Structure of 149423-70-1
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 149423-70-1 |
Formula : | C14H20N2O2 |
M.W : | 248.32 |
SMILES Code : | O=C(OCC1=CC=CC=C1)N[C@H]2CC[C@@H](N)CC2 |
MDL No. : | MFCD06657668 |
InChI Key : | JQVBZZUMWRXDSQ-UHFFFAOYSA-N |
Pubchem ID : | 18650082 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 70.13 |
TPSA ? Topological Polar Surface Area: Calculated from | 64.35 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.54 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.68 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.45 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.9 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.45 |
Solubility | 0.883 mg/ml ; 0.00356 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.8 |
Solubility | 0.392 mg/ml ; 0.00158 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.4 |
Solubility | 0.1 mg/ml ; 0.000403 mol/l |
Class? Solubility class: Log S scale | Soluble |
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 | -6.52 cm/s |
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 |
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) | 3.01 |
* 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 |
---|---|---|
53% | With IEA; In isopropyl alcohol; at 170.0℃; for 5.0h; | To a solution of <strong>[149423-70-1]cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester</strong> (0.5 g, 0.0020 mol) in 1 ml_ 2-propanol was added 2-chloro-4-methyl-quinoline (0.43 g, 0.0024 mol) and IEA (526 uL, 0.0030 mol). The mixture was heated in a microwave synthesizer at 170 C for 5 hours. The reaction was repeated 7 more times (4 g total material) and the reaction mixtures were pooled. The solvent was evaporated and the material subjected to chromatography (2-4 % 2M NH3 in MeOH / CH2Cl2) to yield cis-[4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-carbamic acid benzyl ester (3.3 g, 53%) as a colorless oil. ESI MS m/e 390.2 M + H+; 1H NMR (400 MHz, DMSO-d6) delta 7.71 (d, J = 8 Hz, 1 H), 7.46-7.39 (m, 2 H), 7.37-7.19 (m, 7 H), 6.68 (m, 2 H), 5.01 (s, 2 H), 4.07 (m, 1 H), 3.46 (m, 1 H), 2.44 (s, 3 H), 1.79-1.71 (m, 2 H), 1.70-1.59 (m, 6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With trifluoroacetic acid; In dichloromethane; at 20.0℃; for 4.0h; | Step B: Synthesis of cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester. To a solution of cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (6.2 g, 0.018 mol) in 40 mL CH2Cl2 was added TFA (2.7 mL, 0.36 mol). The solution was stirred at room temperature for 4 hours. The excess solvent was evaporated off and the resulting oil was dissolved in 30 mL CH2Cl2. The organic layer was extracted with 30 mL of a dilute NaOH (aq) / NaHCO3 (aq) solution. The aqueous layer was back extracted twice with CH2Cl2 and the organic layers combined, dried over MgSO4, and concentrated to yield cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester (4.3 g, 97%) as a colorless oil. The oil was carried forward without further purification. ESI MS m/e 249.2 M + H+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20.0℃; for 20.0h; | To a mixture of 2,4-dichloro-5-fluoropyrimidine (226 mg, 1.35 mmol) and benzyl (ls,4s)-4-aminocyclohexylcarbamate (335 mg, 1.35 mmol) in CH3CN (6 mL), DIEA (0.600 mL, 3.45 mmol) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. The organic phase was separated, washed with IN HCl, dried over Na2SO4, concentrated in vacuo to give benzyl (ls,4s)-4-(2-chloro-5-fluoropyrimidin-4- ylamino)cyclohexylcarbamate (511 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20.0℃; for 20.0h; | To a mixture of 2,4-dichloro-5-bromopyrimidine (244 mg, 1.07 mmol) and benzyl (ls,4s)-4-aminocyclohexylcarbamate (266 mg, 1.07 mmol) in CH3CN (5 mL), DIEA (0.373 <n="192"/>mL, 2.14 mmol) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. The organic phase was separated, washed with IN HCl, then with 5% NaHCCbeta, dried over Na2SO4, concentrated in vacuo to give benzyl (ls,4s)-4-(5-bromo-2- chloropyrimidin-4-ylamino)cyclohexylcarbamate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; triphenylphosphine; In tetrahydrofuran; at 70.0℃; for 20.0h; | To a solution of benzyl (ls,4s)-4-azidocyclohexylcarbamate (0.410 g, 1.50 mmol) in THF (8 mL) and H2O (0.100 mL, 5.56 mmol) at room temperature, Ph3P (0.590 g, 2.25 mmol) was added. The solution was stirred at 7O0C for 20 h. EtOAc and IN HCl were added. The aqueous phase was separated, washed with EtOAc. It was then basified with 5N NaOH to pH 12. The free amine product was extracted with EtOAc. The EtOAc solution was dried over Na2SO4, and concentrated in vacuo to give benzyl (ls,4s)-4-aminocyclohexylcarbamate (0.270 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.47 g | In dichloromethane; for 1.0h; | Amine D1.1 (Prepared as described in Bauer, Shawn M.; Jia, Zhaozhong J.; Song, Yonghong; Xu, Qing; Mehrotra, Mukund; Rose, Jack W.; Huang, Wolin; Venkataramani, Chandrasekar; Pandey, Anjali. PCT mt. Appi. (2009), W02009145856A1.) (1.92 g, 7.7 mmol) was diluted with dichioromethane (30 mL) affording an opaque solution. To this was added di-tbutyl dicarbonate (2.0 g, 9.3 mmol) in two portions. The resulting solution was then stirred for approximately 1 hr at which time the reaction was determined to be complete by UPLC. The reaction mixture was then concentrated and dried in vacuo overnight affording 2.47 g of the diprotected diamine as a light pink syrup. MS found for C11H21N202 as (M - Boc+2H) 249.2 and (M+Na)+ = 371.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; In water; for 4.0h;Reflux; | A solution of (±)-cis-1-N-cbz-1 ,4-cyclohexyldiamine (500 mg, 2.0 mmol, 1 eq.) in formaldehyde (36.5% in H20, 15 mL) and formic acid (0.25 mL, 6.6 mmol, 3.3 eq.) was heated at reflux for 4 hours. The mixture was allowed to cool to r.t. and poured into a sat. NaHC03 soln. (50 mL). The mixture was extracted with AcOEt (3 x 30 mL). The comb. org. phases were dried over MgS04 and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters X-Bridge, 30x75 mm, 10 muetaiota, UV/MS, basic conditions) to give (±)-cis-(4-dimethylamino-cyclohexyl)-carbamic acid benzyl ester as a white solid. LC-MS 3: tR = 0.82 min; [M+H]+ = 277.0 |
Tags: 149423-70-1 synthesis path| 149423-70-1 SDS| 149423-70-1 COA| 149423-70-1 purity| 149423-70-1 application| 149423-70-1 NMR| 149423-70-1 COA| 149423-70-1 structure
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