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CAS No. : | 69214-09-1 | MDL No. : | MFCD08275698 |
Formula : | C7H5BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CCOFGVWHMYYDBG-UHFFFAOYSA-N |
M.W : | 197.03 | Pubchem ID : | 13037241 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.89 |
TPSA : | 17.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.52 cm/s |
Log Po/w (iLOGP) : | 1.91 |
Log Po/w (XLOGP3) : | 2.79 |
Log Po/w (WLOGP) : | 2.1 |
Log Po/w (MLOGP) : | 1.48 |
Log Po/w (SILICOS-IT) : | 1.67 |
Consensus Log Po/w : | 1.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.49 |
Solubility : | 0.0645 mg/ml ; 0.000327 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.81 |
Solubility : | 0.305 mg/ml ; 0.00155 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.94 |
Solubility : | 0.225 mg/ml ; 0.00114 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
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 |
---|---|---|
100% | With sodium hydrogencarbonate In ethyl acetate | PREPARATION 8; 5-Bromoimidazo [1, 2-a] pyridine Add 2-bromo-I, l-diethoxyethane (3.64 g, 18.48 mmol) to a solution of 6- bromopyridin-2-ylamine (l. Og, 5.77 mmol) in n-butanol (40 ml). Reflux overnight and cool. Filtration of the reaction mixture gives 1.3 g (81percent) of 5-bromoimidazo [1, 2- pyridine hydrobromide as a white solid. ESMS (M++1) : 198.9 m/z. Add saturated sodium bicarbonate (300 ml) to a suspension of 5- bromoimidazo [1, 2-a] pyridine hydrobromide (13. 0g, 46.96 mmol) in ethyl acetate. Separate the organic layer, wash with saturated sodium bicarbonate, dry over magnesium sulfate, and concentrate under reduced pressure to give 9.7 g (100percent) of the title compound as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | 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 for 24 h; Heating / reflux |
Method 32 5-Bromoimidazo[1,2a]pyridine A solution of bromoacetaldehyde diethylacetyl (50ml, 0.332mol) in dioxane (143ml), water (85ml) and conc. hydrochloric acid (5ml) was heated at reflux for 30 minutes and the mixture allowed to cool. Sodium hydrogen carbonate (53g) was added followed by a solution of 5-bromo-2-aminopyridine (30g, 0.174mol) in dioxane (230ml) and water (85ml) and the mixture was heated at reflux for 24 hours. The mixture was allowed to cool, poured into water and acidified with 2M hydrochloric acid. The mixture was washed with ethyl acetate and the aqueous layer was basified with 2M aqueous sodium hydroxide solution. The aqueous mixture was extracted with ethyl acetate. The extracts were combined, dried and the volatiles removed by evaporation. The residue was purified by chromatography eluding with hexane/ethyl acetate (50:50) in creasing in polarity to (25:50) to give the title compound 20g (59percent). NMR: 7.30 (dd, 1H), 7.54 (d, 1H), 7.59 (s, 1H), 7.90 (s, 1H), 8.89 (s, 1H); m/z: 197 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Method 33 3-Acetvl-5-bromoimidazo[1,2a]pyridine Aluminium chloride (10.2g, 77mmol) was added in portions over 10 minutes to a solution of 5-bromoimidazo[1,2a]pyridine (Method 32; 5.0g, 26mmol) in dichloromethane (100ml) cooled to 0C. The mixture was heated to reflux and acetyl chloride (2.54ml, 36mmol) was added over 15 minutes. The mixture was heated at reflux for 24 hours, cooled to 0C, and further aluminium chloride (10.2g, 77mmol) followed by acetyl chloride (3.26ml) were added. The mixture heated at reflux for 24 hours and then the volatiles were removed by evaporation. Iced water was added, the mixture was basified with 2M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extracts were washed with water, dried and the solvent evaporated to the title compound which was used without further purification 4.0g. NMR: 2.58 (s, 3H), 7.74-7.82 (m, 2H), 8.62 (s, 1H), 9.62 (s, 1H); m/z: 241 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydrogencarbonate; In ethyl acetate; | PREPARATION 8; 5-Bromoimidazo [1, 2-a] pyridine Add 2-bromo-I, l-diethoxyethane (3.64 g, 18.48 mmol) to a solution of 6- bromopyridin-2-ylamine (l. Og, 5.77 mmol) in n-butanol (40 ml). Reflux overnight and cool. Filtration of the reaction mixture gives 1.3 g (81%) of 5-bromoimidazo [1, 2- pyridine hydrobromide as a white solid. ESMS (M++1) : 198.9 m/z. Add saturated sodium bicarbonate (300 ml) to a suspension of 5- bromoimidazo [1, 2-a] pyridine hydrobromide (13. 