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CAS No. : | 340825-13-0 | MDL No. : | MFCD09751536 |
Formula : | C10H9IO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TUMAMZXVZVEYLU-UHFFFAOYSA-N |
M.W : | 272.08 | Pubchem ID : | 45489800 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.01 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 2.25 |
Log Po/w (XLOGP3) : | 2.67 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.85 |
Log Po/w (SILICOS-IT) : | 3.97 |
Consensus Log Po/w : | 2.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.58 |
Solubility : | 0.0717 mg/ml ; 0.000264 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.68 |
Solubility : | 0.568 mg/ml ; 0.00209 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.34 |
Solubility : | 0.0123 mg/ml ; 0.0000452 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
35.2% | Stage #1: With hydrogenchloride; sodium nitrite In water at 5℃; for 0.5 h; Stage #2: With potassium iodide In water at 60℃; for 3 h; Cooling with ice |
[Synthesis Example 1 - Synthesis 1 of intermediate of specific compound] <Synthesis of Compound (2)> According to the following reaction formula (scheme), Compound (2) was synthesized. 1 2 The amine compound having the above formula 1 was purchased from SIGMA Aldrich Co. and subjected to notreatments before use. A 500 mL beaker was charged with the compound having the above formula 1 (20 g, 119.0 mmol) and 15percent HC1 (96 mL). While the resultant mixture was being maintained at 5°C or lower with ice cooling, aqueous sodium nitrite solution (9.9 g, 143.0 mmol + water (42 mL)) was added dropwise thereto.After completion of dropwise addition, the mixture was stirred at the same temperature for 30 min. Then, aqueous potassium iodide solution (23.7 g, 143.0 mmol + water (77 mL)) was added to the mixture at one time. The beaker was taken out from the ice bath and the mixture was stirred for 2.5 hours. Thereafter, the mixture was heated at 60°C for 0.5 hours until generation of nitrogen was terminated. After cooled to room temperature, the reaction solution was extracted three times with diethyl ether. The organic layer was washed with 5percent aqueous sodium thiosulfate solution (100 mL x 3) and further washed with saturated brine (100 mL x 2). Moreover, the organic layer was dried with sodium sulfate, followed by filtration. The filtrate was concentrated to obtain red oil. The obtained red oil was purified through silica gel chromatography (solvent: ethyl acetate/hexane = 9/1) to obtain a pale orange solid. Further, the obtained solid wasrecrystallized from 2-propanol to obtain Compound (2) as pale orange crystals (yield amount: 11.4 g, yield rate: 35.2percent). The analysis results of Compound (2) are shown below. iH NMR (500 MHz, CDC13, TMS, δ) : 2.13 (quint, 2H, J = 5.7 Hz), 2.64 (t, 2H, J = 6.3 Hz), 2.92 (t, 2H, J = 6.0 Hz), 7.66 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.72 (d, 1H, J = 8.0 Hz) Melting point: 74.0°C-75.0°C Mass spectrometry: GC-MS m/z = 272(M+) From the above analysis results, it was confirmed that a structure of the synthesized product did not contradict that of Compound (2). |
35.2% | Stage #1: With hydrogenchloride; sodium nitrite In water at 5℃; for 0.5 h; Stage #2: With potassium iodide In water at 5 - 60℃; for 3 h; |
The above 6-amino-3,4-dihydro-1(2H)— naphthalenone as a raw material was purchased from SIGMA Aldrich Co. and subjected to no treatments before use. (0169) A 500 mL beaker was charged with 6-amino-3,4-dihydro-1(2H)-naphthalenone (20 g, 119.0 mmol) and 15percent HCl (96 mL). While the resultant mixture was being maintained at 5° C. or lower with ice cooling, aqueous sodium nitrite solution (9.9 g, 143.0 mmol water (42 mL)) was added dropwise thereto. After completion of dropwise addition, the mixture was stirred at the same temperature for 30 min. Then, aqueous potassium iodide solution (23.7 g, 143.0 mmol water (77 mL)) was added to the mixture at one time. The beaker was taken out from the ice bath and the mixture was stirred for 2.5 hours. Thereafter, the mixture was heated at 60° C. for 0.5 hours until generation of nitrogen was terminated. After cooled to room temperature, the reaction solution was extracted three times with diethyl ether. The organic layer was washed with 5percent aqueous sodium thiosulfate solution (100 mL×3) and further washed with saturated brine (100 mL×2). Moreover, the organic layer was dried with sodium sulfate, followed by filtration. The filtrate was concentrated to obtain red oil. (0170) The obtained red oil was purified through silica gel chromatography (solvent: ethyl acetate/hexane=9/1) to obtain a pale orange solid. Further, the obtained solid was recrystallized from 2-propanol to obtain Compound 6 as pale orange crystals (yield amount: 11.4 g, yield rate: 35.2percent). The analysis results of Compound 6 are shown below. (0172) 1H NMR (500 MHz, CDCl3, TMS, δ): 2.13 (quint, 2H, J=5.7 Hz), 2.64 (t, 2H, J=6.3 Hz), 2.92 (t, 2H, J=6.0 Hz), 7.66 (d, 1H, J=8.0 Hz), 7.67 (s, 1H), 7.72 (d, 1H, J=8.0 Hz) (0173) Melting point: 74.0° C.-75.0° C. (0174) Mass spectrometry: GC-MS m/z=272 (M) (actual measured value); 272.082 (theoretical value of molecular weight) (0175) It was confirmed that the synthesized compound is corresponding to compound 6 from the results of the analysis. |
