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CAS No. : | 453562-69-1 | MDL No. : | MFCD10567689 |
Formula : | C22H23N5O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RAHBGWKEPAQNFF-UHFFFAOYSA-N |
M.W : | 373.45 | Pubchem ID : | 11667893 |
Synonyms : |
AMG 706
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.23 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 114.63 |
TPSA : | 78.94 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.83 cm/s |
Log Po/w (iLOGP) : | 2.82 |
Log Po/w (XLOGP3) : | 3.87 |
Log Po/w (WLOGP) : | 2.94 |
Log Po/w (MLOGP) : | 2.11 |
Log Po/w (SILICOS-IT) : | 3.43 |
Consensus Log Po/w : | 3.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.67 |
Solubility : | 0.00793 mg/ml ; 0.0000212 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.22 |
Solubility : | 0.00223 mg/ml ; 0.00000596 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.45 |
Solubility : | 0.00000132 mg/ml ; 0.0000000035 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; | N-[3,3-Dimethyl-1-(1-oxy-pyridine-4-carbonyl)-2,3-dihydro-1H-indol-6-yl]-2-[(pyridin-4-ylmethyl)-amino]-nicotinamide To a solution of <strong>[453562-69-1]N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)-amino]-nicotinamide</strong> (374 mg, 1 mmol) in a mixture of DCM (20 mL) and DMF (10 mL) were added EDC (400 mg, 2 mmol), HOBt (80 mg) and DIEA (0.5 mL). The reaction mixture was stirred at RT overnight. After removing solvents in vacuo, the residue was suspended in water. The mixture was sonicated for 5 min and a precipitation was received after filtration. The filter cake was washed with water and then dried in a vacuum oven at RT. The dried solid was then purified via preparative TLC on silica gel (DCM:EtOH:TEA=100:3:6) to afford the desired product. MS: (ES+) 495 (M+H). Calc'd. for C28H26N6O3-494.54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 20℃; | EXAMPLE 1100 N-[3,3-Dimethyl-1-(1-oxy-pyridine-4-carbonyl)-2,3-dihydro-1H-indol-6-yl]-2-[(pyridin-4-ylmethyl)-amino]-nicotinamide To a solution of <strong>[453562-69-1]N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)-amino]-nicotinamide</strong> (374 mg, 1 mmol) in a mixture of DCM (20 mL) and DMF (10 mL) were added EDC (400 mg, 2 mmol), HOBt (80 mg) and DIEA (0.5 mL).The reaction mixture was stirred at RT overnight. After removing solvents in vacuo, the residue was suspended in water.The mixture was sonicated for 5 min and a precipitation was received after filtration.The filter cake was washed with water and then dried in a vacuum oven at RT. The dried solid was then purified via preparative TLC on silica gel (DCM:EtOH:TEA=100:3:6) to afford the desired product. MS: (ES+) 495 (M+H). Calc'd. for C28H26N6O3-494.54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
This compound was prepared via standard reductive amination conditions of <strong>[453562-69-1]N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)-amino]-nicotinamide</strong> with 1-oxy-pyridine-4-carbaldehyde, as previously described. MS: (ES+) 481 (M+H) Calc'd. for C28H28N6O2-480.56. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step C-Preparation of N-(3,3-dimethylindolin-6-yl){2-[(4-pyridylmethyl)amino](3-pyridyl)}carboxamide The titled compound was prepared from N-(1-acetyl-3,3-dimethylindolin-6-yl){2-[(4-pyridylmethyl)amino](3-pyridyl)}carboxamide (Step B) by the deacylation method described in Example 993. MS: 374 (M+1). Calc'd. for C22H23N5O-373.45. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | 21 a: 3,3-Dimethyl-N-((2-(pyridin-4-ylmethylamino)pyridin-3-yl)methyl)indolin-6-amine To a solution of BH3-Me2S (1 M in THF, 10 mL, 10 mmol, 12.5 eq) was added intermediate B (300 mg, 0.8 mmol, 1 .0 eq) at 0 C under nitrogen. The mixture was allowed to warm to room temperature, stirred for 1 h then heated at reflux for 48 h. After cooling to 0 C, a 2 M aqueous HCI solution (20 mL) was added dropwise and the mixture was heated at 70 C for 3 h then cooled to room temperature and washed with EtOAc (15 mL x 3). The aqueous layer was basified to pH 8-9 with a 3 M aqueous NaOH solution and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine, dried over Na2S04 and the solvent was removed under reduced pressure. The residue was purified by column chromatography (EtOAc/Pet. ether, 1/100 to 1/5, v/v) to give a light yellow sticky oil, which was further purified by preparative TLC (EtOAc/Pet. ether, 1/2, v/v) to give 3,3-dimethyl-N-((2-(pyridin-4- ylmethylamino)pyridin-3-yl)methyl)indolin-6-amine (22 mg, 8%) as a pale yellow solid.LC-MS (Agilent): Rt 3.19 min; m/z calculated for C22H25N5 [M+H]+ 360.47, found 360.2.1H NMR: (400 MHz, DMSO-d6) delta (ppm): 8.93 (br s, 3H), 8.09 (br s, 2H), 7.84 (m, 2H), 7.14 (d, J = 8.0 Hz, 1 H), 6.91 (m, 1 H), 6.69 (d, J = 8.0 Hz, 1 H), 6.61 (s, 1 H), 5.18 (s, 2H), 4.37 (s, 2H), 3.38 (s, 3H), 3.17 (s, 1 H), 1 .29 (s, 6H). | |
8% | To a solution of BH3.Me2S (1 M in THF, 10 mL, 10 mmol, 12.5 eq) was added intermediate B (300 mg, 0.8 mmol, 1.0 eq) at 0 C. under nitrogen. The mixture was allowed to warm to room temperature, stirred for 1 h then heated at reflux for 48 h. After cooling to 0 C., a 2 M aqueous HCl solution (20 mL) was added dropwise and the mixture was heated at 70 C. for 3 h then cooled to room temperature and washed with EtOAc (15 mL*3). The aqueous layer was basified to pH 8-9 with a 3 M aqueous NaOH solution and extracted with EtOAc (20 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography (EtOAc/Pet. ether, 1/100 to 1/5, v/v) to give a light yellow sticky oil, which was further purified by preparative TLC (EtOAc/Pet. ether, ½, v/v) to give 3,3-dimethyl-N-((2-(pyridin-4-ylmethylamino)pyridin-3-yl)methyl)indolin-6-amine (22 mg, 8%) as a pale yellow solid. LC-MS (Agilent): Rt 3.19 min; m/z calculated for C22H25N5 [M+H]+ 360.47. found 360.2. 1H NMR: (400 MHz, DMSO-d6) delta (ppm): 8.93 (br s, 3H), 8.09 (br s, 2H), 7.84 (m, 2H), 7.14 (d, J=8.0 Hz, 1H), 6.91 (m, 1H), 6.69 (d, J=8.0 Hz, 1H), 6.61 (s, 1H), 5.18 (s, 2H), 4.37 (s, 2H), 3.38 (s, 3H), 3.17 (s, 1H), 1.29 (s, 6H). |
A238109[ 857876-30-3 ]
N-(3,3-Dimethylindolin-6-yl)-2-((pyridin-4-ylmethyl)amino)nicotinamide diphosphate
Reason: Free-salt