0g, 46.96 mmol) in ethyl acetate. Separate the organic layer, wash with saturated sodium bicarbonate, dry over magnesium sulfate, and concentrate under reduced pressure to give 9.7 g (100%) of the title compound as a white solid. |
With sodium hydrogencarbonate; In water; ethyl acetate; | Add saturated sodium bicarbonate (300 ml) to a suspension of 5- bromoimidazo [1, 2-a] pyridine hydrobromide (13. 0g, 46.96 mmol) in ethyl acetate. Separate the organic layer and wash it with saturated sodium bicarbonate, dry over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; magnesium; In tetrahydrofuran; ethyl acetate; | (10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)-(imidazo[1,2-a]pyridin-5-yl)methanol To 40 ml of a tetrahydrofuran solution were added 1.20 g of magnesium and 0.1 ml of 1,2-dibromoethane in a nitrogen atmosphere. Subsequently, 10 ml of a solution of 2.96 g of <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> and 2.8 ml of 1,2-dibromoethane in tetrahydrofuran were dropped into the reaction mixture while heating under reflux. Further, 10 ml of a solution of 2.73 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)carbaldehyde in tetrahydrofuran was dropped thereinto. After heating to 50 C. for 1 hour, the reaction mixture was brought back to room temperature and distributed into an aqueous solution of ammonium chloride and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate followed by filtration. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 260 mg of the title compound as a yellow oily substance. 1H-NMR(CDCl3) delta ppm: 3.45(s, 3H), 3.60-3.85(br.s, 1H), 5.23(s, 2H), 5.74(s, 1H), 6.95(dd, J=1.4, 7.7 Hz, 1H), 6.99(d, J=7.7 Hz, 1H), 7.02(dd, J=1.7, 9.4 Hz, 1H), 7.19(d, J=1.4 Hz, 1H), 7.44(d, J=9.4 Hz, 1H), 7.52(s, 1H), 7.57(d, J=1.7 Hz, 1H), 7.83(d, J=2.6 Hz, 1H), 7.85(d, J=2.6 Hz, 1H), 8.14(s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.9% | With sodium hydrogencarbonate; triethylamine; In N-methyl-acetamide; ethyl acetate; | Reference Example 66 Synthesis of (imidazo[1,2-a]pyridin-5-ylthio ethyl acetate from <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> In a 50 mL-capacity reaction vessel, 103.2 mg of <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> was dissolved in 1 mL of dimethylformamide under argon atmosphere. To the reaction vessel was added 0.11 mL of triethylamine, to which was added 0.085 mL of thioglycolic acid ethyl ester. The mixture was stirred for 1.5 hour at room temperature, for 2 hours at 60 C. and for 9 hours at 80 C. The reaction mixture was left standing for cooling, to which were added a 1N-HCl aqueous solution (50 ml) and ethyl acetate (100 mL). The ethyl acetate layer was subjected to extraction with a 1N-HCl aqueous solution (50 mL*2). The acid aqueous solutions were combined, to which was added NaHCO3 for neutralization (pH 0.35-7.30). To the thus-neutralized solution was added ethyl acetate (50 mL*3) for extracting the product. The extract solutions were combined and dried over anhydrous magnesium sulfate, which was subjected to filtration. The filtrate was concentrated under reduced pressure to afford (imidazo[1,2-a]pyridin-5-ylthio) ethyl acetate as a black liquid product (150 mg, quantitative yield 56.9%, HPLC 79.