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[ CAS No. 1186663-31-9 ] {[proInfo.proName]}

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Chemical Structure| 1186663-31-9
Chemical Structure| 1186663-31-9
Structure of 1186663-31-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1186663-31-9 ]

CAS No. :1186663-31-9 MDL No. :MFCD12198864
Formula : C6H8Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :YFYBPPVXPGYHTE-UHFFFAOYSA-N
M.W : 179.05 Pubchem ID :53429573
Synonyms :

Calculated chemistry of [ 1186663-31-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.37
TPSA : 38.91 Ų

Pharmacokinetics

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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.23
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 1.26

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.12 mg/ml ; 0.00625 mol/l
Class : Soluble
Log S (Ali) : -1.81
Solubility : 2.77 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.391 mg/ml ; 0.00218 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 1186663-31-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 UN#:3261
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1186663-31-9 ]

* 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.

  • Downstream synthetic route of [ 1186663-31-9 ]

[ 1186663-31-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 105250-17-7 ]
  • [ 1186663-31-9 ]
YieldReaction ConditionsOperation in experiment
76% With pyridine; thionyl chloride; at 75℃; for 8h; 4ml of pyridine as a catalyst was added to 110ml of thionyl chloride solution of <strong>[105250-17-7](2-aminopyridine-4-yl)methanol</strong> (31g, 0.25mol). The solution was kept at 75°C and refluxed for 8 hours. Then, excessive thionyl chloride was removed under reduced pressure, and the residue was refined by chromatography (dichloromethane/methanol, 50/1) to obtain 4-(chloromethyl)pyridine-2-amine hydrochloride (33.8g, 76percent) (Compound 4). M.W. : 179(hydrochloride); EI-MS:142(M+)
With thionyl chloride; at 0 - 50℃; for 2h; Intermediate I: Preparation of 2-[4-(chloromethyl)pyridin-2-yl]amino}-2-oxoethyl acetate; Step 1: Preparation of 4-(chloromethyl)pyridin-2-amine; (2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 inmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 °C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SC>4) and evaporated in vacuo to yield 10.71 g (83percent) of pure title compound.'H NMR (300 MHz, DMSO-J6) 6 7.87 (d, 1H), 6.48 (d, 1H), 6.45 (s, 1H), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.
With thionyl chloride; at 0 - 50℃; for 2h; (2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 mmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 °C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SO4) and evaporated in vacuo to yield 10.71 g (83percent) of pure title compound. 1H NMR (300 MHz, DMSO-J6) delta 7.87 (d, IH), 6.48 (d, IH), 6.45 (s, IH), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.
With thionyl chloride; at 20℃; for 2h; Preparation of 4-(chloromethyl')pyridin-2~amine(2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 mmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SO4) and evaporated in vacuo to yield 10.71 g (83percent) of pure title compound.1H NMR (300 MHz, DMSO-J6) 67.87 (d, IH), 6.48 (d, IH), 6.45 (s, IH), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.

