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[ CAS No. 1186663-18-2 ] {[proInfo.proName]}

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Chemical Structure| 1186663-18-2
Chemical Structure| 1186663-18-2
Structure of 1186663-18-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1186663-18-2 ]

CAS No. :1186663-18-2 MDL No. :MFCD11052339
Formula : C9H10ClF2N Boiling Point : -
Linear Structure Formula :- InChI Key :TYWIBZMFYNGWIX-UHFFFAOYSA-N
M.W : 205.63 Pubchem ID :53429563
Synonyms :

Calculated chemistry of [ 1186663-18-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.38
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 3.38
Log Po/w (MLOGP) : 2.93
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.381 mg/ml ; 0.00185 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 1.01 mg/ml ; 0.00492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.0802 mg/ml ; 0.00039 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 1186663-18-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1186663-18-2 ]

* 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 [ 1186663-18-2 ]

[ 1186663-18-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1335210-34-8 ]
  • [ 1186663-18-2 ]
  • [ 1656286-80-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 0.5h; 5.1 Example 5 Preparation of Compound 5 (4R., 12aS)-N-(l-(2,4-difluoropheny].)cyclopropyl)-7-hydroxy-4-methyi-6,8-dioxo- 3,4,6,8, 12, i2a-hexahydro-2H-[l ,3]oxazino[3,2-d]pyrido[l ,2-a]pyrazine-9-carboxamide Step 1 Example 5 Preparation of Compound 5 (4R., 12aS)-N-(l-(2,4-difluoropheny].)cyclopropyl)-7-hydroxy-4-methyi-6,8-dioxo- 3,4,6,8, 12, i2a-hexahydro-2H-[l ,3]oxazino[3,2-d]pyrido[l ,2-a]pyrazine-9-carboxamide Step 1 (4R,12aS)-7-methoxy-4-methyl-6,8-dioxo-3 ,4,6,8, 12, 12a-hexahydro- 2H-[l ,3]oxazino[3,2-d]pyrido[ l ,2-a]pyrazine-9-carboxylic acid (Intermediate 5- A) was prepared in an analogous manner to (3S,l laR)-6-methoxy-3-methyl-5,7-dioxo- 2,3,5,7, 1 1 ,1 la-hexahydrooxazolo[3,2-d]pyrido[l ,2-a]pyrazine-8-carboxylic acid as described in WO201 1/1 19566, substituting (R)-3-aminobutan~l~ol for (S)-2~ aminopropan-l-ol . WO20.i l 1 19566 is incorporated herein by reference in its entirety. A suspension of Intermediate 5-A (24.8 mg, 0.080 mmol ), l-(2,4- difluoropheny].)cyclopropanamine HC1 salt (5-15, 21.9 mg, 0.107 mmol), and HATU (48 mg, 0.126 mmol) in CH2C12 (2 mL) was stirred at ambient temperature as N,N- diisopropylethyl amine (DIPEA) (0.1 mL, 0.574 mmol) was added. After 30 minutes, the reaction mixture was diluted with ethyl acetate before washing with 10% aqueous citric acid solution (xl) and saturated aqueous NaHC03 solution (xl). After the aqueous fractions were extracted with ethyl acetate (x l), the organic fractions were combined, dried (MgS04), and concentrated. The residue was purified by combiflash (.12 g column) using hexanes, ethyl acetate, and 20% methanol in ethyl acetate to obtain (4R.,12aS)-N-(l-(2,4-difluoropheny].)cyclopropyl)-7-methoxy-4-methyi-6,8-dioxo- 3,4,6,8, 12, 12a-hexahydro-2H-[ l ,3]oxazino[3,2-d]pyrido[ l ,2-a]pyrazine-9-carboxamide, Intermediate 5-C. LCMS-ESI+ i n/z): | VI - H i calculated for C. l l.. ,: >VO: 460.17; found 460.2.
  • 2
  • [ 89793-12-4 ]
  • [ 1186663-18-2 ]
  • ethyl 2-((1-(2,4-difluorophenyl)cyclopropyl)amino)pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.9% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 12h; 105.2 Synthesis of ethyl 2-((1-(2,4-difluorophenyl)cyclopropyl)amino)pyrimidine-5-carboxylate In step 1 Manufactured 1-(2,4-difluorophenyl)cyclopropan-1-amine hydrochloride (0.200 g, 0.973 mmol), ethyl 2-chloropyrimidine-5-carboxylate (0.191 g, 1.021 mmol) and N,N-diisopropylethylamine (0.424 mL, 2.432 mmol) was dissolved in 1,4-dioxane (5 mL) at 90 °C and stirred at the same temperature for 12 hours, and then the temperature was lowered to room temperature to terminate the reaction. The solvent was distilled off under reduced pressure and the concentrate was purified by column chromatography (SiO2, 24 g cartridge; ethyl acetate / hexane = 10% to 50%) to give the title compound (0.217 g, 69.9% Was obtained in the form of a white solid.