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20g (59%) | Method 32 5-Bromoimidazo[1,2a]pyridine A solution of bromoacetaldehyde diethylacetyl (50ml, 0.332mol) in dioxane (143ml), water (85ml) and conc. hydrochloric acid (5ml) was heated at reflux for 30 minutes and the mixture allowed to cool. Sodium hydrogen carbonate (53g) was added followed by a solution of 5-bromo-2-aminopyridine (30g, 0.174mol) in dioxane (230ml) and water (85ml) and the mixture was heated at reflux for 24 hours. The mixture was allowed to cool, poured into water and acidified with 2M hydrochloric acid. The mixture was washed with ethyl acetate and the aqueous layer was basified with 2M aqueous sodium hydroxide solution. The aqueous mixture was extracted with ethyl acetate. The extracts were combined, dried and the volatiles removed by evaporation. The residue was purified by chromatography eluding with hexane/ethyl acetate (50:50) in creasing in polarity to (25:50) to give the title compound 20g (59%). NMR: 7.30 (dd, 1H), 7.54 (d, 1H), 7.59 (s, 1H), 7.90 (s, 1H), 8.89 (s, 1H); m/z: 197 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; isopropyl alcohol; at 80℃; for 15h; | To a solution of the compound of the previous step (2.3 g) in isopropanol (25 ml) were added <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> (1.1 g), 2.0M aqueous potassium carbonate solution (4.9 ml) and tetrakis(triphenylphosphine)palladium(0) (170 mg), and the mixture was stirred at 80C for 15 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=1:1?ethyl acetate) to give the title compound (1.8 g, 81%). NMR(300MHz, CDCl3)delta:1.42(3H, s), 1.47(3H, d, J=6.6Hz), 1.59(9H, s), 1.77(3H, br), 1.85-2.05(1H, m), 2.10-2.25(1H, m), 2.42-2.88(3H, m), 2.91-3.10(1H, m), 3.99(1H, q, J=6.6Hz), 6.69(1H, d, J=6.9Hz), 7.04-7.14(2H, m), 7.22-7.27(1H, m), 7.61(1H, d, J=1.2Hz), 7.64(1H, d, J=9.3Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With copper(I) thiophene-2-carboxylate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 140℃; for 0.333333h;Microwave irradiation; | A mixture of 2-[4-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2- J]pyrimidin-6-ylmethyl)piperazin-l-yl]isobutyramide (150 mg, 0.22 mmol), 5-bromo-7- methyl-imidazo[l,2-alpha]pyridine (55 mg, 0.26 mmol), Pd(PPh3)4 (25 mg, 0.02 mmol) and copper(I) thiophene-2-carboxylate (8 mg, 0.04 mmol) in dioxane (2 mL) was purged with argon gas then heated at 150 0C, for 20 min, in a microwave A mixture of 2- [4-(4-morpholin-4-yl-2-(tributylstannanyl)thieno [3,2- d]pyrimidin-6-ylmethyl)piperazin-l-yl]isobutyramide (0.35 g, 0.51 mmol), 5- bromoimidazo[l,2-alpha]pyridine (0.11 g, 0.56 mmol), copper(I) 2-thiophene carboxylate (0.019g, 0.1 mmol) and Pd(PPh3)4 (0.059 g, 0.05 mmol) in dioxane (5 mL) was subjected to microwave irradiation at 1400C for 20 min. The reaction mixture was loaded onto an Isolute SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH. The eluent was concentrated in vacuo and the residue was purified by flash chromatography (Si-PPC, MEOH:DCM, gradient 0:100 to 10:90). The residue was loaded onto an Isolute SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH. The solution was concentrated in vacuo and the residue was purified by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 75:25 to 2:98) to give 697 as a white powder (0.117 g, 45%). LCMS: Rx = 4.35min, [M+H]+ 521.2. 1H NMR (400 MHz, DMSO-d6): delta 9.33 (d, J = 1.1 Hz, 1 H); 8.04 (dd, J = 7.5, 1.2 Hz, 1 H); 7.78 (dd, J = 8.9, 1.1 Hz, 1 H); 7.74 (d, J = 1.2 Hz, 1 H); 7.54 (s, 1 H); 7.41 (dd, J = 8.9, 7.5 Hz, 1 H); 7.07 (d, J = 3.5 Hz, 1 H); 6.95 (d, J = 3.5 Hz, 1 H); 4.00 (t, J = 4.7 Hz, 4 H); 3.89 (s, 2 H); 3.82 (t, J = 4.7 Hz, 4 H); 2.56-2.54 (m, 4 H); 2.49-2.44 (m, 4 H); 1.08 (s, 6 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With copper(I) thiophene-2-carboxylate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 150℃; for 0.333333h;Microwave irradiation; Inert atmosphere; | A mixture of 2-[4-(7-methyl-4-morpholin-4-yl-2-(tributylstannanyl)thieno [3 ,2-d]pyrimidin-6-ylmethyl)piperazin- 1 -yljisobutyramide (150 mg, 0.21 mmol), 5-bromoimidazo[l,2-alpha]pyridine (50 mg, 0.25 mmol), Pd(PPh3)4 (24 mg, 0.02 mmol) and copper(I) thiophene-2-carboxylate (8 mg, 0.04 mmol) in dioxane (2 mL) was purged with argon gas then heated at 150 0C, for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute SCX-2 cartridge (10 g), washed with MeOH then eluted with 2 M NH3 in MeOH. The resulting residue was purified by flash chromatography (Si-PPC, MeOH:DCM, gradient 0:100 to 100:0) followed by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 95:5 to 2:98) to give 691 as a white solid (30 mg, 26%). LCMS (Method E) Rx 5.27 min; [M+H]+ 535. 