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CAS No. : | 279236-52-1 | MDL No. : | MFCD20638954 |
Formula : | C8H14N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UHCZEASPZTXWPC-UHFFFAOYSA-N |
M.W : | 186.21 | Pubchem ID : | 18722251 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.34 |
TPSA : | 83.63 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) : | -7.87 cm/s |
Log Po/w (iLOGP) : | 0.92 |
Log Po/w (XLOGP3) : | -0.61 |
Log Po/w (WLOGP) : | -0.13 |
Log Po/w (MLOGP) : | 0.12 |
Log Po/w (SILICOS-IT) : | -0.65 |
Consensus Log Po/w : | -0.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.41 |
Solubility : | 72.1 mg/ml ; 0.387 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.67 |
Solubility : | 39.4 mg/ml ; 0.212 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.26 |
Solubility : | 336.0 mg/ml ; 1.8 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.31 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 22℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 22℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 120h; | 118 Example 118 [0330] A solution of the product from Preparative Example 33 (0.64 mmol), carboxamidopiperadineacetic acid (0.29 g, 1.3 eq.), DEC (0.17 g, 1.3 eq.), HOBt (0.12 g, 1.3 eq.), and NMM (0.36 mL, 5.0 eq.) in DMF (8.0 mL) was stirred at room temperature 5 days. The reaction was quenched by the addition of 1N NaOH and extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography using a 15% MeOH in CH2Cl2 solution as eluent (0.13 g, 42% yield); FABMS: MH+=471; mp=63-68° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With lithium hydroxide In ethanol; dichloromethane; water for 3h; Heating / reflux; | 24.C Step C A solution of the title compound from Preparative Example 24, Step B (1.23 g, 5.7 mmol) and LiOH (0.33 g, 2.4 eq.) in CH2Cl2 (29 mL), EtOH (29 mL) and water (14 mL) was heated at reflux 3 hours. The resulting solution was cooled to room temperature, neutralized by the addition of 1N HCl (16.1 mL, 2.98 eq.) and concentrated under reduced pressure. The reaction product was further dried by the azeotropic removal of water with toluene to yield an off-white gum (1.1 g, quantitative yield). FABMS: MH+=187. |
100% | With lithium hydroxide; water In ethanol; dichloromethane for 3h; Heating / reflux; | 55.C Step C [0321] A solution of the product from Step B above, (1.23 g, 5.7 mmol) and LiOH (0.33 g, 2.4 eq.) in CH2Cl2 (29 mL), EtOH (29 mL) and water (14 mL) was heated at reflux for 3 hours. The resulting solution was cooled to room temperature, neutralized by the addition of 1N HCl (16.1 mL, 2.98 eq.) and concentrated under reduced pressure. The reaction product was further dried by the azeotropic removal of water with toluene to yield a gum (1.1 g, quantitative yield). FABMS: MH+=187. |
Stage #1: (1-carbamoyl-piperidin-4-yl)-acetic acid ethyl ester With lithium hydroxide; water In ethanol; dichloromethane at 50℃; for 5h; Stage #2: With hydrogenchloride In ethanol; dichloromethane; water for 0.0833333h; | 21.C Step C [1991] Product from Step B above (40.63 mg; 0.1896 mmol) was taken up in EtOH (2 ml) and CH2Cl2 (2 ml) and treated with 1 M LiOH (0.5 ml; 0.455 mmol). The reaction mixture was heated to 50° C. and stirred for 5 hr. The reaction was cooled to room temperature treated with 1N HCl (0.57 ml; 0.531 mmol) and stirred for 5 minutes. The resultant mixture was concentrated and dried under high vacuum for 4 days affording the title compound as a white solid. (223) |
