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Chemical Structure| 211308-81-5
Chemical Structure| 211308-81-5
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Product Details of [ 211308-81-5 ]

CAS No. :211308-81-5 MDL No. :MFCD07644578
Formula : C5H4ClIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :DIONPYCYVWCDIG-UHFFFAOYSA-N
M.W : 254.46 Pubchem ID :11076010
Synonyms :

Calculated chemistry of [ 211308-81-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.37
TPSA : 38.91 Ų

Pharmacokinetics

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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.236 mg/ml ; 0.000928 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.55 mg/ml ; 0.00609 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.148 mg/ml ; 0.000581 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.05

Safety of [ 211308-81-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 211308-81-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 211308-81-5 ]
  • Downstream synthetic route of [ 211308-81-5 ]

[ 211308-81-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1072-98-6 ]
  • [ 211308-81-5 ]
YieldReaction ConditionsOperation in experiment
90.1% With N-Bromosuccinimide In tetrahydrofuran; 1,2-dichloro-ethane at 53℃; for 7 h; A mixed solvent of tetrahydrofuran and dichloroethane 24150 ml of tetrahydrofuran was added to a 50 L reactor.8000ml, insert thermometer to start mechanical stirrer and add 6037.5g2-amino-5-chloropyridine, 18528 g of N-iodosuccinimide was added, and the reaction was continued for 7 hours while stirring at a reaction temperature of 53C.TLC and GC confirmed that the reaction 2-amino-5-chloropyridine was complete. The solvent is removed by rotary evaporation to give a crude product.Recrystallization from a mixed solvent of ethyl acetate and ethanol gives a pure product2-Amino-3-iodo-5-chloropyridine, after drying, the calculated yield was 90.10percent, and the GC detection purity was 98.2percent
85% With sulfuric acid; iodine; periodic acid In water; acetic acid at 80℃; for 6 h; Cooling with ice First Step
To a mixed solution of 2-amino-5-chloropyridine (2.6 g, 0.020 mol) in acetic acid/water (7.8 mL/1.8 mL) that cooled with ice bath, conc. sulfuric acid (0.26 mL, 4.9 mmol) was added dropwise, and then periodic acid (0.95 g, 4.2 mmol) and iodine (2.0 g, 8.0 mmol) were added.
The reaction mixture was stirred at 80° C. for 6 h.
Cooled to ambient temperature, the reaction mixture was poured into ice water, and neutralized by aqueous 5M sodium hydroxide solution.
After removal of the precipitate by filtration, the filtrate was extracted with ethyl acetate.
The organic layer was washed with saturated sodium thiosulfate solution, aqueous 1M sodium hydroxide solution and brine then dried over sodium sulfate and concentrated to afford 2-amino-5-chloro-3-iodopyridine as solid (4.4 g, y. 85percent).
1H NMR (CDCl3) δ (ppm) 7.96 (s, 1H), 7.82 (s, 1H), 4.93 (s, 2H); LCMS (m/z) 255.2 [M+H]+.
84%
Stage #1: at 100℃;
Stage #2: With potassium iodide In water for 1.5 h;
Step 1 : 5-Chloro-3-iodo-pyridin-2-ylamineA stirred solution of 5-chloro-pyridin-2-ylamine (51.4 g, 0.40 mol) in 2M sulfuric acid (700 mL) was treated portionwise with potassium iodate (43.7 g, 0.2 mol) and the mixture heated to 100 °C. A solution of potassium iodide (36.5 g, 0.55 mol) in water (100 mL) was added dropwise over ca. 1 hour. The mixture was allowed to stir for a further 30 minutes then cooled to ambient temperature. The pH of the aqueous phase was adjusted to 8-9 and the mixture extracted with ethyl acetate (x 3). The combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine, dried (Na2S04), filtered and evaporated to afford the title compound as a tan solid (86.3 g, 84percent). LCMS (Method B): RT = 3.76 min, M+H+ = 255/257. NMR (400 MHz, CDC13): 7.98 (d, J = 2.3 Hz, 1H), 7.84 (d, J = 2.3 Hz, 1H), 5.03 (s, 2H).