1H NMR (400 MHz, CHCl3-d): delta 9.45 (s, 1 H); 8.09-8.05 (m, 1 H); 7.80-7.76 (m, 2 H); 7.32 (dd, J = 8.9, 7.19 Hz, 1 H); 7.10 (d, J = 5.3 Hz, 1 H); 5.20 (d, J = 5.3 Hz, 1 H); 4.07 (t, J = 4.7 Hz, 4 H); 3.91 (t, J = 4.7 Hz, 4 H); 3.84 (s, 2 H); 2.61 (m, 8 H); 2.51 (s, 3 H); 1.25 (s, 6 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(l) iodide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 140℃; for 0.333333h;Microwave irradiation; Inert atmosphere; | A mixture of dimethyl-[l-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2- <;i]pyrimidin-6-ylmethyl)piperidin-4-yl]amine (156 mg, 0.24 mmol), 5-bromoimidazo[l,2- alpha]pyridine (56 mg, 0.29 mmol), Pd(PPh3)4 (28 mg, 0.02 mmol) and copper(I) iodide (55 mg, 0.29 mmol) in THF (2.5 mL) was purged with argon gas then heated at 140 0C, for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute SCX-2 cartridge (5 g), washed with MeOH then eluted with 2 M NH3 in MeOH. The resulting residue was purified by flash chromatography (Si-PPC, MeOH:DCM, gradient 0:100 to 10:90) to give 688 as a white solid (72 mg, 63%). LCMS (Method F): Rx 3.89 min; [M+H]+ 478. 1H NMR (400 MHz, CHCls-d): delta 9.23 (s, 1 H); 7.95 (dd, J = 8.6, 1.3 Hz, 1 H); 7.77 (d, J = 8.6 Hz, 1 H); 7.75 (d, J = 1.3 Hz, 1 H); 7.35 (s, 1 H); 7.32-7.29 (m, 1 H); 4.07 (t, J = 4. 8 Hz, 4 H); 3.91 (t, J = 4.8 Hz, 4 H); 3.84 (s, 2 H); 3.04 (d, J = 11.25 Hz, 2 H); 2.33-2.25 (m, 6 H); 2.21-2.10 (m, 3 H); 1.84 (d, J = 12.5 Hz, 2 H); 1.61 (m, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With copper(l) iodide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 140℃; for 0.333333h;Microwave irradiation; Inert atmosphere; | A mixture of 4-morpholin-4-yl-6-(4-morpholin-4-ylpiperidin- 1 -ylmethyl)-2- (tributylstannanyl)thieno[3,2-(i]pyrimidine (69 mg, 0.10 mmol), 5-bromoimidazo[l,2- alpha]pyridine (24 mg, 0.12 mmol), Pd(PPh3)4 (11 mg, 0.01 mmol) and copper(I) iodide (23 mg, 0.12 mmol) in THF (1 mL) was purged with argon gas then heated at 140 0C, for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute SCX-2 cartridge (10 g). The cartridge was washed with MeOH then the product was eluted with 2 M NH3 in MeOH. The appropriate fractions were evaporated and the resulting residue was purified by flash chromatography (Si-PPC, MeOH:DCM, gradient 0:100 to 3:97) followed by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 70:30 to 2:98) to give 687 as a white solid (22 mg, 42%). LCMS (Method F): Rx 3.90 min; [M+H]+ 520. 1H NMR (400 MHz, CHCl3-d): delta 9.23 (s, 1 H); 7.95 (dd, J = 7.2, 1.2 Hz, 1 H); 7.77 (d, J = 8.9 Hz, 1 H); 7.75 (d, J = 1.2 Hz, 1 H); 7.35 (s, 1 H); 7.31 (dd, J = 8.9, 7.2 Hz, 1 H); 4.07 (t, J = 4.7 Hz, 4 H); 3.91 (t, J = 4.7 Hz, 4 H); 3.84 (s, 2 H); 3.74 (t, J = 4.4 Hz, 4 H); 3.05 (d, J = 11.4 Hz, 2 H); 2.57 (t, J = 4.4 Hz, 4 H); 2.29-2.19 (m, 1 H); 2.15 (t, J = 11.4 Hz, 2 H); 1.87 (d, J = 12.5 Hz, 2 H); 1.65-1.59 (m, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With copper(I) thiophene-2-carboxylate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation; Inert atmosphere; | A mixture of 2-[l-(5-imidazo[l,2-alpha]pyridin-5-yl-7-morpholin-4- ylthiazolo[5,4-(i]pyrimidin-2-ylmethyl)piperidin-4-yl]propan-2-ol (0.25 g, 0.37 mmol), 5- bromoimidazo[l,2-alpha]pyridine (0.082 g, 0.41 mmol), copper(I) 2-thiophene carboxylate (0.015g, 0.075 mmol) and Pd(PPh3)4 (0.044 g, 0.037 mmol) in dioxane (3 mL) was subjected to microwave irradiation at 1500C for 60 min. The reaction mixture was loaded onto an Isolute SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH. The eluent was concentrated in vacuo and the residue was purified by flash chromatography (Si-PPC, MEOH :DCM, gradient 0:100 to 90:10) followed by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 95:5 to 2:98) to give 699 as a yellow powder (0.052 g, 28%). LCMS (Method E): Rx = 4.38min, [M+H]+ 494.2. 