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[ CAS No. 1394838-36-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1394838-36-8
Chemical Structure| 1394838-36-8
Chemical Structure| 1394838-36-8
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Product Details of [ 1394838-36-8 ]

CAS No. :1394838-36-8 MDL No. :MFCD22495122
Formula : C6H4Cl2FN Boiling Point : -
Linear Structure Formula :- InChI Key :PRHYENAVAPCCBW-UHFFFAOYSA-N
M.W :180.01 Pubchem ID :60150235
Synonyms :

Calculated chemistry of [ 1394838-36-8 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 40.82
TPSA : 26.02 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) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 3.14
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.165 mg/ml ; 0.000916 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.288 mg/ml ; 0.0016 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.051 mg/ml ; 0.000283 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 1394838-36-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1394838-36-8 ]

* 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 [ 1394838-36-8 ]

[ 1394838-36-8 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic acid / methanol / 3 h / 20 °C 1.2: 16 h / 60 °C 2.1: thionyl chloride / 2 h / 20 °C 2.2: 16 h / 20 °C 3.1: aniline; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 2 h / 20 °C
  • 2
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / methanol / 3 h / 20 °C 1.2: 16 h / 60 °C 2.1: thionyl chloride / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 3
  • [ 50-00-0 ]
  • [ 1394838-36-8 ]
  • [ 2464742-32-1 ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: formaldehyd; C6H4Cl2FN With acetic acid In methanol at 20℃; for 3h; Stage #2: With sodium cyanoborohydride In methanol at 60℃; for 16h; 265 Synthesis of 265.2: To a stirred solution of 265.1 (500 mg, 2.77 mmol) in MeOH (10 mL) were added paraformaldehyde (0.083 g, 2.77 mmol) and AcOH (0.1 mL, cat.) at RT. After stirring for 3 h at RT, NaCNBTb (523 mg, 8.33 mmol) was added. After stirring for 16 h at 60 °C, the reaction mixture was evaporated under reduced pressure, diluted with H2O (25 mL) and extracted with EtOAc (2 x 15 mL). The combined organic layer was dried over anhydrous Na2SC>4, filtered and concentrated under reduced pressure. The residue was purified by (Silica gel 100-200 mesh, 2% EtO Ac/hexane) to afford 265.2 (200 mg, 37%) as a yellow liquid. (0810) 1HNMR (400 MHz, CDCb): 6.69-6.63 (m, 1H), 6.55-6.49 (m, 1H), 4.12 (br s, 1H), 2.87 (d, J= 5.2 Hz, 3H); LCMS: 94.7%, m/z [M+H]+= 194.0.
  • 4
  • [ 1394838-36-8 ]
  • [ 2228210-11-3 ]
  • [ 2853484-00-9 ]
YieldReaction ConditionsOperation in experiment
42% With lithium perchlorate In diethyl ether at 40℃; for 20h; Inert atmosphere;
42% With lithium perchlorate In diethyl ether at 40 - 60℃; Inert atmosphere;
  • 5
  • [ 1002-18-2 ]
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
41% With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice; Synthesis of 2-(3,5-dichloro-2-fluorophenyl)isothiazol-3(2H)-one (ISFP5) 3,3'-Dithiodipropionic acid (1 g, 4.76 mmol) was placedunder an argon atmosphere in a dry round bottom ask(sealed with a turnover septum) and was dissolved in anhy-drous tetrahydrofuran (20 ml). The ask was then cooled on-ice followed by the dropwise addition of thionyl chloride(2.07 ml, 28.53 mmol) with stirring. N,N-dimethylformamide(74 μ l, 0.95 mmol) was then added to the stirring solution, andthe reaction was left to stir on ice for 20 min, at which pointthe ice was removed and the reaction was allowed to warm toroom temperature. The reaction was stirred at room temper-ature for a further 3 h at which point the ask was purged withargon and the solvent was carefully removed in vacuo using arotary evaporator (no heating). The resulting crude materialwas triturated twice using toluene followed by solvent removalin vacuo (no heating). The crude material was again dissolvedin tetrahydrofuran ( < 10 ml) and was evaporated to dryness invacuo (no heating). The crude material was subsequently usedwithout further puri cation.3,5-dichloro-2- uoroaniline (1 g, 5.5 mmol) was dissolved inanhydrous dichloromethane (5 ml) under an argon atmo-sphere. Triethylamine (6.95 mmol, 969 μ l) was then added tothe stirring solution and cooled on-ice. Separately, 3,30-disul-fanediyldipropionyl chloride from the rst reaction (344 mg,1.39 mmol) was suspended in anhydrous dichloromethane(5 ml) and was then added slowly to the stirring 3,5-dichloro-2- uoroaniline solution. The reaction was allowed to stir on-ice for 30 min, then warmed to room temperature, andallowed to stir overnight. The next day, a saturated aqueoussolution of sodium hydrogen carbonate (approx. 40 ml) wasadded slowly to the crude reaction mixture and the resultingsolution was extracted using dichloromethane (3 × 20 mlminimum). The organic phase was dried over sodium sulfate, ltered, and the solvent removed in vacuo (water bath at 35C). The crude material was dry loaded on silica and waspuri ed by ash chromatography (Heptane/Ethyl acetate (2:1)→ Ethyl acetate) (305 mg, 41% yield).The product, 3,30-disulfanediylbis(N-(3,5-dichloro-2- uorophenyl)propanamide) (210 mg, 0.39 mmol) was sus-pended (not dissolved) in anhydrous dichloromethane underan argon atmosphere and was cooled on-ice. A solution of1M sulfuryl chloride in dichloromethane ( 1 eq., 393 μ l) wasthen added to the stirring ask and was stirred for 15 min.Over the course of the following 1 to 2 h, an additional 4 to 5equivalents of sulfuryl chloride solution was added to thestirring solution until the solubility of the material in the ask improved. At this point, the reaction mixture wasallowed to warm to room temperature and stirred overnight.The next day, saturated brine solution (approx. 