With lithium hydroxide; water In ethanol; dichloromethane at 50℃; for 5.5h; | 20 Ethyl 1-aminocarbonyl-4-piperidinyl acetate (153.6mg, 0.717mmoles) is dissolved in anhydrous CH2Cl2 (3.58mL) and EtOH (3.58mL). To the solution is added 1 0M LiOH (1.73mL, 1.73mmoles) and the mixture is stirred at 50°C for 5.5h. The mixture is cooled quickly to 25°C and 1.0N HCl (2.02mL, 2.02mmoles) is added and the mixture stirred for 5 minutes and then rotovapped to dryness to give the title compound which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 45h; | 30 Compound (20.3), isomer 2 (0.15g, 0.285mmoles) (prepared as described in Example 20 above), 1-(3-dimethyl-aminopropyl)-3~ethylcarbodiimide hydrochloride (0.0709g, 0.371 mmoles), 1-hydroxy-benzotriazole (0.05g, 0.371 mmoles) and 4- methylmorpholine (0.814mL, 0.741 mmoles) were dissolved in anhydrous DMF (1 mL) and 1-(carboxamido-piperidine)-4-acetic acid (0.0691 g, 0.371 mmoles) was added in anhydrous DMF (3ml_).The mixture was stirred at 25°C for 45h. and the reaction was then worked up as described in Preparative Example 6, Step A above. The product was chromatographed on silica gel using 6% (10% cone. NH4OH in methanol)- dichloromethane as the eluant to give compound (30.1) (0.1033g, 52%): FABMS: m/z 695.3 (MH+); HRFABMS: m/z 695.3234 (MH+). Calcd. C38H44N8O3CI: m/z 695.3225 (MH+); δH (CDCI3) 2.16 (3H, s, 4-CH3), 4.36 (1 H, s, CHCON), 4.83 (1 H, s, H11), 4.97 (2H, s, CH2-Im), 6.59 (1 H, s, Im-H5), 6.83 (1 H, d, Ar-H4.), 7.04-7.19 (5H, s and m, Ar- H), (7.27 (2H, dd, Ar-H3 and Ar-H5O, 7.37 (1 H, s, Im-H2), 7.41 (1 H, d, Ar-H4), 8.25 (1 H, d, Ar-H2) and 8.83ppm (1 H, bs, NHCO); δc (CDCI3) CH3: 13.7; CH2: 30.2, 30.8, 31.9, 32.0, 39.7, 44.1 , 44.3, 44.5, 50.7, 50.9, 52.6; CH: 32.9, 53.7, 78.7, 115.9, 118.2, 119.5/119.9, 123.0, 123.4, 126.1 , 129.5, 130.8, 132.4, 136.4, 139.3/139.4, 146.0; C: 134.1 , 135.6, 137.2, 137.2, 138.7, 139.1 , 141.4, 156.7,158.2, 168.7, 171.6, 172.4; [α]D20°c +74.6° (c= 0.50, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 66h; | 39 Compound (35.1), isomer 1 (silica gel) (0.14g, 0.273mmoles) (prepared as described in Example 35 above), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.068g, 0.355mmoles), 1-hydroxybenzotriazole (0.0479g, 0.355mmoles) and 4-methylmorpholine (0.039ml_, 0.355mmoles) were dissolved in anhydrous DMF (3mL) and 1-(carboxamido-piperidine)-4-acetic acid (0.0661 g, 0.355mmoles) was added in anhydrous DMF (2ml_). The mixture was stirred at 25°C for 41 h. Additional 1-(carboxamidopiperidine)-4-acetic acid (0.0102g, 0.0546mmoles) was added. The reaction was allowed to proceed for a total of 66h. The reaction was then worked up as described in Preparative Example 6, Step A above. The product was chromatographed on silica gel using 3.5% (10% cone. NH4OH in methanol)- dichloromethane as the eluant to give compound (39.1) (0.1185g, 64%): FABMS: m/z 681.38 (MH+); HRFABMS: m/z 681.3066 (MH+), Calcd. C37H42N8O3 m/z 681.3068; δH (CDCI3) 4.35 (1 H, dd, CHCON), 5.14 (2H, s, CH2-Im), 5.30 (1 H, s, H11), 6.95 (1 H, d, Ar-H4'), 6.95 (1 H, s, Im-H5), 7.14 (1 H, s, Im-H4), 7.18 (1 H, s, Ar-H7), 7.15-7.42 (4H, m, Ar-H)1 7.47 (1 H, s, Ar-H2.), 7.54 (1 H, d, Ar-H6.), 7.68 (1 H, d, Ar-H4), 7.71 (1 H, s, Im- H2), 8.38 (1 H, d, Ar-H2) and 9.78/9.94ppm (1 H, s, NHCO); δc (CDCI3) (Principal rotamer) CH2: 30.7, 31.7, 32.0, 38.4, 42.0, 44.3, 44.7, 44.8, 50.7, 50.7; CH: 39.0, 58.4, 118.0, 119.0, 119.5, 123.0, 123.9, 126.7, 129.7, 130.7, 130.7, 132.8, 137.3, 137.5, 138.6, 140.2, 146.4; C: 73.5, 134.9, 135.4, 137.3, 141.4, 155.2, 158.2, 168.2, 170.9; [α]D25°c +76.1° (c= 0.51 , MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 166h; | 45 Compound (41.1), isomer 1 (silica gel) (0.0356g, 0.069mmoles) (prepared