1H NMR (CDCl3, 400MHz) delta 9.19 (s, 1 H); 7.99 (dd, J = 7.2, 1.3 Hz, 1 H); 7.81 (d, J = 8.9 Hz, 1 H); 7.76 (d, J = 1.3 Hz, 1 H); 7.33 (dd, J = 8.9, 7.2 Hz, 1 H); 4.48-4.35 (m, 4 H); 3.92-3.85 (m, 7 H); 3.10 (d, J = 11.2 Hz, 2 H); 2.23 (t, J = 11.2 Hz, 2 H); 1.83-1.77 (m, 2 H); 1.54-1.41 (m, 2 H); 1.38-1.29 (m, 1 H); 1.22 (s, 6 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With copper(I) thiophene-2-carboxylate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation; Inert atmosphere; | A mixture of 7-morpholin-4-yl-2-(3-morpholin-4-ylazetidin- 1 -ylmethyl)-5- (tributylstannanyl)thiazolo[5,4-(i]pyrimidine (0.25 g, 0.37 mmol), 5-bromoimidazo[l,2- alpha]pyridine (0.082 g, 0.41 mmol), copper(I) 2-thiophene carboxylate (0.015g, 0.075 mmol) and Pd(PPh3 )4 (0.044 g, 0.037 mmol) in dioxane (3 mL) was subjected to microwave irradiation at 150 0C for 60 min. The reaction mixture was loaded onto an Isolute SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH. The eluent was concentrated in vacuo and the residue was purified by flash chromatography (Si-PPC, MEOH:DCM, 0:100 to 10:90) followed by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 95:5 to 2:98) to give 700 as a yellow solid (0.101 g, 55%). LCMS (Method E): Rx = 3.98min, [M+H]+ 493.15. 1H NMR (CDCl3, 400MHz) 5 9.16 (s, 1 H); 7.98 (dd, J = 7.2, 1.2 Hz, 1 H); 7.81 (d, J = 8.9 Hz, 1 H); 7.76 (d, J = 1.2 Hz, 1 H); 7.33 (dd, J = 8.9, 7.2 Hz, 1 H); 4.47- 4.32 (m, 4 H); 4.04 (s, 2 H); 3.89 (t, J = 4.6 Hz, 4 H); 3.74 (t, J = 4.6 Hz, 4 H); 3.69 (t, J = 6.4 Hz, 2 H); 3.23-3.15 (m, 2 H); 3.14 (t, J = 6.4 Hz, 1 H); 2.40-2.36 (m, 4 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(I) thiophene-2-carboxylate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation; Inert atmosphere; | A mixture of 2-[ 1 -(9-methyl-6-morpholin-4-yl-2-(tributylstannanyl)-9H-purin- 8-ylmethyl)piperidin-4-yl]propan-2-ol (0.2 g, 0.30 mmol), 5-bromoimidazo[l,2-alpha]pyridine (0.066 g, 0.33 mmol), copper(I) 2-thiophene carboxylate (0.018g, 0.09 mmol) and Pd(PPh3)4 (0.052 g, 0.045 mmol) in dioxane (5 mL) was subjected to microwave irradiation at 1500C for 60 min. The reaction mixture was loaded onto an Isolute SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH. The eluent was concentrated in vacuo and the resultant residue was purified by flash chromatography (Si-PPC, MEOH:DCM, gradient 0:100 to 94:6) followed by reverse phase HPLC (Phenomenex Gemini 5u C 18, 20 mM triethylamine in water on a gradient of acetonitrile 95:5 to 2:98) to give 698 as a yellow powder (0.085 g, 58%). LCMS: Rx = 4.17min, [M+H]+ 491.2. 1H NMR (CDCl3, 400MHz) delta 9.26 (d, J = 1.2 Hz, 1 H); 7.96 (dd, J = 8.2, 1.2 Hz, 1 H); 7.76-7.73 (m, 2 H); 7.31 (dd, J = 8.2, 5.2 Hz, 1 H); 4.38 (t, J = 4.6 Hz, 4 H); 3.96 (s, 3 H); 3.89 (t, J = 4.6 Hz, 4 H); 3.75 (s, 2 H); 2.96 (d, J = 11.0 Hz, 2 H); 2.11 (t, J = 11.0 Hz, 2 H); 1.76 (d, J = 11.0 Hz, 2 H); 1.44-1.29 (m, 3 H); 1.18 (s, 6 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.4 mg | To a mixture of N-[3-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-y])phenyl]-2-[4- (ethylsulfonyl)phenyl]acetamide (intermediate 6b, 100 mg), 5-bromoimidazo[l,2-a]pyridine (51.0 mg) and sodium carbonate solution (2 M, 0.431 lnL) in DMF (3 mL) was added PdCl2(dppf)-CH2Cl2 adduct (8.80 mg) under nitrogen. The mixture was stirred and heated in the microwave at 100C for half an hour. After cooling, the mixture was diluted with water, and then extracted with EA for three times. The organic layer was dried and filtered through silica gel, evaporated in vacuo. The residue was purified by MDAP to afford N-(3-chloro-4-(imidazo[l,2-a]pyridin-5-yl)phenyl)-2-(4- (emylsulfonyl)phenyl)acetamide, trifluoroacetic acid salt (5.4 mg). 