80% With sulfuric acid; iodine; acetic acid; periodic acid In water at 80℃; for 6 h; A round bottom flask equipped with an air condenser was charged with 5-chloropyridin-2-ylamine (26g, 0.2mol), acetic acid (78ml) and water (18ml). This was followed by dropwise addition of concentrated sulphuric acid (2.6ml), portionwise addition of periodic acid (9.5g, 0.04mol), and iodine (20g, 0.08mol). The reaction mixture was vigorously stirred at 80°C for 6h and then allowed to cool the room temperature. The reaction mixture was poured onto ice (~700g). The pH of the suspension was adjusted to 8-9 with a 5M aqueous NaOH solution. A brown solid was filtered off and solubilised in EtOAc (1.21). The organic was washed with a saturated aqueous solution of Na2S2O3, 1M NaOH solution and brine. The organic was dried over MgS04 and concentrated. The residue was recristallised from cyclohexane to afford an orange solid (42g, 80percent). 1H NMR (CDCl3) : 4.8-5.1 (2H, brs), 7.9 (1H, s), 8.0 (1H, s)
68% at 20℃; Step 15-Chloro-3-iodopyridin-2-amine Procedure:To a solution of 5-chloropyridin-2-amine (10.0 g, 78.1 mmol) and iodine (39.7 g, 156.2 mmol) in EtOH (500 mL), Ag2SO4 (48.7 g, 156.2 mmol) was added portion-wise at ambient temperature. The final mixture was then stirred overnight at ambient temperature. The formed solid (AgI) was removed by filtration; the filtrate was evaporated to dryness. The residue was dissolved in DCM (1 L), washed by saturated Na2S2O3 (aq., 2.x.50 ml), brine (2.x.50 mL), dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (silica gel, 200-300 mesh, dichloromethane as eluent) to give 5-chloro-3-iodopyridin-2-amine (13.5 g, 68percent) as yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.99 (brs, 1H), 7.83 (s, 1H), 5.00-4.94 (m, 2H). LC/MS: 254.9 [M+H]+.
68% With iodine; silver sulfate In ethanol at 20℃; To a solution of 5-chloropyridin-2-amine (10.0 g, 78.1 mmol) and iodine (39.7 g, 156.2 mmol) in EtOH (500 mL), Ag2S04 (48.7 g, 156.2 mmol) was added portion-wise at ambient temperature. The final mixture was then stirred overnight at ambient temperature. The formed solid (Agl) was removed by filtration; the filtrate was evaporated to dryness. The residue was dissolved in DCM (1 L), washed by saturated Na2S203 (aq., 2 50 ml), brine (2 50 mL), dried over Na2S04 and concentrated. The crude product was purified by column chromatography (silica gel, 200 - 300 mesh, dichloromethane as eluent) to give 5- chloro-3-iodopyridin-2-amine (13.5g, 68 percent) as yellow solid. 1H NMR (300 MHz, CDC13): δ 7.99 {brs, 1H), 7.83 (s, 1H), 5.00 - 4.94 (m, 2H). LC/MS: 254.9 [M + H]+.
64% With iodine; silver sulfate In ethanol at 20℃; INTERMEDIATE 81 - PREPARATION of 5-chloro-3-iodopyridin-2-amine. Iodine (7.55 g; 29.73 mmol) was added to a mixture of 5-chloropyridin-2-amine (3.00 g; 22.87 mmol) and silver sulfate (9.36 g; 29.73 mmol) in ethanol (150 ml_) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite, washed with ethanol, and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with a saturated aqueous solution of sodium thiosulfate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue purified by flash chromatography on silica gel (eluent 0 to 30percent ethyl acetate in heptane) to give 3.71 g (64percent) of 5-chloro-3-iodopyridin-2-amine as a beige solid. ESI/APCI(+) : 255 (M+Na); 1 H NMR (CDCI3) d 7.99 (d, 1 H); 7.84 (d, 1 H), 4.96 (s, 2H).
64% With iodine; silver sulfate In ethanol at 20℃; Iodine (7.55 g; 29.73 mmol) was added to a mixture of 5-chloropyridin-2-amine (3.00 g; 22.87 mmol) and silver sulfate (9.36 g; 29.73 mmol) in ethanol (150 mL) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite, washed with ethanol, and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with a saturated aqueous solution of sodium thiosulfate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue purified by flash chromatography on silica gel (eluent 0 to 30percent ethyl acetate in heptane) to give 3.71 g (64percent) of 5-chloro-3-iodopyridin-2-amine as a beige solid. [0701] ESI/APCI(+): 255 (M+Na); 1H NMR (CDCl3) d 7.99 (d, 1H); 7.84 (d, 1H), 4.96 (s, 2H).