35.2% | Stage #1: With hydrogenchloride; sodium nitrate In water at 5℃; for 0.5 h; Cooling with ice Stage #2: With potassium iodide In water at 60℃; for 3 h; |
In the above formula, the starting material 6-amino-3,4-dihydro-1 (2H) -naphthalenone purchased from SIGMA Aldrich was used as it was.To a 500 mL beaker was added 6-amino-3,4-dihydro-1 (2H)- naphthalenone (20 g, 119.0 mmol) and 15percent HCl (96 mL)While maintaining 5 ° C or less under ice cooling,Aqueous sodium nitrite (9.9g, 143.0mmol + water 42 mL) was slowly added dropwise.After completion of the dropwise addition, the mixture was stirred at the same temperature for 30 minutes,Potassium iodide aqueous solution (23.7 g, 143.0 mmol + water 77 mL) was added at once, the ice bath was removed and the mixture was stirred for 2.5 hours,Thereafter, heating was carried out at 60 ° C. for 0.5 hour until the evolution of nitrogen ceased.After cooling to room temperature, the reaction solution was extracted three times with diethyl ether.The organic layer was washed with 5percent aqueous sodium thiosulfate solution (100 mL × 3 times),And further washed with saturated brine (100 mL × twice).Further, it was dried with sodium sulfate,The filtrate was concentrated to give a red oil.This was purified by silica gel column chromatography (solvent: ethyl acetate / hexane = 9/1) to obtain a pale orange solid.Further, by recrystallization from 2-propanol,Compound 6 was obtained as pale orange crystals (yield 11.4 g, yield 35.2percent). |
17.3 g | Stage #1: With sulfuric acid; acetic acid; sodium nitrite In water at 0℃; Stage #2: With sodium iodide In water at 0 - 20℃; |
Intermediate 8A: 6-Iodo-3,4-dihydronaphthalen-1(2H)-one To a stirred clear solution of 6-amino-3,4-dihydronaphthalen-1(2H)-one (15 g, 93 mmol) in acetic acid (150 mL) and water (150 mL) was added sulfuric acid (5.5 mL, 101 mmol) dropwise at 0° C. A solution of sodium nitrite (12.90 g, 187 mmol) in water (100 mL) was then added dropwise over 40 min at the same temperature. The mixture was stirred at 0° C. for 10 min before being added to a stirred solution of sodium iodide (55.8 g, 372 mmol) in water (600 mL) slowly over 2 h at 0° C. The resulting brown suspension was stirred at 0° C. for 30 min and at room temperature for 1 h. The mixture was extracted with ethyl acetate (400 mL, 2*100 mL). The combined ethyl acetate extracts were washed with water (60 mL), saturated aqueous Na2S2O3 solution until the brown color disappeared, and saturated aqueous K3PO4 (60 mL) solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Flash chromatography purification (330 g silica gel column, gradient elution from 5 to 15percent ethyl acetate in hexanes) afforded 6-iodo-3,4-dihydronaphthalen-1(2H)-one (17.3 g, 63.6 mmol) as a solid. LC/MS M+1=273. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: With acetic acid; sodium nitrite In water at 0℃; for 0.5 h; Stage #2: With potassium iodide In water |
Example 6 (R)-5-Aminomethyl-5,6.J,8-tetrahydro-naphthalene-2-sulfonic acid (3-fluoro-phenyl)- amideThe synthetic procedure described in this Example was carried out according to the process shown in Scheme E.SCHEME EStep 1 6-Iodo-3,4-dihydro-2H-naphthalen-l-oneTo 1.92 g (11.9 mmol) 6-amino-3,4-dihydro-2H-naphthalen-l-one sulfate was added 20 mL water and 20 mL glacial acetic acid. The resulting solution was stirred in an ice bath and a solution of 1.72 grams (25 mmoles) sodium nitrite in 15 mL water was added dropwise over 0.5 hour. The reaction mixture was slowly poured into a well stirred solution of 8 grams (48 mmoles) potassium iodide in 80 mL water. The mixture was extracted with diethyl ether, and the organic phase was washed with water, saturated aqueous sodium hydrogen sulfite, and saturated aqueous sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 <n="60"/>mesh eluting with 5percent ethyl acetate in hexane. 6-Iodo-3,4-dihydro-2H-naphthalen-l-one was obtained as a white solid, 3.12 grams (94percent), m.p. 77-78°. |
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