'H-NMR (400 MHz, DMSO-i/6) delta ppm 1.04 (t, J= 7.3 Hz, 3H), 3.23 (m, 2H), 3.83 (s, 2H), 7.34 (d, J= 7.0 Hz, 1H), 7.56 (m, 3H), 7.66 (m, 2H), 7.86 (m, 4H), 8.04 (s, 2H), 10.74 (s, 1H); 19F-NMR (376 MHz, DMSO- ) 6 ppm -73.70; MS(ES H/-: 454 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.3 mg | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 100℃; for 16h; | To a soulution of N-{4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl } -2-[4-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phen-oxy] acetamide(100 mg, 0.18 mmol) in anhydrous 1,4-dioxane (5 mL) were sequentially added <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> (32 mg, 0.16 mmol), PCy3 (1.2 mg, 0.0043 mmol), 1.27MK3P04 (0.22 ml, 0.27 mmol) and Pd2(dba)3 (1.4 mg, 0.00 16 mmol).The resulting mixturewas heated at 100 C for 16 hours. The reaction mixture was cooled to roomtemperature, filtered through celite and washed with methanol (100 mL). Evaporation of the filtrate and purification of the residue by preparative HPLC afforded N- {4-[(4- ethylpiperazin- 1 -yl)methyl] -3 -(trifluoromethyl)phenyl } -2-(4-imidazo[ 1 ,2-a]pyridin-5- yl}phenoxy)-acetamide (14.3 mg). ?H NMR (DMSO-d6) oe 10.46 (s, 1H), 8.09 (s, 1H),7.87-7.85 (m, 1H), 7.76 (s, 1H), 7.70-7.67 (m, 3H), 7.59-7.56 (m, 2H), 7.36-7.32 (m,1H), 7.22-7.20 (a, J = 8.7 Hz, 2H), 6.87-6.85 (d, J = 6.9 Hz, 1H), 4.84 (s, 2H),3.17-3.16 (d, J=4.9 Hz, 2H),2.38-2.27 (m, 1OH), 0.99-0.95 (t, J 6.9 Hz, 3H); ESI MS, m/z 538[M+Hf. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate; In 2-methyltetrahydrofuran; water; at 75℃; for 18h; | This reaction was carried out in two identical batches. A mixture of 5-(furo[3,2- c]pyridin-4-yloxy)-2-(4 ,4 ,5,5-tetram ethyl-i ,3,2-d ioxaborolan-2-yl)aniline (C26) (4.5 g, 13 mmol), potassium phosphate trihydrate (9.6 g, 36 mmol), [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (1.1 g, 1.3 mmol) and 5-bromoimidazo[i,2-a]pyridine (3.8 g, 19 mmol) in 2-methyltetrahydrofuran (50 mL) and water (10 mL) was heated to 75 00 for 18 hours. The two batches were cooled to room temperature and combined. After filtration, the filter cake was washed with water, and the combined filtrates were extracted with ethyl acetate (4 x 100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, andconcentrated in vacuo. The residue was combined with the filter cake and purified by silica gel chromatography (Gradient: 2% to 5% methanol in dichloromethane) to provide the product as a yellow solid. Yield: 4.2 g, 12 mmol, 46%. LOMS m/z 342.9 (M+H). 1H NMR (400 MHz, DMSOd 6) oe 8.14 (d, J=2.2 Hz, 1 H), 8.06 (d, J=5.9 Hz, 1 H), 7.60 (br d, J=9.0 Hz, 1 H), 7.58 (d, J=i .0 Hz, 1H), 7.50 (dd, J=5.9, 0.8 Hz, 1H), 7.33 (dd, J=9.0, 6.8 Hz, 1H), 7.32 (brs, 1H), 7.19 (d, J=8.2 Hz, 1H), 7.07 (dd, J=2.2, 0.9 Hz, 1H), 6.89 (brdd, J=6.8, 0.7 Hz, 1H), 6.65 (d, J=2.4 Hz, 1H), 6.50 (dd, J=8.4, 2.4 Hz, 1H), 5.17 (brs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h; | A mixture of 4,4,5,5-tetramethyl-2-(2-methyl-4-nitrophenyl)-1,3,2-dioxaborolane (390 mg, 1.48 mmol), <strong>[69214-09-1]5-bromoimidazo[1 ,2-a]pyridine</strong> (243 mg, 1 .23 mmcl), potassium carbonate (683mg, 4.94 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll)(90 mg, 0.12mmol) in N,N-dimethylformamide (10 mL) was stirred at 120 00 for 1 hour. The reaction mixture was filtered and the filtrate was concentrated in vacuo. Purification via silica gel chromatography (Eluent: 2% methanol in dichloromethane) afforded the product as a yellow oil. Yield: 320 mg,1.26 mmol, 100%. 1H NMR (400 MHz, ODd3) oe 8.27 (br s, 1 H), 8.22 (br d, J=8.5 Hz, 1 H), 7.73(d, J=9.0 Hz, 1H), 7.66 (brs, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.31 (dd, J=9.0, 7.0 Hz, 1H), 7.05 (s,1H), 6.75 (d, J=6.5 Hz, 1H), 2.23 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); lithium chloride; copper(I) bromide; In tetrahydrofuran; for 48h;Inert atmosphere; Reflux; | To a solution of 5-(furo[3,2-c]pyridin-4-yloxy)-2-(trimethylstannyl)benzonitrile (C76) (8.3 g, 21 mmol) in tetrahydrofuran (160 mL)was added <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> (3.9 g, 20 mmol), lithium chloride (0.67 g, 15.8 mmol), copper(l) bromide (0.57 g, 4.