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CAS No. : | 3685-23-2 | MDL No. : | MFCD00191730 |
Formula : | C7H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 143.18 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 38.13 |
TPSA : | 63.32 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.73 cm/s |
Log Po/w (iLOGP) : | 1.15 |
Log Po/w (XLOGP3) : | -2.19 |
Log Po/w (WLOGP) : | 0.59 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 0.18 |
Consensus Log Po/w : | 0.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.72 |
Solubility : | 748.0 mg/ml ; 5.22 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.39 |
Solubility : | 3530.0 mg/ml ; 24.6 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.08 |
Solubility : | 120.0 mg/ml ; 0.839 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.13 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
64.286 % ee | With 5% active carbon-supported ruthenium; hydrogen; sodium hydroxide In water at 100℃; for 20 h; Autoclave | p-Aminobenzoic acid (10.0 g, 0.07mol, leq.), 5 percent Ru/C (2,50 g) and 10percent NaOH (lOO.OmL) were mixed in autoclave. The mixture was stirred at 100°C under 15 bar of hydrogen. After 20h of stirring no Starting material was observed on TLC (DCM/MeOH/NH3 = 5/5/1, v/v/v, stain: ninhydrine). According to the NMR - full conversion and cis:trans ratio = 1 :4.6 . Reaction was stopped. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 5% active carbon-supported ruthenium; hydrogen; sodium hydroxide; In water; at 100℃; under 11251.1 Torr; for 20h;Autoclave; | p-Aminobenzoic acid (10.0 g, 0.07mol, leq.), 5 percent Ru/C (2,50 g) and 10percent NaOH (lOO.OmL) were mixed in autoclave. The mixture was stirred at 100°C under 15 bar of hydrogen. After 20h of stirring no Starting material was observed on TLC (DCM/MeOH/NH3 = 5/5/1, v/v/v, stain: ninhydrine). According to the NMR - full conversion and cis:trans ratio = 1 :4.6 . Reaction was stopped. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; In acetonitrile-water; | (Step 1) Synthesis of methyl cis-4-(1-(tert-butoxycarbonyl)-(4S)-fluoro-(2S)-pyrrolidinylcarbonylamino)cyclohexanecarboxylate In acetonitrile-water (1:1, v/v, 60 ml) was dissolved <strong>[3685-23-2]cis-4-aminocyclohexanecarboxylic acid</strong> (1.32 g, 9.22 mmol). To the resulting solution were added di-tert-butyl dicarbonate (2.05 g, 9.39 mmol) and triethylamine (2.39 ml, 9.07 mmol) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was acidified with 1N HCl, followed by extraction with a chloroform-methanol (5:1, v/v) mixture. The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby cis-4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid (2.30 g, 97%) was obtained as a white crystalline powder. |
73% | With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; | To a stirred solution of the commercially available 11a (286 mg, 2.0 mmol) in 2:1 1,4-dioxane-H2O (6 mL) at 0 C was added 1 M NaOH (3 mL), followed by di-tert-butyldicarbonate (480 mg, 2.2 mmol) dissolved in a minimal amount of 1,4-dioxane. The solution was stirred for 3 h and slowly warmed to room temperature, and was then concentrated in vacuo to obtain a white solid. The solid was dissolved in H2O (4 mL) and ethyl acetate (7 mL) and acidified to pH 1.5 using 1 M HCl, prompting precipitation of 12a. Compound 12a was collected by filtration (white solid, 388 mg, 73% yield) and was >95% pure by HPLC. 1H NMR (500 MHz, DMSO): delta 12.07 (s, 1H, br), 6.75 (s, 1H, br), 2.36 (m, 1H), 1.86 (m, 2H), 1.50-1.37 (m, 7H), 1.37 (s, 9H). |
