD09038163 |
InChI Key : | RSMQQONIFJLFAK-UHFFFAOYSA-N |
Pubchem ID : | 22607551 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.36 |
TPSA ? Topological Polar Surface Area: Calculated from | 38.91 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.52 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.85 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.28 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.3 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.29 |
Solubility | 1.12 mg/ml ; 0.00507 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.25 |
Solubility | 12.4 mg/ml ; 0.0562 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.62 |
Solubility | 0.524 mg/ml ; 0.00238 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.04 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.92 |
* 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 |
---|---|---|
With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 1h; | To an ice-cold solution of the product from Step A above (3.84 g, 12.0 mmol) in 25 mL of dichloromethane was added trifluoroacetic acid (12 mL) dropwise. The resultant solution was allowed to warm to room temperature and, after 1 h, the volatiles were removed under reduced pressure. The residue was dissolved in water (120 ML), and the solution was neutralized by portionwise addition of sodium bicarbonate. The mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous brine, dried over magnesium sulfate and concentrated to afford an off-white solid, which was triturated with hexanes to afford the title compound as a white powder. MS 221.1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred solution of the product from Step B above (220 mg, 1.00 mmol) in N, N-dimethylformamide (0.5 ML) was added N, N-dimethylformamide dimethyl acetal (0.37 ML, 2.60 mmol). The reaction mixture was heated to 130 C OVERNIGHT. AFTER cooling to room temperature, the volatiles were removed under reduced pressure to afford a red oil, which was dissolved in 2.0 mL of methanol and 0.162 ML of pyridine. The solution was cooled in an ice bath and hydroxylamine-O-sulfonic acid (147 mg, 1.30 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The volatiles were removed under reduced pressure, and the residue was partitioned between saturated aqueous brine solution and ethyl acetate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous brine solution (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as an orange solid. MS 246.1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In tetrahydrofuran; | Example 75B N,N-Bis(tert-butyloxylcarbonyl)amino-4-iodopyridine A solution of the product from Example 75A above (1.0 g, 4.5 mmol) in THF (25 mL) was treated dropwise with 1.0M LiHMDS (9.0 mL, 9.0 mmol), stirred for 30 minutes, treated with di-t-butyl dicarbonate(1.96 g, 9.0 mmol) and stirred for 1 hour. The mixture was quenched with water (10 mL), warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 1:1 hexanes/ethyl acetate to provide the desired product (1.0 g, 53%). MS (DCI/NH3) m/z 421 (M+H). |