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.27 g, 2.0 mmol). The mixture was heated to reflux for 48 hours. The reaction mixture was filtered and the filtrate was concentrated to give crudeproduct, which was purified by silica gel chromatography (Gradient: 7% to 20% ethyl acetate inpetroleum ether) to give the product as a brown solid. Yield: 5 g, 13 mmol, 68%. LCMS m/z353.0 (M+H). 1H NMR (400 MHz, CD3OD, concentrated HCI), characteristic peaks: oe 8.23-8.26(m, 1H), 8.12 (brd, half of AB quartet, J=8 Hz, 1H), 8.06 (brd, half of AB quartet, J=8 Hz, 1H),7.93 (brd, J=6 Hz, 1H), 7.77-7.81 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 24h; | 6-Bromopyridin-2-amine (274 mg, 1.5 84 mmol) and 2-chloroacetaldehyde (178 mg, 2.268 mmol)were dissolved in EtOH (2 mL). The mixture was heated at 60C for 12 hr. LC-MS showed the formation of the desired product, but there was still starting material remaining. Additional 170 mg of the 2-chloroacetaldehyde was added and the reaction was heated at 60C for 12 hr. LC-MS showed the reaction was completed. After cooling to roomtemperature, the reaction was concentrated. To the resulting residue was added ether, and the solids that precipitated out was collected to give 5-bromoimidazo[1,2-a]pyridine. LC/MS[M+H]: 197.1, 199.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | To a solution of <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> (2.50 g, 12.70 mmol) in THF (40 mL) was added a solution of n-BuLi (1.6 M in hexane, 8.7 mL, 13.90 mmol) dropwise at -78 C. The mixture was stirred at -78 C for 20 minutes, and then Sn(Bu)3Cl (4.13 g, 12.70 mmol) was added. The reaction mixture was stirred at RT for 2 h, diluted with DCM (50 mL), and then filtered through a Celite pad using KF (5: 1). The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (1:2 PE: EA) to afford 5- (tributylstannyl)imidazo[1,2-a]pyridine (1.7 g, 33%) as a colorless oil. LC-MS: m/z, 409.1 [M+H]+;Purity (214 nm): 96%; tR = 1.94 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78℃; | 5-Bromoimidazo[1,2-a]pyridine (500 mg, 2.54 mmol) (commercially available from Fluorochem) and triisopropyl borate (0.589 mL, 2.54 mmol) were dissolved in a mixture of toluene (6 mL) and tetrahydrofuran (1.5 mL). The resulting solution was cooled to -78 C and n-butyl lithium (1.6M in hexanes) (1.586 mL, 2.54 mmol) was added dropwise. The reaction mixture was allowed to slowly warm to 0C and was quenched with isopropanol (1 mL) and left to stir at room temperatureovernight. The reaction mixture was concentrated in vacuo and the residue re-suspended in acetone (20 mL). The resulting cream suspension was filtered and dried in a vacuum oven to give lithium imidazo[1,2-a]pyridin-5-yltriisopropoxyborate (371mg) in approximately 50 % purity and which was used in the subsequent step without further purification. A mixture of tert-butyl 2-(chloromethyl)-6- (methylcarbamoyl)isonicotinate (100 mg, 0.351 mmol), the crude triisopropyl imidazo[1, 2-a] pyrid in15 5-ylborate, lithium salt, prepared as described above (200 mg, approximately 0.320 mmol), Chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1 ?