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CAS No. : | 1242338-90-4 | MDL No. : | MFCD16817646 |
Formula : | C7H2ClF2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BRCVOCMSJCGQNR-UHFFFAOYSA-N |
M.W : | 173.55 | Pubchem ID : | 50998596 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.08 |
TPSA : | 23.79 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) : | -5.6 cm/s |
Log Po/w (iLOGP) : | 1.74 |
Log Po/w (XLOGP3) : | 2.47 |
Log Po/w (WLOGP) : | 3.33 |
Log Po/w (MLOGP) : | 2.9 |
Log Po/w (SILICOS-IT) : | 3.29 |
Consensus Log Po/w : | 2.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.88 |
Solubility : | 0.231 mg/ml ; 0.00133 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.61 |
Solubility : | 0.422 mg/ml ; 0.00243 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.65 |
Solubility : | 0.0385 mg/ml ; 0.000222 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
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: |
* 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 |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110.0℃; for 18.0h;Microwave irradiation; Sealed tube; Inert atmosphere; | Example 93 Preparation of Compound 93 (lR,4S,12aR)-N<2-chloro-4,6-dtf octahydro-l,4-methanodipyrido[l,2-a:r,2'-d]pyrazme-9-carboxarnide Step 1 A 5 mL microwave vial was charged with 2-bromo-l-chioro-3,5- difluorobenzene (540 mg, 2.4 mmol), cuprous cyanide (436 mg, 4,87 mmol), tetrakis(triphenylphosphme)palladium (63 mg, 0.05 mmol), sealed, and evacuated/backfilled with nitrogen. To this was added 5 mL degassed DMF. The sealed vessel was heated at 110 C for 18 hours, diluted with ethyl acetate, and washed sequentially with twice 9:1 NH40H:NH4Ci aq twice 5% LiCl(aq ), and brine. The organic phase was then dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash chromatography (100% hexanes) to afford 2-chloro-4,6- difiuorobenzonitrile. - MR (400 MHz, Chloroform-*/) delta 7.13 (dt, J ------- 8.0, 1.9 Hz, 1H), 6.93 (td, J = 8.5, 2.3 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / Reflux 1.2: 0.5 h / 0 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 1 h / 20 °C 3.1: trifluoroacetic acid / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-chloro-4,6-difluorobenzonitrile With dimethylsulfide borane complex In tetrahydrofuran for 18h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Reflux; | 93.2 Step 2 Step 2 To a solution of 2-chloro-4,6-difluorobenzonitrile (210 mg, 1.2 mmol) in 2.4 mL THF was added a 2M solution of borane-DMS in THF (0.6 mL). This reaction mixture was allowed to stir at refiuxing temperature for 18 hours resulting in a loss of all solvent. The residue was re-dissolved in 3 mL THF, cooled to 0 °C, a 6M solution of HCl(aq) was carefully added, and the mixture returned to reflux for 30 minutes. The reaction mixture was once again cooled to 0 °C and treated with 4M NaOH(an . The aqueous phase was extracted with DCM, combined organic phases dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash chromatography (0-10% MeQH/DCM) to afford (2-chloro-4,6~ difluorophenyl)methanamine. ^l-N R (400 MHz, Chloroform-*/) 6 6.95 (dt, ,/ 8.3, 2.1 Hz, 1 1 1 ). 6.76 (td, ./ 9.4, 2,5 Hz, I I I }. 3.94 id. J 1 .9 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / Reflux 1.2: 0.5 h / 0 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: 2-chloro-4,6-difluorobenzonitrile With lithium dipropan-2-ylazanide In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran for 0.5h; | 87.1 Step 1: 6-chloro-2,4-difluoro-3-(triethylsilyl)benzonitrile To a solution of 2-chloro-4,6-difluorobenzonitrile (100 mg, 0.6 mmol) dissolved in THF (2 ml) under Ar and cooled to -78°C was added LDA (0.3 ml, 0.7 mmol) and the mixture stirred for 5 min after which time chlorotrimethylsilane ( 0.1 ml, 0.6 mmol) was added and the reaction stirred for a further 30 min. The reaction was quenched by addition of saturated aqueous ammonium chloride, allowed to reach ambient temperature, extracted with ethyl acetate, dried (Na2SO4) and concentrated. Flash column chromatography (heptane) afforded the title compound (127 mg, 73%) as a colourless oil. 1HNMR (CHLOROFORM-d, 300 MHz) δ 7.03 (dd, 1H, J=1.4, 8.1 Hz), 0.9-1.0 (m, 15H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium dipropan-2-ylazanide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 1.2: 0.5 h 2.1: lithium dipropan-2-ylazanide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: -78 °C |
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