47% | Synthesis of Compound 418:; c/s-4-ter^-Butoxycarbonylamino-cyclohexanecarboxylic acid (293); Cis-4-aminocyclohexane carboxylic acid (500 mg, 3.5 mmol) was dissolved in THF (10 mL). 2M sodium hydroxide solution (3.5 mL, 7.0 mmol) was added and the mixture cooled on ice before adding di-/ert-butyl dicarbonate (840 mg, 3.9 mmol). The reaction was warmed to RT and left stirring overnight before washing with TBME. The aqueous was acidified with IM KHSO4 solution and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and reduced in vacuo to leave the title compound.Yield: 401 mg (47%)1H NMR deltaH ppm (250 MHz, D4-MeOD): 3.49 (IH, m), 2.49 (IH, m), 2.07 - 1.91 (2H, m), 1.77 - 1.51 (6H, m), 1.46 (9H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | To a suspension of cw-4-aminocyclohexanecarboxylic acid (165 mg, 1.15 mmol) in CH2Cl2 (6 mL) was added thionyl chloride (0.25 mL, 3.4 mmol) and the resulting mixture was stirred at room temperature for 45 minutes. The solvent was removed and the residue was dried under reduced pressure. Methanol (6 mL) was added and the solution was stirred at reflux for 2 hours. Standard work-up gave the crude methyl cis-A- aminocyclohexanecarboxylate as a yellow liquid (121 mg, 67%). 1H NMR (CDCl3) delta 1.25 (s, 2H), 1.30-1.41 (m, 2H), 1.52-1.70 (m, 4H), 1.94-2.05 (m, 2H), 2.41-2.49 (m, IH), 2.78-2.87 (m, IH), 3.66 (s, 3H). | |
With thionyl chloride; | The amino acid (22.45 mmol, 1.0 eq) was suspended in MeOH (20 mL per 10 mmol of amino acid) and reaction mixture was cooled to 0 C. Thionyl chloride (4 eq) was carefully added dropwise and the reaction mixture was left to stir for 12h at room temperature. The mixture was concentrated under reduced pressure and diethylether was added (10 mL per 10 mmol of amino acid). Precipitate was collected and washed with cooled diethyether (10 mL per 10 mmol of amino acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; for 50h;Heating / reflux; | cis-4-Amino-1-cyclohexanecarboxylic acid (1.43 g, 10 mmol) was suspended in THF (30 mL) and triethylamine (1.31 mL, 9.5 mmol) was added, followed by benzoylisothio-cyanate (1.36 mL, 10 mmol). The mixture was heated to reflux for 2 h, cooled, and stirred for 48 h. Lithium hydroxide (1N aqueous solution, 20 mL, 20 mmol) was added, the mixture was heated to reflux for 1 h, and the mixture was then cooled to 25 C. 2-Bromo-1-(4-bromo-phenyl)-ethanone (2.78 g, 10 mmol) was added, the mixture was heated to reflux for 1 h, and the mixture was then cooled to 25 C. The mixture was diluted with water, acidified with 2N HCl, and extracted with ethyl acetate. The organics were combined and washed with brine, dried over MgSO4, and concentrated. Flashing with 25% acetone in hexane with 0.5% acetic acid gave the intermediate 4-[4-(4-bromo-phenyl)-thiazol-2-ylamino]-cyclohexanecarboxylic acid (0.38 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hydroxide; water; In tetrahydrofuran; for 2h;Heating / reflux;Product distribution / selectivity; | cis-4-Amino-1-cyclohexanecarboxylic acid (1.5 g, 10.5 mmol) was suspended in THF (40 mL), lithium hydroxide (1N aqueous solution, 10.5 mL, 10.5 mmol) was added, followed by benzoylisothiocyanate (1.42 mL, 10.5 mmol). The mixture was stirred for 30 min, lithium hydroxide (1N aqueous solution, 10.5 mL, 10.5 mmol) was added, and the mixture was heated to reflux for 1 h. Additional lithium hydroxide (1N aqueous solution, 0.3 mL, 0.3 mmol) was added, heating was continued for 30 min, and then the mixture was cooled to 25 C. 2-Bromo-1-(4-cyanophenyl)-ethanone (2.35 g, 10.5 mmol) was added, the mixture was heated to reflux for 1 h, and then concentrated. The crude product was chromatographed with 25% acetone in hexane with 0.5% acetic acid. Further chromatography with 20% acetone:20% ethyl acetate:60% hexane provided the intermediate 4-[4-(4-cyano-phenyl)-thiazol-2-ylamino]-cyclohexanecarboxylic acid (0.196 g, 0.609) that was dissolved in dioxane (30 mL). Carbonyl diimidazole (118 mg, 0.73 mmol) was added and the mixture was heated to 100 C. for 16 h. The mixture was concentrated and flashed with 10% acetone in hexane to give 105 mg of 4-[2-(3-oxo-2-azabicyclo[2.2.2]oct-2-yl)-1,3-thiazol-4-yl]benzonitrile. HPLC purity 100% at 210-370 nm, 10.0 min.; 100% at 244 nm, 10.0 min.; the Xterra RP18 instrument, 3.5mu, 150*4.6 mm column, 1.2 mu/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min. HRMS: calcd for C17H15N3OS+H+, 310.10086; found (ESI, [M+H]+), 310.1000. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(1 S,4S)-4-aminocyclohexanecarboxylic acid (5.11 g, 35.7 mmol) was added portionwise to a solution of BH3-THF (1 M, 214 mL) at room temperature. The suspension was stirred at room temperature overnight. MeOH (100 mL) was added slowly to the reaction at room temperature. After stirrnng for 2 h, the solvent was evaporated to give a clear oily residue. The crude oil residue was redissolved in MeOH (80 mL). The remaning excess BH3 was sca- vaged by stirring with Pd/C (10% wet, 250 mg) at room temperature for 60 h. The reaction mixture was filtered through a layer of celite, washed with MeOH and concentrated. The residue was dried further in vacuo. The crude product obtained was used for the next step without further purification. MS m/z 130.1 (M+H+) (Method M). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Step 2 Carboxylic acid 3 (5.66 g, 50.1 mmol) was suspended in 57 ml of methylene chloride, and oxalyl chloride (5.4 ml, 60.1 mmol) was added to the suspension. 4 drops of N,N-dimethylformamide was carefully added dropwise, and the mixture was stirred for 1 hour at room temperature.In another reaction vessel, cis-4-amino-1-cyclohexylcarbonic acid (8.6 g, 60.1 mmol) was suspended in 57 ml of 1,4-dioxane. 2N sodium hydroxide (60 ml, 120.2 mmol) and followed by a solution of methylene chloride obtained in the above step were added dropwise at 0 C., and the mixture was stirred overnight at room temperature. The reaction mixture was poured into 2N hydrochloric acid to acidify and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The resulting residue was suspended with heating, and the solution was allowed to stand at room temperature to yield carboxylic acid 4 (8.49 g, yield 71%) after filtration. 1H-NMR (DMSO-d6) delta: 1.53-1.72 (m, 6H), 1.97-2.03 (m, 2H), 2.52-2.53 (m, 1H), 3.82-3.90 (m, 1H), 6.90 (d, 1H, J=1.5 Hz), 8.58 (d, 1H, J=7.2 Hz), 9.07 (d, 1H, J=1.5 Hz), 12.17 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of cis-4-aminocyclohexanecarboxylic acid (1.5 equiv.), N,N- diisopropylethylamine (3.2 equiv.), and 1 -chloro-3-fluoro-2-nitro-benzene (1.0 equiv.) was stirred in MeOH at 120 C for 6 days. The mixture was poured into HCI (2 M) and extracted with DCMx3. The combined organics were dried and concentrated. The crude material was suspended in MeOH, then H2S04 (cone., 2.2 equiv.) was added carefully. The mixture was stirred at reflux for 20 h and was then poured into NaHC03 and extracted with DCM*3. The combined organics were dried, concentrated, and purified by silica gel chromatography which afforded methyl (cis)-4-(3-chloro-2-nitro- anilino)cyclohexanecarboxylate. LCMS [M+H]+ 313 |
Tags: 3685-23-2 synthesis path| 3685-23-2 SDS| 3685-23-2 COA| 3685-23-2 purity| 3685-23-2 application| 3685-23-2 NMR| 3685-23-2 COA| 3685-23-2 structure
[ 27960-59-4 ]
trans-4-Aminocyclohexanecarboxylic acid hydrochloride
Similarity: 0.97
[ 71830-08-5 ]
(1R,3S)-3-Aminocyclopentanecarboxylic acid
Similarity: 0.93
[ 74316-27-1 ]
cis-3-Aminocyclobutanecarboxylic acid
Similarity: 0.93
[ 854214-59-8 ]
4-Aminobicyclo[2.2.2]octane-1-carboxylic acid hydrochloride
Similarity: 0.90
[ 84182-59-2 ]
cis-3-Aminocyclobutanecarboxylic acid hydrochloride
Similarity: 0.90
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