as described in Example 41 above), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.0173g, 0.09mmoles), 1-hydroxybenzotriazole (0.0122g, 0.09mmoles) and 4-methylmorpholine (0.0099ml_, 0.09mmoles) were dissolved in anhydrous DMF (1 mL) and 1-(carboxamidopiperidine)-4-acetic acid (0.0168g, 0.09mmoles) was added in anhydrous DMF (1 mL). The mixture was stirred at 250C for 166h. The reaction was then worked up as described in Preparative Example 6, Step A above. The product was chromatographed on silica gel using 3.5% (10% cone. NH4OH in methanol)- EPO dichloromethane as the eluant to give compound (45.1), isomer 1 (isomer 1 , silica gel)(0.014g, 30%): FABMS: m/z 681.2 (MH+); HRFABMS: m/z 681.3066 (MH+), Calcd. C37H42N8OS mZz 681.3068; δH (CDCI3) 4.35 (1 H, dd, CHCON), 5.14 (2H, s, CH2-Im), 5.30 (1 H, s, H11), 6.94 (1 H, d, Im-H5), 6.97 (1 H s, Ar-H4O, 7.11 (1 H, s, Ar-H7), &.15 (1 H, s, Im-H4), 7.15-7.42 (4H, m, Ar-H), 7.47 (1 H, s, Ar-H2-), 7.54 (1 H, d, Ar-H6'), 7.68 (1 H, d, Ar-H4), 7.69 (1 H, s, Im-H2), 8.38 (1 H, d, Ar-H2) and 9.77/9.93ppm (1 H, s, NHCO); δc (CDCI3) (Principal rotamer) CH2: 30.7, 31.7, 31.9, 38.4, 38.4, 42.0, 44.3, 44.8, 44.9, 50.8, 50.8; CH: 32.6, 39.0, 58.6, 118.0, 119.0, 119.6, 123.1 , 123.9, 126.8, 129.8, 130.8, 130.8, 132.9, 137.4, 137.5, 138.5, 140.2, 146.5; C: 73.5, 134.9, 135.3, 137.4, 141.4, 155.1 , 158.2, 168.2, 170.8; [α]D25°c -58.3° (c= 0.17, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 166h; | 46 Compound (42.1), isomer 2 (silica gel) (0.0912g, 0.178mmoles) (prepared as described in Example 42 above), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.0443g, 0.231 mmoles), 1-hydroxybenzotriazole (0.0312g, 0.231 mmoles) and 4-methylmorpholine (0.0254mL, 0.231 mmoles) were dissolved in anhydrous DMF (2ml_) and 1-(carboxamidopiperidine)-4-acetic acid (0.0431 g, 0.231 mmoles) was added in anhydrous DMF (2mL). The mixture was stirred at 25°C for 166h. The reaction was then worked up as described in Preparative Example 6, Step A above. The product was chromatographed on silica gel using 3.5% (10% cone. NH4OH in methanol)-dichloromethane as the eluant to give compound (46.1), isomer EPO 2 (isomer 2, silica gel) (0.059g, 49%): FABMS: m/z 681.3 (MH+); HRFABMS: m/z681.3066 (MH+), Calcd. C37H42N8O3 InZz 681.3068; δH (CDCI3) 4.30 (1 H, d, CHCON), 5.12 (2H, d, CH2-Im), 5.28/5.30 (1 H, s, H11), 6.92 (1 H, s, Im-H5), 6.94 (1 H, d, Ar-H4-), 7.10 (1 H, s, Ar-H7), 7.14-7.32 (6H, m, Ar-H and Im-H4), 7.36 (1 H, s, Ar-H2-), 7.41 (1 H, d, Ar-H6-), 7.60 (1 H, s, Im-H2), 8.33 (1 H, d, Ar-H2) and 9.30ppm (1 H, s NHCO); δc (CDCI3) (Principal rotamer) CH2: 31.2, 31.9, 32.0, 37.3, 40.4, 44.3, 44.5, 44.6, 50.7, 50.7; CH: 32.6, 38.9, 59.7, 117.7, 118.8, -119.6, 123.2, 123.7, 127.0, 129.8, 130.4, 130.4, 132.6, 137.5, 137.5, 138.3, 140.2, 146.8; C: 73.3, 134.7, 134.8, 137.5, 141.3, 155.0, 158.2, 169.1 , 171.0; [α]D25°C +80.0° (c= 0.23, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; LiOH In ethanol; dichloromethane | P.20 1-Aminocarbonyl-4-piperidinylacetic acid Preparative Example 20 1-Aminocarbonyl-4-piperidinylacetic acid Ethyl 1-aminocarbonyl-4-piperidinyl acetate (153.6 mg, 0.717 mmoles) is dissolved in anhydrous CH2Cl2 (3.58 mL) and EtOH (3.58 mL). To the solution is added 1.0M LiOH (1.73 mL, 1.73 mmoles) and the mixture is stirred at 50° C. for 5.5 h. The mixture is cooled quickly to 25° C. and 1.0N HCl (2.02 mL, 2.02 mmoles) is added and the mixture stirred for 5 minutes and then rotovapped to dryness to give the title compound which is used without further purification. |
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