53% | Example 75B N,N-Bis(tert-butyloxylcarbonyl)amino-4-iodopyridine A solution of the product from Example 75A above (1.0 g, 4.5 mmol) in THF (25 mL) was treated dropwise with 1.0M LiHMDS (9.0 mL, 9.0 mmol), stirred for 30 minutes, treated with di-t-butyl dicarbonate(1.96 g, 9.0 mmol) and stirred for 1 hour. The mixture was quenched with water (10 mL), warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 1:1 hexanes/ethyl acetate to provide the desired product (1.0 g, 53%). MS (DCI/NH3) m/z 421 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium carbonate; In ethyl acetate; | Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonium hydroxide; In dimethyl sulfoxide; at 100℃; for 40h; | A mixture of 2-fluoro-4-iodopyridine (10.00g, 43.50mmol), ammonium hydroxide (10mL) in DMSO (20mL) was stirred at 100 C for 40 hours. H2O (100mL) was added to the reaction mixture and the precipitate was filtered to afford the compound 10a as a brown solid (8.62g, 90%). MS: 221 (M+H) +. |
90% | With ammonium hydroxide; In dimethyl sulfoxide; at 100℃; for 40h; | A solution of 2-fluoro-4-iodopyridine (10.00 g, 43.50 mmol) and ammonia (10 mL) in DMSO (20 mL) was stirred at 100 C for 40 h.Water (100 mL) was added to the reaction solution, and a solid was precipitated. The brown solid compound 10a (8.62 g, 90%) was obtained by filtration |
60% | With ammonia; In water; at 150℃; for 3h;Sealed tube; | Reference Example 2; 4-iodopyridin-2-amine2-Fluoro-4-iodopyridine (11.2 g, 50 mmol) obtained in Reference Example 1 and 28% aqueous ammonia solution (100 ml) were stirred at 150 C. for 3 hr in a sealed tube. The mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (6.6 g, yield 60%). melting point 167-168 C.1H-NMR (CDCl3) delta: 4.34 (2H, brs), 6.92 (1H, d, J=1.4 Hz), 6.99 (1H, dd, J=5.5, 1.4 Hz), 7.73 (1H, d, J=5.5 Hz). |
37% | With acetamide; potassium carbonate; In ethyl acetate; at 180℃; for 7h; | Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 14h;Inert atmosphere; | Example 20; bis(2,2,2-trichloroethyl)(4-(4-(4-methoxyphenyl)-2-oxopyrrolidin-1-yl)pyridin-2-yl)imidodicarbonateA solution of <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (440 mg, 2 mmol), 4-(4-methoxyphenyl)pyrrolidin-2-one (459 mg, 2.4 mmol) obtained in Reference Example 8, potassium phosphate (552 mg, 4 mmol), copper iodide (76 mg, 0.4 mmol) and N,N'-dimethylethylenediamine (43 mul, 0.4 mmol) in dioxane (10 ml) was stirred at 100 C. for 14 hr under an argon atmosphere. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue and triethylamine (0.35 ml, 4.8 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (0.6 ml, 4.4 mmol) at 0 C., and the mixture was stirred for 10 min. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (100 mg, yield 15%) as a solid.1H-NMR (CDCl3) delta: 2.75-2.87 (1H, m), 2.98-3.10 (1H. m), 3.65-3.77 (1H, m), 3.77-3.85 (1H, m), 3.82 (3H, s), 4.19 (1H, dd, J=9.3, 8.0 Hz), 4.79-4.83 (4H, m), 6.91 (1H, d, J=8.5 Hz), 7.19 (1H, d, J=8.5 Hz), 7.70 (1H, dd, J=5.8, 1.6 Hz), 7.73 (1H, d, J=1.6 Hz), 8.47 (1H, d, J=5.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 14h;Inert atmosphere; | Reference Example 3; 1-(2-aminopyridin-4-yl)pyrrolidin-2-oneA solution of <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (440 mg, 2 mmol) obtained in Reference Example 2, pyrrolidin-2-one (387 mg, 2.4 mmol), potassium carbonate (553 mg, 4 mmol), copper iodide (76 mg, 0.4 mmol) and N,N'-dimethylethylenediamine (43 mul, 0.4 mmol) in dioxane (10 ml) was stirred at 100 C. for 14 hr under an argon atmosphere. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from ethanol to give the title compound (160 mg, yield 45%).1H-NMR (CDCl3) delta: 2.17 (2H, tt, J=7.8, 6.9 Hz), 2.62 (2H, t, J=7.8 Hz), 3.82 (2H, t, J=6.9 Hz), 4.44 (2H, brs), 6.78 (1H, d, J=5.8, 1.9 Hz), 7.09 (1H, d, J=1.9 Hz), 8.01 (1H, d, J=5.