  • 3
  • [ 3939-09-1 ]
  • [ 925-90-6 ]
  • [ 1186663-18-2 ]
YieldReaction ConditionsOperation in experiment
21.1% <strong>[3939-09-1]2,4-difluorobenzonitrile</strong> (5.000 g, 35.945 mmol) and titanium isoproxoxide (13.835 mL, 46.729 mmol) was dissolved in 2-methoxy-2-methylpropane (MTBE, 60 mL) at -20 C then ethyl magnesium bromide (1.00 Msolution in THF, 82.674 mL, 82.674 mmol) was added and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added borontrifluoride diethyl etherate (8.873 mL, 71.891 mmol) was added and the mixture was further stirred at room temperature for 12 hours. Then, sodium hydroxide (3.00 M solution in water, 35.945 mL, 107.836 mmol) was added to the reaction mixture at room temperature and the reaction was terminated by stirring for 30 minutes . The reaction mixture was filtered through a pad of celite to remove the solid. The saturated aqueous sodium chloride solution was poured into the filtrate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. To the concentrate was added hydrochloric acid (20 mL) and hexane (10 mL) and stirred, and the precipitated solid was filtered, washed with ethyl acetate and dried to give the title compound (1.559 g, 21.1%) as a white solid.
  • 4
  • [ 1235406-85-5 ]
  • [ 1186663-18-2 ]
  • 5-chloro-4-((1-(2,4-difluorophenyl)cyclopropyl)amino)-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / dimethyl sulfoxide / 18 h / 75 °C 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C
  • 5
  • [ 1235406-85-5 ]
  • [ 1186663-18-2 ]
  • C23H21ClF3N3O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In dimethyl sulfoxide at 75℃; for 18h; 224 Example 224 Synthesis of 5-chloro-4-((1-(2,4-difluorophenyl)cyclopropyl)amino)-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide To a solution of tert-butyl ((5-chloro-2,4-difluorophenyl)sulfonyl)(thiazol-4-yl)carbamate (0.250 g, 0.543 mmol) in anhydrous dimethyl sulfoxide (5 mL) was added 1-(2,4-difluorophenyl)cyclopropan-1-amine hydrochloride (0.223 g, 0.543 mmol) and cesium carbonate (0.792 g, 2.49 mmol). The resulting suspension was stirred at 75° C. for 18 h. After cooling toe ambient temperature, the mixture was diluted with ethyl acetate (5 mL) and water (5 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (3×3 mL). The combined organic phase was washed with brine (1×5 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo provided a residue which was dissolved in dichloromethane (10 mL). To it was added trifluoroacetic acid (1 mL) and the mixture was stirred at ambient temperature for 18 h. The solution was concentrated in vacuo and the obtained residue purified by column chromatography, eluting with a gradient of 5 to 80% of ethyl acetate in hexanes. Further purification by preparative reverse phase HPLC, using acetonitrile in water containing 0.1% trifluoroacetic acid as eluent, afforded the title compound as a colorless solid (0.014 g, 4% yield): 1H-NMR (300 MHz, DMSO-d6) δ 11.16 (s, 1H), 8.87 (d, J=2.2 Hz, 1H), 7.68 (td, J=8.9, 6.7 Hz, 1H), 7.59 (d, J=7.3 Hz, 1H), 7.34 (d, J=1.4 Hz, 1H), 7.19 (ddd, J=11.6, 9.2, 2.5 Hz, 1H), 7.07-7.01 (m, 1H), 6.98 (d, J=2.1 Hz, 1H), 6.80 (d, J=12.9 Hz, 1H), 1.39-1.34 (m, 2H), 1.27-1.24 (m, 2H); MS (ES+) m/z 460.0 (M+1), 462.0 (M+1).
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