20 ml) was added to the off-white suspension followed by extractionwith ethyl acetate (3 × 20 ml minimum). The organic phasewas dried over sodium sulfate, ltered, and the solventremoved in vacuo (water bath at 30C) to the point wherethe solid crude product became visible in the ask. At thispoint, the reaction mixture was resolubilized with the mini-mum amount of solvent and was dry loaded onto silica for ash puri cation (Heptane/ethyl acetate (1:1) → ethyl ace-tate). The ash puri ed material then underwent a furtherpuri cation by reverse phase C18 HPLC (see supplementaryinformation for methods) (R f : 0.65; heptane/ethyl acetate,1:1) (19 mg, postlyophilisation, 18% yield).
41% With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice; Synthesis of 2-(3,5-dichloro-2-fluorophenyl)isothiazol-3(2H)-one (ISFP5) 3,3'-Dithiodipropionic acid (1 g, 4.76 mmol) was placedunder an argon atmosphere in a dry round bottom ask(sealed with a turnover septum) and was dissolved in anhy-drous tetrahydrofuran (20 ml). The ask was then cooled on-ice followed by the dropwise addition of thionyl chloride(2.07 ml, 28.53 mmol) with stirring. N,N-dimethylformamide(74 μ l, 0.95 mmol) was then added to the stirring solution, andthe reaction was left to stir on ice for 20 min, at which pointthe ice was removed and the reaction was allowed to warm toroom temperature. The reaction was stirred at room temper-ature for a further 3 h at which point the ask was purged withargon and the solvent was carefully removed in vacuo using arotary evaporator (no heating). The resulting crude materialwas triturated twice using toluene followed by solvent removalin vacuo (no heating). The crude material was again dissolvedin tetrahydrofuran ( < 10 ml) and was evaporated to dryness invacuo (no heating). The crude material was subsequently usedwithout further puri cation.3,5-dichloro-2- uoroaniline (1 g, 5.5 mmol) was dissolved inanhydrous dichloromethane (5 ml) under an argon atmo-sphere. Triethylamine (6.95 mmol, 969 μ l) was then added tothe stirring solution and cooled on-ice. Separately, 3,30-disul-fanediyldipropionyl chloride from the rst reaction (344 mg,1.39 mmol) was suspended in anhydrous dichloromethane(5 ml) and was then added slowly to the stirring 3,5-dichloro-2- uoroaniline solution. The reaction was allowed to stir on-ice for 30 min, then warmed to room temperature, andallowed to stir overnight. The next day, a saturated aqueoussolution of sodium hydrogen carbonate (approx. 40 ml) wasadded slowly to the crude reaction mixture and the resultingsolution was extracted using dichloromethane (3 × 20 mlminimum). The organic phase was dried over sodium sulfate, ltered, and the solvent removed in vacuo (water bath at 35C). The crude material was dry loaded on silica and waspuri ed by ash chromatography (Heptane/Ethyl acetate (2:1)→ Ethyl acetate) (305 mg, 41% yield).The product, 3,30-disulfanediylbis(N-(3,5-dichloro-2- uorophenyl)propanamide) (210 mg, 0.39 mmol) was sus-pended (not dissolved) in anhydrous dichloromethane underan argon atmosphere and was cooled on-ice. A solution of1M sulfuryl chloride in dichloromethane ( 1 eq., 393 μ l) wasthen added to the stirring ask and was stirred for 15 min.Over the course of the following 1 to 2 h, an additional 4 to 5equivalents of sulfuryl chloride solution was added to thestirring solution until the solubility of the material in the ask improved. At this point, the reaction mixture wasallowed to warm to room temperature and stirred overnight.The next day, saturated brine solution (approx. 20 ml) was added to the off-white suspension followed by extractionwith ethyl acetate (3 × 20 ml minimum). The organic phasewas dried over sodium sulfate, ltered, and the solventremoved in vacuo (water bath at 30C) to the point wherethe solid crude product became visible in the ask. At thispoint, the reaction mixture was resolubilized with the mini-mum amount of solvent and was dry loaded onto silica for ash puri cation (Heptane/ethyl acetate (1:1) → ethyl ace-tate). The ash puri ed material then underwent a furtherpuri cation by reverse phase C18 HPLC (see supplementaryinformation for methods) (R f : 0.65; heptane/ethyl acetate,1:1) (19 mg, postlyophilisation, 18% yield).
  • 6
  • [ 49574-55-2 ]
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
48% With lithium perchlorate In diethyl ether at 40℃; for 20h; Inert atmosphere;
  • 7
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 2: sulfuric acid; HNO3 / 1 h / -10 - 20 °C / Inert atmosphere
  • 8
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 2.1: sulfuric acid; HNO3 / 1 h / -10 - 20 °C / Inert atmosphere 2.2: 6 h / 60 °C / Inert atmosphere
  • 9
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 2.1: sulfuric acid; HNO3 / 1 h / -10 - 20 °C / Inert atmosphere 2.2: 6 h / 60 °C / Inert atmosphere 3.1: lithium perchlorate / diethyl ether / 72 h / 60 °C / Inert atmosphere
  • 10
  • [ 1394838-36-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 2.1: sulfuric acid; HNO3 / 1 h / -10 - 20 °C / Inert atmosphere 2.2: 6 h / 60 °C / Inert atmosphere 3.1: lithium perchlorate / diethyl ether / 20 h / 40 °C / Inert atmosphere
  • 11
  • [ 1394838-36-8 ]
  • [ 75-36-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
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