  • 2
  • [ 1186663-31-9 ]
  • [ 872706-97-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydrogencarbonate In dichloromethane for 1.5h; E.1 Preparation of 4-(chloromethyl')pyridin-2~amine(2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 mmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SO4) and evaporated in vacuo to yield 10.71 g (83%) of pure title compound.1H NMR (300 MHz, DMSO-J6) 67.87 (d, IH), 6.48 (d, IH), 6.45 (s, IH), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.
With sodium hydrogencarbonate In dichloromethane; water for 1.5h; I.1 Intermediate I: Preparation of 2-[4-(chloromethyl)pyridin-2-yl]amino}-2-oxoethyl acetate; Step 1: Preparation of 4-(chloromethyl)pyridin-2-amine; (2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 inmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 °C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SC>4) and evaporated in vacuo to yield 10.71 g (83%) of pure title compound.'H NMR (300 MHz, DMSO-J6) 6 7.87 (d, 1H), 6.48 (d, 1H), 6.45 (s, 1H), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.
With sodium hydrogencarbonate In dichloromethane; water for 1.5h; J.1 (2-Aminopyridin-4-yl)methanol (11.2 g, 90 mmol) was stirred in a flask with ice bath cooling as thionyl chloride (65.8 mL, 902 mmol) was slowly added. After about 10 mL was added, the temperature increased suddenly to about 50 °C and addition was halted as the mixture was broken up so that stirring could continue as the rest of the thionyl chloride was added. The cooling bath was then removed and the reaction was stirred for 2 h at ambient temperature before it was evaporated in vacuo and then toluene was added twice and evaporated each time in vacuo to yield the hydrochloride salt of the title compound. A suspension of this material in dichloromethane (150 mL) was stirred with saturated aqueous sodium bicarbonate (150 mL) for 1.5 h. The phases were separated and the organic extract was washed twice with water, once with brine and then dried (Na2SO4) and evaporated in vacuo to yield 10.71 g (83%) of pure title compound. 1H NMR (300 MHz, DMSO-J6) δ 7.87 (d, IH), 6.48 (d, IH), 6.45 (s, IH), 6.04 (s, 2H) and 4.60 ppm (s, 2H); ES-MS m/z 143.2 [M+H]+, HPLC RT (min) 1.34.
  • 3
  • [ 1186663-31-9 ]
  • [ 17356-08-0 ]
  • (2-aminopyridine-4-yl)methyl carbamimidothioate dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol; water at 80℃; for 3h; Inert atmosphere; 6.9d Synthesis of (2-aminopyridine-4-yl)methylcarbamimidethioacid hydrochloride (Compound 5) [3] Compound 4 (26.7g, 0.15mol) and 150ml of ethanol aqueous solution of thiourea (15.2g, 0.2ml) were stirred for 3 hours at 80°C under a nitrogen atmosphere. After cooling at room temperature, the solution was filtered and the residue was washed by ethanol. Compound 7 (28.9g, 76%) was obtained by crystallization using 95% ethanol. (0523) 1H-NMR (d6-DMSO, 300MHz) : δ3.69 (br, 5H, NH) ; 4.67(S, 2H); 6.88(d, 1H); 7.10(S, 1H); 7.98(d, 1H); 8.09 (br, 2H, NH).
  • 4
  • [ 1186663-31-9 ]
  • [ 64-19-7 ]
  • N-(4-(chloromethyl)pyridin-2-yl)acetamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.6 g Stage #1: acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Stage #2: 4-(chloromethyl)pyridine-2-amine hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; 7 Example 7: N-(4-(chloromethyl)pyridin-2-yl)acetamide hydrochloride (Compound 26) The reaction flask was charged with acetic acid (27 mmol), DCM (100 mL) and 10 drops of DMF, and oxalyl chloride (81 mmol) was added dropwise with stirring at 0 ° C. After the dropwise addition, the mixture was stirred at room temperature for 2 hours, the solvent and excess oxalyl chloride were evaporated to dryness under reduced pressure. Subsequently, DCM (100 mL), TEA (40.5 mmol) and 2-amino-4-chloromethylpyridine hydrochloride (27 mmol) were added and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, dissolved in acetone (8 mL) EA was added dropwise with stirring to give a solid precipitate to give a total of 4.6 g of a white solid (Compound 26).
  • 5
  • [ 1186663-31-9 ]
  • [ 98-57-7 ]
  • 4-chloromethyl-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 40℃; for 20h; 10 Example 10: 4-chloromethyl-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine (Compound 29) The reaction flask was charged with 2-amino-4-chloromethylpyridine hydrochloride (53.3 mmol), 4-chlorophenylmethylsulfone (79.9 mmol), K2CO3 (239.8 mmol), NaI (7.99 mmol) and DMF (250mL). The system was stirred at 40 ° C for 20 hours, diluted with water (250 mL), extracted with EA (3 * 250 mL), washed with saturated NaCl (250 mL), dried over anhydrous Na2SO4, Filtered and evaporated to dryness under reduced pressure. Column chromatography gave 7.9 g of crude product (Compound 29).
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