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 10 - 35℃; for 16h;Reflux; Inert atmosphere; | Reference Example 42; 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-oneTo a solution of <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (2.0 g, 9.09 mmol), 5-phenyl-1,3-oxazolidin-2-one (1.7 g, 10.5 mmol) obtained in Reference Example 41 and potassium carbonate (2.5 g, 18.2 mmol) in 1,4-dioxane (30 mL) were added copper iodide (173 mg, 909 mumol) and N,N'-dimethylethylenediamine (80 mg, 909 mumol) at room temperature, and the mixture was heated under reflux for 16 hr under an argon stream. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.78 g, yield 77%) as crystals.melting point 155-156 C. (ethyl acetate-hexane)1H-NMR (CDCl3) delta: 3.90 (1H, dd, J=9.0, 7.5 Hz), 4.35 (1H, t, J=9.0 Hz), 4.49 (2H, br s), 5.64 (1H, t, J=7.5 Hz), 6.67 (1H, dd, J=6.0, 2.1 Hz), 6.93 (1H, d, J=2.1 Hz), 7.34-7.50 (5H, m), 8.00 (1H, d, J=6.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With copper(l) iodide; 1,10-Phenanthroline; at 130℃; for 23h; | A mixture of <strong>[552331-00-7]2-amino-4-iodopyridine</strong> (2.60 g, 11.8 mmol), copper (I) iodide (115 mg, 0.60 mmol), 1,10-phenanthroline monohydrate (120 mg, 0.60 mmol) and benzonitrile (33 mL) was heated in a 100 mL 4-necked flask to 130C. During 23 h a gentle flow of 02/N2 (5:95) was bubbled through the reaction mixture (99% conversion, HPLC method see below). The darkbrown suspension was then cooled to 0-5C and filtered. The filter cake was washed with TBME(10 mL) and dried to yield crude 7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.31 g, 61%) asa green solid with 100% purity (HPLC area-%, HPLC method see below). Charcoal treatment of the crude product with Norit SA 11(0.6 g) in EtOAc (100 mL) atreflux and subsequent crystallization (via partial evaporation of EtOAc) afforded 7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.82 g, 48%) as a white solid with 100% purity (HPLC area-%, method: Onyx Monolithic C18 column, 100 x 4.6 mm; mobile phase, A: water / NCMe (95:5), B: NCMe; flow: 2 ml/min; gradient from 95/5 (A/B) to 15/85 (A/B) within 3 mi isocratic 15/85 (A/B) for 2.5 mm, gradient 15/85 (A/B) to 95/5 (A/B) within 2 mm. Retention time: 2.77min( <strong>[552331-00-7]2-amino-4-iodopyridine</strong>), 3.51 mm (7-iodo-2-phenyl- [1,2,4] triazolo[ 1 ,5-a]pyridine)). EI-MS: mlz=321.98 (M+H)+. |
48% | With copper(l) iodide; 1,10-Phenanthroline; nitrogen; oxygen; at 130℃; for 23h; | A mixture of <strong>[552331-00-7]2-amino-4-iodopyridine</strong> (2.60 g, 11.8 mmol), copper (I) iodide (115 mg, 0.60 mmol), 1,10-phenanthroline monohydrate (120 mg, 0.60 mmol) and benzonitrile (33 mL) was heated in a 100 mL 4-necked flask to 130 C. During 23 h a gentle flow of O2/ N2 (5:95) was bubbled through the reaction mixture (99% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5 C. and filtered. The filter cake was washed with TBME (10 mL) and dried to yield crude 7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.31 g, 61%) as a green solid with 100% purity (HPLC area-%, HPLC method see below). [0076] Charcoal treatment of the crude product with Norit SA II (0.6 g) in EtOAc (100 mL) at reflux and subsequent crystallization (via partial evaporation of EtOAc) afforded 7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.82 g, 48%) as a white solid with 100% purity (HPLC area-%, method: Onyx Monolithic C18 column, 100×4.6 mm; mobile phase, A: water/NCMe (95:5), B: NCMe; flow: 2 ml/min; gradient from 95/5 (A/B) to 15/85 (A/B) within 3 