64.5% With iodine; silver sulfate In ethanol at 20℃; for 22 h; Inert atmosphere; Schlenk technique To a solution of 2-amino-5-chloropyridine (3.00 g, 23.3 mmol) in ethanol (30.0 mL) was added Ag2SO4 (8.73 g, 28.0 mmol) followed by adding a solution of I2 (5.92 g, 23.3 mmol) in ethanol (125 mL). After the mixture was stirred for 22 h at room temperature, the insoluble was filtered off, and volatiles were removed under reduced pressure. The residue was re-dissolved in dichloromethane (DCM) and washed with a saturated solution of aqueous sodium thiosulfate. The organic layer was collected and dried over anhydrous MgSO4, and the volatile was removed under reduced pressure. The resulting residue was purified by silica-gel column chromatography (THF/hexane, 1:8 v/v) to afford pure L1 as an orange solid (3.80 g, 64.5 percent yield).
64% With iodine; silver sulfate In ethanol at 20℃; INTERMEDIATE 159 - PREPARATION of 5-chloro-3-iodopyridin-2-amine; Iodine (7.55 g; 29.73 mmol) was added to a mixture of 5-chloropyridin-2-amine (3.00 g; 22.87 mmol) and silver sulphate (9.36 g; 29.73 mmol) in ethanol (150 ml.) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite, washed with ethanol, and the filtrate concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the solution was washed with a saturated aqueous solution of sodium thiosulphate. The organic layer was dried over magnesium sulphate, concentrated under reduced pressure and the crude material purified by flash chromatography on silica gel (eluent : 0 to 30percent of ethyl acetate in heptane) to give 3.71 g (64percent) of 5-chloro-3-iodopyridin-2-amine as a beige solid. ESI/APCI(+) : 255 (M+Na). 1 H NMR (CDCI3) δ 7.99 (d, 1 H); 7.84 (d, 1 H), 4.96 (s, 2H).
60% With iodine; silver sulfate In ethanol at 20℃; for 2 h; Iodine (16.28 g, 64 mmol) was added to a mixture of 1-amino-5-chloropyridine (8.25 g, 64 mmol) and silver sulfate (20 g, 64 mmol) in 400 mL of ethanol and the mixture was stirred at rt for 20 h. The mixture was filtered over celite and the solvent removed in vacuo. The residue was dissolved in DCM (600 mL) and washed with 5percent aqueous NaOH (500 mL), water and brine. The organic layer was dried and concentrated in vacuo to solid residue that was subjected to flash chromatography (20percent EtOAc-80percent hexanes) to give 9.8 g (60percent) of 40. 1H NMR (500 MHz, CDCl3) 7.9 (s, 1H), 7.7 (s, 1H), 5.0 (bs, 2H).
60%
Stage #1: at 85℃;
Example 5; Synthesis of Compound 21 Step 1. The solution of 2-amino-5-chloropyridine (10.0 g, 77.8 mmol) potassium acetate (7.63 g, 77.8 mmol) in 100 mL of acetic acid was heated to 85° C. and ClI (12.6 g, 77.8 mmol) in 50 mL of acetic acid was added dropwise. Reaction mixture was kept 2 h at this temperature, diluted with 1 L of water, neutralized with NaOH 1N solution to pH 7 and extracted with ethyl acetate (4.x.75 mL). Organic fraction were combined, washed with NaHCO3, filtered through celite and evaporated. The residue was subjected to column chromatography on silica (eluent-hexane/ethyl acetate 1/1) providing 5-chloro-3-iodopyridin-2-amine as yellow solid (11.9 g, 60percent).
56%
Stage #1: With sulfuric acid; iodine; periodic acid In ethanol; water at 80℃; for 15 h;
Stage #2: With sodium hydroxide In ethanol; water