-biphenyl)] pallad ium(II)ligand (41 mg, 0.052 mmol) (commercially available from Aldrich) and tripotassium phosphate (149 mg, 0.702 mmol) in 1,4-dioxane (2 mL) and water (0.500 mL) was heated in a 5 mL microwave vial at 70C in a microwave reactor for 30 mins. The reaction mixture was combined with a previousreaction mixture batch (approximately 50% of the scale of this batch) and was filtered through celite and concentrated to give a crude brown oil. This was purified by chromatography on silica (Biotage SNAP 25g cartridge, eluting with lO-80% of 20% 2M NH3 in MeOH/DCM over 330m1s) to give tertbutyl 2-(imidazo[ 1,2-a] pyridin-5-ylmethyl)-6-(methylcarbamoyl)isonicotinate (141 mg, 0.308 mmol, 88 % yield) as an orange oil and in >80% purity.LCMS (2 mins formic) Peak Rt = 0.61 minutes, m/z= 367 for [MH] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h;Inert atmosphere; | A mixture of <strong>[69214-09-1]5-bromoimidazo[1,2-a]pyridine</strong> (500 mg, 2.54 mmol), Zn(CN)2 (328 mg, 2.79 mmol), and Pd(dppf)Cl2 (186 mg, 0.254 mmol) in NMP (30 mL) was stirred at 140 C. for 2 hour under N2. The mixture was poured into NaHCO3 (aq. 100 mL) extracted with ethyl acetate (30 mL*3). The combined organic phases were washed with brine (50 mL*3), dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1/0 to 1:1) to afford imidazo[1,2-a]pyridine-5-carbonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The mixture of {Pd(cinnamyl)Cl}2 (131 mg, 0.254 mmol) and Mor-DalPhos (235 mg, 0.508 mmol) in dioxane (100 mL) was evacuated with argon (4*). The resulting clear yellow solution was stirred at room temp under argon for 10 min. 5-Bromoimidazo[1,2-a]pyridine (1 g, 5.08 mmol) and t-BuONa (975 mg, 10.2 mmol) were added to the mixture and the mixture was evacuated with argon (4*). The resulting yellow reaction was stirred at room temp for 5 min and was then treated with NH2NH2.H2O (98%, 504 muL, 10.2 mmol) via syringe. The reaction was evacuated with argon (4*). Then the mixture was stirred at 50 C. under argon for 2 h. The mixture was filtered though a pad of diatomaceous earth and washed with ethyl acetate/MeOH (v/v 20/1, 100 mL). The filtrate was collected and concentrated to give crude product as a brown solid (750 mg, crude). It was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With palladium diacetate; ruphos; at 20℃; for 17h;Inert atmosphere; | Intermediate 39 (249.65 mg, 1 mmol) was added to a mixture of 5-bromoimidazo[l,2- a]pyridine (CAS: 69214-09-1; 100 mg, 0.51 mmol), 2-dicyclohexylphosphino-2',6'- diisopropoxy-l,l '-biphenyl (CAS: 787618-22-8; 12 mg, 0.03 mmol) and Pd(OAc)2 (11 mg, 0.05 mmol) under nitrogen atmosphere. The mixture was stirred at rt for 17 h. Then NaHC03 (aq. sat. soltn.) was added and the mixture was extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (silica, EtOAc in heptane from 0/100 to 100/0). The desired fractions were collected and concentrated in vacuo affording intermediate 40 as a yellow oil (24 mg, 16%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.99% | With copper(I) oxide; In N,N-dimethyl acetamide; at 140℃; for 12h; | To a solution of compound 1 (0.5 g, 1.86 mmol, 1 eq) in DMA (5 mL) was added compound 2 (365.83 mg, 1.86 mmol, 1 eq) and Cu2O (132.84 mg, 928.35 umol, 94.88 uL, 0.5 eq). The mixture was stirred at 140C for 12 h. LCMS and showed the reaction was completed. The mixture was filtered to give crude product. The crude product was purified by prep-HPLC (column: Xtimate C18 10m 250 mm *50mm; mobile phase: [water (0.04%NH3H2O)-ACN];B%: 15%-45%,20min) to give compound 3 (50 mg, 129.73 umol, 6.99% yield) as a white solid. LCMS: RT = 0.992 min, MS cal.:385.4, [M+H] + = 386.1 |
Tags: 69214-09-1 synthesis path| 69214-09-1 SDS| 69214-09-1 COA| 69214-09-1 purity| 69214-09-1 application| 69214-09-1 NMR| 69214-09-1 COA| 69214-09-1 structure
[ 1065074-14-7 ]
3,6-Dibromoimidazo[1,2-a]pyridine
Similarity: 0.84
[ 878197-68-3 ]
5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde
Similarity: 0.83
[ 886371-28-4 ]
3-Bromo-6-chloroimidazo[1,2-a]pyridine
Similarity: 0.80
[ 1065074-14-7 ]
3,6-Dibromoimidazo[1,2-a]pyridine
Similarity: 0.84
[ 878197-68-3 ]
5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde
Similarity: 0.83
[ 886371-28-4 ]
3-Bromo-6-chloroimidazo[1,2-a]pyridine
Similarity: 0.80
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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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