Cat.NO.:A270417 Purity:97%
Product Details of [ 1001414-56-7 ]
CAS No. : | 1001414-56-7 |
Formula : |
C5H7BrClNS |
M.W : |
228.54
|
SMILES Code : | NCC1=CC=C(Br)S1.[H]Cl |
MDL No. : | MFCD08752581 |
InChI Key : | DWYVWUCEDHIAMH-UHFFFAOYSA-N |
Pubchem ID : | 42888202 |
Safety of [ 1001414-56-7 ]
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Computational Chemistry of [ 1001414-56-7 ] Show Less
Physicochemical Properties
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.66 |
TPSA ?
Topological Polar Surface Area: Calculated from |
54.26 Ų |
Lipophilicity
Log Po/w (iLOGP)?
iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)?
XLOGP3: Atomistic and knowledge-based method calculated by |
2.32 |
Log Po/w (WLOGP)?
WLOGP: Atomistic method implemented from |
2.62 |
Log Po/w (MLOGP)?
MLOGP: Topological method implemented from |
1.63 |
Log Po/w (SILICOS-IT)?
SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.83 |
Consensus Log Po/w?
Consensus Log Po/w: Average of all five predictions |
1.88 |
Water Solubility
Log S (ESOL):?
ESOL: Topological method implemented from |
-3.06 |
Solubility | 0.197 mg/ml ; 0.000864 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Log S (Ali)?
Ali: Topological method implemented from |
-3.1 |
Solubility | 0.182 mg/ml ; 0.000798 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)?
SILICOS-IT: Fragmental method calculated by |
-2.57 |
Solubility | 0.619 mg/ml ; 0.00271 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Pharmacokinetics
GI absorption?
Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant?
BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate?
P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor?
Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor?
Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor?
Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor?
Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor?
Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)?
Skin permeation: QSPR model implemented from |
-6.05 cm/s |
Druglikeness
Lipinski?
Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose?
Ghose filter: implemented from |
None |
Veber?
Veber (GSK) filter: implemented from |
0.0 |
Egan?
Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge?
Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score?
Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
Medicinal Chemistry
PAINS?
Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk?
Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness?
Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility?
Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.24 |
Application In Synthesis of [ 1001414-56-7 ]
* 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 [ 1001414-56-7 ]
[ 1001414-56-7 ] Synthesis Path-Downstream 1~7
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; In ethyl acetate; for 2.0h; | Reactamt (8.322 g, 0.0285 mmol) was dissolved in 150 ml of anhydrous ethyl acetate. The dried HCl was induced continuously for two hours and a large amount of precipitate formed. The solvent was removed and the residue was washed with anhydrous ethyl acetate (3 x 50 ml), ether (3 x 50 ml) in turn to give the product 01-0034-1 (5.862 g), yield: 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In ISOPROPYLAMIDE; at 20.0℃; for 24.0h; | 21H. 4-(Aminomethv?-N-((5-bromothiophen-2-v?methv?-l-(7H-pyrrolor2.3- dlpyrimidin-4-yl)piperidine-4-carboxamide; <n=”133″/>HATU (419 mg, 1.10 mmol) was added in one portion to 4-((diphenylmethylene- amino)methyl)- 1 -(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (440mg, 1.00 mmol), <strong>[1001414-56-7](5-bromothiophen-2-yl)methanamine hydrochloride</strong> (229 mg, 1.00 mmol) and DIPEA (0.699 mL, 4.00 mmol) in DMA (5 ml) at 2O0C under nitrogen. The resulting solution was stirred at 20 0C for 24 hours. The reaction mixture was diluted with EtOAc (100 mL), and washed sequentially with water (2 x 100 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford N-((5-bromothiophen- 2-yl)methyl)-4-((diphenylmethyleneamino)methyl)-l-(7H-pyrrolo[2,3-d]pyrimidin-4- yl)piperidine-4-carboxamide. The product was dissolved in IPA (5.00 ml), water (1 ml) and hydrogen chloride 6N in isopropanol (1.669 ml, 10.01 mmol). The solution was stirred at 20 0C for 24 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7MNH3/MeOH and pure fractions were evaporated to dryness. The crude gum was triturated with Et20 to give a solid which was collected by filtration and dried under vacuum to give 4-(aminomethyl)-N-((5-bromothiophen-2-yl)methyl)-l-(7H-pyrrolo[2,3-d]pyrimidin-4- yl)piperidine-4-carboxamide (134 mg, 29.8 %) as a white solid. IH NMR (400.13 MHz, DMSO-d6) delta 1.44 – 1.51 (2H, m), 1.79 (2H, s), 2.07 – 2.10 (2H, m), 2.66 (2H, s), 3.40 (2H, d), 4.28 (2H, q), 4.42 (2H, d), 6.56 (IH, d), 6.82 (IH, d), 7.03 (IH, d), 7.15 (IH, d), 8.12 (IH, s), 8.71 (IH, t), 11.62 (IH, s) MS m/e MH+ 451 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 16.0h; | Step 1 : N-((5-Bromothiophen-2-yl)methyl)-l-phenylmethanesulfonamide To a suspension of <strong>[1001414-56-7](5-bromo-2-thienyl)methanamine hydrochloride</strong> (2 g, 8.75 mmol) in dichloromethane (30 mL) was added N,N-diisopropylethylamine (3.2 mL, 18.4 mmol) and the reaction was stirred until complete dissolution. Phenylmethanesulfonyl chloride (1.75 g, 9.18 mmol) was then added and the reaction was stirred at ambient temperature for 16 hours. The reaction was diluted with dichloromethane and washed with water and brine, dried with MgS04, concentrated and purified by silica gel column chromatography (0-100% EtOAc in heptane) to give N-[(5-bromo-2-thienyl)methyl]-l-phenyl-methanesulfonamide (2.55 g, 84% yield). LCMS (m/z) ES+ 364 [M+18]+. |
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