Into a 5000-mL 4-necked round-bottom flask was placed a solution of 5-chloro- pyridin-2-amine (520 g, 4.03 mol, 1.00 equiv) in ethanol (1560 mL) and water (360 mL). To this was added sulfuric acid (52 mL) dropwise with stirring. This was followed by addition of H5I06 (190 g, 833.33 mmol, 0.20 equiv) in several batches at 30°C. To the mixture was added 12 (400 g, 1.57 mol, 0.40 equiv) in several batches. The resulting solution was stirred for 15 h at 80°C in an oil bath. The resulting solution was diluted with 14000 mL of ice water. The pH value of the solution was adjusted to 9 with sodium hydroxide solution (5M). The solid was collected by filtration. Then it was dissolved in 20000 mL of EtOAc and washed with 1x1000 mL of Na2S204 solution. The EtOAc solution was treated with sodium hydroxide solution (1 M) till pH 9 was reached. The separated organic layer was washed with 2x1000 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with, ethyl acetate/petroleum ether (0-0.03). This resulted in 580 g (56percent) of 5-cMoro-3 odopyridin-2-amine as a brown solid.
54% With iodine; silver sulfate In ethanol; dichloromethane 5-Chloro-3-iodo-2-pyridinamine
Iodine (13.2 g, 52 mmol) was added to a mixture of 5-chloro-2-pyridinamine (6.68 g, 52 mmol) and silver sulfate (16.2 g, 52 mmol) in ethanol (350 mL) and the mixture was stirred at room temperature for 20 h.
The mixture was filtered through a glass fibre pad and the solvent was evaporated under reduced pressure.
The residue was dissolved in dichloromethane (600 mL), washed with aqueous sodium hydroxide (5percent, 500 mL), water (500 mL) and brine (500 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure.
The residue was purified by flash column chromatography on silica gel, eluding with isohexane/EtOAc (80:20), to give the title compound as a pale orange solid (7.1 g, 54percent).
1H NMR (360 MHz, CDCl3) δ 7.99 (1H, d, J 2.2 Hz), 7.84 (1H, d, J 2.2 Hz), and 4.94 (2H, br s).
m/z (ES+) 255, 257 (M+1).
17.3% With N-chloro-succinimide; acetic acid In benzene at 100℃; [00395] To a solution of 2-amino-5-chloropyridine (5.11 g, 39.7 mmol) in benzene (110 niL) and AcOH (2.3 mL) was added N-iodosuccinimide (8.94 g, 39.7 mmol). The reaction mixture was allowed to stir at 100 °C overnight. The mixture was diluted with EtOAc and washed with saturated NaHCO3 and brine. The organic solution was dried over sodium sulfate, filtered and evaporated to afford crude product as dark red solid. The crude product was redissolved in EtOAc and washed with sodium bisulfite solution twice followed by brine.. The solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography to afford 5-chloro-3- iodopyridin-2-amine as a yellow powder (1.75 g, 17.3percent). LCMS (FA): m/z 254.0 (M+H).
17.3% With N-iodo-succinimide; acetic acid In benzene at 100℃; Step 1:
5-chloro-3-iodopyridin-2-amine
To a solution of 2-amino-5-chloropyridine (5.11 g, 39.7 mmol) in benzene (110 mL) and AcOH (2.3 mL) was added N-iodosuccinimide (8.94 g, 39.7 mmol).
The reaction mixture was allowed to stir at 100° C. overnight.
The mixture was diluted with EtOAc and washed with saturated NaHCO3 and brine.
The organic solution was dried over sodium sulfate, filtered and evaporated to afford crude product as dark red solid.
The crude product was redissolved in EtOAc and washed with sodium bisulfite solution twice followed by brine.
The solution was dried over Na2SO4, filtered and concentrated.
The crude product was purified by column chromatography to afford 5-chloro-3-iodopyridin-2-amine as a yellow powder (1.75 g, 17.3percent). LCMS (FA): m/z=254.0 (M+H).

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[3] Patent: US2014/18533, 2014, A1, . Location in patent: Paragraph 0074; 0075
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[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 307 - 315
[3] Patent: US2014/18533, 2014, A1,
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  • [ 211308-81-5 ]
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  • [ 1001014-88-5 ]
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  • [ 211308-81-5 ]
  • [ 800401-84-7 ]
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[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 51
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  • [ 866546-09-0 ]
Reference: [1] Patent: WO2011/137022, 2011, A1,
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