min, isocratic 15/85 (A/B) for 2.5 min, gradient 15/85 (A/B) to 95/5 (A/B) within 2 min. Retention time: 2.77 min(<strong>[552331-00-7]2-amino-4-iodopyridine</strong>), 3.51 min (7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine)). [0077] EI-MS: m/z=321.98 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine; for 0.5h;Reflux; | A suspension of the product of Step A (4 g, 18.2 mmol) and anhydrous CuCN (1 .82 g, 20.3 mmol) in anhydrous pyridine (5 ml) was refluxed for 30 min. The solvent was removed in vacuo and the residue was partitioned between EtOAc (150 ml) and 10percent NH4CI (pH ~ 9, adjusted with NH40H; 50 ml). The organic phase was washed with brine, dried over anhydrous MgS04, filtered and the filtrate evaporated to dryness to give the title compound (1 .8 g, 82percent), as yellowish solid. 1 H NMR (CDCI3) 8.34 (d, 1 H, J = 2 Hz), 7.59 (dd, 1 H, J = 2, 8.7 Hz), 6.48 (dd, 1 H, J = 0.6, 8.6 Hz), 4.98 (broad s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium periodate; sulfuric acid; iodine; acetic acid; In water; at 20 - 80℃; for 4h; | 2-Aminopyridine (4.7 g,50 mmol) was dissolved in a mixture of water (6 mL),glacial acetic acid (120 mL), and concentrated sulfuricacid (1 mL) preliminarily cooled to room temperature. Upon mixing, iodine (6 g, 23.6 mmol) and NaIO4(1.6 g, 7.5 mmol) were added. The mixture was kept at80C for 4 h, then 200 mL of 10% sodium thiosulfate solution was added and extracted with ethyl acetate(3 × 150 mL). The organic phase was washed with10% sodium hydroxide solution (3 × 60 mL) and brine(2 × 50 mL), dried over anhydrous Na2SO4, evaporated,and purified by flash chromatography (chloroform-ethanol, 50 : 1). Violet powder (10.3 g, 94%);1H NMR: 8.04 (d, J2 2.1, 1H), 7.58 (dd, J2 8.6, 2.2,1H), 6.35 (d, J2 8.6, 1H), 6.10 (br, 2H). |
63% | With sodium periodate; sulfuric acid; iodine; acetic acid; In water; at 80℃; for 4h; | A mixture of 2-aminopyridine (2.4 g, 25 mmol), Nal04 (0.8 g, 3.75 mmol), and l2 (2.7 g, 10.7 mmol) in a pre mixed solution of AcOH (60 ml), H20 (3 ml) and concentrated H2S04 (0.5 ml) was stirred for 4 h at 80C. This was poured onto 10% Na2S203 (100 ml) and and resulting solution was extracted with EtOAc (3 x 50 ml). The organic phase was washed with 10% NaOH solution (3 x 30 ml), brine, dired over anhydrous MgS04, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by crystallization from EtOH to give the title compound (3.5 g, 63%), as yellowish solid. 1 H NMR (CDCI3) 10.5 (broad s, 2 H), 8.05 (d, 1 H, J = 2 Hz), 7.62 (dd, 1 H, J = 2, 8.8 Hz) ; 6.34 (d, 1 H, J = 8.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With pyridine; tetramethyl ammoniumhydroxide; at 80℃; for 1h; | General procedure: A solution of nitrosobenzene (1.3 mmol, 1.3 eq.) in pyridine (4 ml) was added dropwise into the mixture of tetramethylammonium hydroxide (25%w/w, 2 ml) and aminopyridine (1 mmol, 1 eq.) in pyridine (2 ml) over 60 min at 80 C. The solution was allowed to cool to room temp. and extracted with toluene (3 × 10 mL). The combined organic layers were washed with brine (10mL), dried (Na2SO4) and concentrated in vacuo. Flash column chromatography afforded the corresponding diazo-compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-dimethyl-aniline; In tetrahydrofuran; for 12h;Reflux; | [0097] The compounds A2, A3, A4, A5 and A11 from table A were prepared by the same method using the appropriate starting material. The compounds A6 and A9 from table A were prepared by the same method using the appropriate starting material and in these cases, A1 was isolated too as a by-product via halogen exchange. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In tetrahydrofuran; for 2h;Reflux; | To a solution of <strong>[552331-00-7]4-(iodo)pyridin-2-amine</strong> (463 mg, 2.0 mmol) in tetrahydrofurane (2.5 mL), in a sealed vial was added dihydro-2,5-furandione (1.5 equiv., 0.255 mg). The reaction mixture was reflux for 2 h. The mixture was allowed to cool down and a solide crystallize after one day. The solide was filtered and washed with diethyl ether to give the desired compound A13 in 58% yield. LC-MS (Method A) RT 0.66 (321 , M+H+, 319, M-H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In acetonitrile; at 70℃; for 2.5h;Inert atmosphere; | To a solution of (4-(3-ethynylimidazo[l,2-b]pyridazin-6-yl)phenyl)(4- methylpiperazin-l-yl)methanone (160 mg, 0.46 mmol) in acetonitrile (6 mL) under inert atmosphere was added <strong>[552331-00-7]4-iodopyridin-2-amine</strong> (132 mg, 0.60 mmol), Pd(PPh3)4 (26.6 mg, 0.02 mmol), Cul (8.8 mg, 0.05 mmol) and 3 mL of DIPEA. The reaction mixture was heated at 70 C for 2.5 h, was diluted with water (10 nlL) and extracted with dichloromethane (25 mL x 3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, eluent DCM/Methanol 94:6) and washed with saturated NaHC03 solution (5 mL x 2). The organic phase was dried over Na2S04, filtered and concentrated under reduced pressure and high vacuum to afford (4-(3-((2-aminopyridin-4- yl)ethynyl)imidazo[l,2-b]pyridazin-6-yl)phenyl)(4-methylpiperazin-l-yl)methanone (91.2 mg, 45%, AUC HPLC 99.08 %) as yellow solid mp: 120-122 C. 1H NMR (400 MHz, CDC13) delta (ppm): 8.20-8.00 (m, 5H), 7.70-7.50 (m, 3H), 6.85 (d, J = 4.8 Hz, 1H), 6.71 (s, 1H), 4.52 (bs, 2H), 3.84 (bs, 2H); 3.49 (bs, 2H), 2.60-2.30 (m, 4H), 2.21 (s, 3H); 13C NMR (400 MHz, CDC13) delta (ppm): 169.49, 158.41, 151.76, 148.31, 139.52, 139.20, 137.61, 136.40, 132.03, 127.88, 127.38, 126.12, 117.08, 115.73, 113.03, 110.05, 97.00, 79.26, 46.02; MS (ESI) m/z 438.20 [C25H23N70 + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.25h;Inert atmosphere; | Library Protocol 3 To a 0.2M solution of 5-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl)-2-[( 1 -[4-(trifluoromethoxy) phenyl]acetyl}piperidin-4-yl)oxy]benzamide (Preparation 14, 500 p L, 100 pmol) in DMF was added a 0.2M solution of compounds of formula (IV) (500 pL, lOOpmol) in DMF with argon purging. A 2M solution of cesium carbonate (100 pL, 200 pmol) in degassed water was added followed by tetrakis(triphenylphosphine)palladium (0) (5.7 mg, 5 pmol) and the reaction was heated to 130C under microwave irradiation for 15 minutes. The reaction wascooled and concentrated in vacuo. The residue was dissolved in DMSO (1 mL) and purified using preparative HPLC using one of the Purification Methods (PM) below: |
Tags: 552331-00-7 synthesis path| 552331-00-7 SDS| 552331-00-7 COA| 552331-00-7 purity| 552331-00-7 application| 552331-00-7 NMR| 552331-00-7 COA| 552331-00-7 structure
A431394 [1227581-81-8]
4-Iodo-5-methylpyridin-2-amine
Similarity: 0.83
A300612 [75073-11-9]
5-Iodo-6-methylpyridin-2-amine
Similarity: 0.74
A336198 [166266-19-9]
5-Iodo-3-methylpyridin-2-amine
Similarity: 0.72
A431394 [1227581-81-8]
4-Iodo-5-methylpyridin-2-amine
Similarity: 0.83
A300612 [75073-11-9]
5-Iodo-6-methylpyridin-2-amine
Similarity: 0.74
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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