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CAS No. : | 622867-52-1 | MDL No. : | MFCD12408124 |
Formula : | C15H21NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VVTNAXCVGQIIOV-UHFFFAOYSA-N |
M.W : | 263.33 | Pubchem ID : | 59132278 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.53 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 77.75 |
TPSA : | 49.77 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.66 cm/s |
Log Po/w (iLOGP) : | 3.11 |
Log Po/w (XLOGP3) : | 1.75 |
Log Po/w (WLOGP) : | 1.79 |
Log Po/w (MLOGP) : | 1.93 |
Log Po/w (SILICOS-IT) : | 2.33 |
Consensus Log Po/w : | 2.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.54 |
Solubility : | 0.751 mg/ml ; 0.00285 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.41 |
Solubility : | 1.02 mg/ml ; 0.00387 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.29 |
Solubility : | 0.134 mg/ml ; 0.000507 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.36 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
99.3% | Stage #1: With borane-THF In tetrahydrofuran at 25℃; for 16 h; Inert atmosphere Stage #2: With sodium carbonate In tetrahydrofuran; water for 0.25 h; |
Example 16 Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (D-1) To a solution of 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester (12.50 g, 45.08 mmol) in dry THF (125.0 mL), under nitrogen at 25° C., is added via syringe borane THF complex (99.17 mL, 99.17 mmol) The mixture is stirred at 25° C. for 16 h then water (10.0 mL) is slowly added followed by 2.0 M Na2CO3 (15.0 mL). This mixture is stirred for 15 min and then is diluted with EtOAc and the organic layers are collected. The organics are rinsed with 1M HCl, dried over MgSO4, and concentrated under reduced pressure to afford an oil. The oil is purified by silica gel chromatography to yield D-1-1 (11.8 g, 99.3percent yield), as a white solid. To a solution of alcohol, D-1-1, (9.50 g, 36.1 mmol) and N,N-diisopropylethylamine (9.43 mL, 54.1 mmol) in dichloromethane (200.0 mL) is added triphenylphosphine dibromide (23.79 g, 54.11 mmol) at 0° C. The reaction is stirred for 1 h then concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography to yield D-1 (8.74 g, 74percent yield), as a white solid. |
11.78 g | Stage #1: With borane-THF In tetrahydrofuran at 25℃; for 16 h; Inert atmosphere Stage #2: With water; sodium carbonate In tetrahydrofuran for 0.25 h; |
Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (4-19) Compound 4-17 (12.50 g, 45.08 mmol) is dissolved in dry THF (125.0 mL) under nitrogen at 25° C. Borane THF complex (99.17 mL, 99.17 mmol) is added via syringe and the mixture is stirred at 25° C. for 16 h. Water (10.0 mL) is slowly added and then 2.0 M Na2CO3 (15.0 mL). This mixture is stirred for 15 min and then is diluted with EtOAc and the organic layers are collected. The organics are rinsed with 1.0 M HCl, dried over MgSO4, and concentrated in vacuo to afford an oil. The oil is purified by silica gel chromatography using a gradient of 10-80percent EtOAc in heptane to yield the desired product, 4-18 (11.78 g), as a white solid. |
2 g | With borane-THF In tetrahydrofuran at 20℃; for 3 h; Sealed tube; Inert atmosphere | Borane-tetrahydrofuran complex in tetrahydrofuran (1.0 M, 15.87 mL, 15.87 mmol) was added dropwise to a stirred solution of 2-(tert-butoxycarbonyl)-1,2,3,4- tetrahydroisoquinoline-6-carboxylic acid (2.0 g, 7.21 mmol) in tetrahydrofuran (50 mL) at ambient temperature under argon in a sealed flask. After stirring for 3 hours, the mixture was carefully quenched with water and sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate (x2) and the combined extracts were washed with brine, dried (anhydrous Na2SO4) and evaporated to give tert-butyl 6- (hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.0 g). LCMS m/z = 207.9 [M+H–isobutylene]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5 g | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h; Stage #2: With water In tetrahydrofuran at 0℃; for 0.25 h; |
Add lithium aluminum hydride (716.49 mg, 18.88 mmol) dropwise to a solutionof 02-tert-butyl 06-methyl 3 ,4-dihydro- 1H-isoquinoline-2,6-dicarboxylate (5.00 g, 17.16mmol) in tetrahydrofuran (85.81 mL) at 0 °C and stir at that temperature for 1 hour. Thenadd water (6 mL) and stir for 15 minutes at 0 °C, filter over CELITE® and wash theCELITE® with ethyl acetate. Concentrate the filtrate under reduced pressure to afford the title compound (4.5 g, 17.09 mmol). MS (m/z): 264 (M+1). |
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