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CAS No. : | 4456-77-3 | MDL No. : | MFCD00234966 |
Formula : | C9H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QGNQEODJYRGEJX-UHFFFAOYSA-N |
M.W : | 161.16 | Pubchem ID : | 349435 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.41 |
TPSA : | 46.17 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) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 1.26 |
Log Po/w (XLOGP3) : | 0.65 |
Log Po/w (WLOGP) : | 0.12 |
Log Po/w (MLOGP) : | 0.89 |
Log Po/w (SILICOS-IT) : | 1.78 |
Consensus Log Po/w : | 0.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.62 |
Solubility : | 3.88 mg/ml ; 0.0241 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.2 |
Solubility : | 10.3 mg/ml ; 0.0638 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.04 |
Solubility : | 0.145 mg/ml ; 0.000902 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.49 |
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 |
---|---|---|
14% | for 16 h; Reflux | PBr3 (10 mL) was added slowly to 33 (1.41 g, 8.7 mmol)and the mixture was heated at reflux for 16 h. The evaporation residue wasquenched (sat. aq. NaHCO3) and extracted thrice with CHCl3.Chromatography (EtOAc / petroleum ether 3:17), followed by chromatography(EtOAc / petroleum ether 1:49) gave 34 (358 mg, 14percent) aswhite crystals: mp 148-150°C (lit.4mp 147-147.5°C); 1H NMR ((CD3)2SO) d 7.93 (1 H, td, J = 6.9, 1.3 Hz, 6-H), 8.00 (1 H, td, J = 6.9, 1.2 Hz, 7-H), 8.10 (1 H, dt, J = 8.1, 0.6 Hz, 5-H), 8.27 (1 H, d, J = 8.4 Hz, 8-H), 8.38 (1 H, s, 4-H); 13C NMR((CD3)2SO) (HSQC / HMBC) d 124.66 (4-C), 126.85(5-C), 127.13 (8a-C), 127.68 (4a-C), 127.89 (8-C), 130.69 (6-C), 132.69 (7-C),138.74 (3-C), 143.18 (1-C). Further elution gave 35 (66 mg, 4percent) as whitecrystals: mp 61-63°C (lit.4mp 63-64°C; 1H NMR ((CD3)2SO)(NOE) d 7.80 (1 H, td, J= 8.0, 1.2 Hz, 6-H), 7.90 (1 H, dt, J= 8.3, 1.2 Hz, 7-H), 8.03 (1 H, d, J= 8.3 Hz, 5-H), 8.23 (1 H, d, J = 8.3Hz, 8-H), 8.27 (1 H, s, 4-H), 9.24 (1 H, s, 1-H); 13C NMR((CD3)2SO) (HSQC / HMBC) d 123.53 (4-C), 125.76(5-C), 127.25 (4a-C), 127.80 (8-C), 128.13 (6-C), 131.68 (7-C), 135.19 (3-C),137.46 (8a-C), 153.19 (1-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With P,P-dichlorophenylphosphine oxide In tetrahydrofuran; water at 20 - 160℃; | EXAMPLE 60B 1,3-dichloroisoquinoline The product from Example 60A (6.5 g, 40.4 mmol) was treated with phenylphosphonic dichloride (11.5 mL, 81.1 mmol) and heated at 160° C. for 3 hours. The reaction was allowed to cool to room temperature and stand overnight. The resulting waxy orange material was dissolved in tetrahydrofuran (200 mL), treated with water (60 mL), and then concentrated under reduced to remove the tetrahydrofuran. The remaining aqueous material was neutralized with concentrated NH4OH and extracted with ethyl acetate. The ethyl acetate phases were combined, washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure to provide the title compound as yellow flakes (6.92 g, 74percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: at 180℃; for 2 h; Stage #2: With potassium hydroxide In waterCooling with ice |
b) 1,3-Dibromoisoquinoline; A mixture of isoquinoline-1 ,3(2H,4/-/)-dione (preparation 20a, 0.65 g, 4.02 mmol), phosphorous tribromide (1.51 mL, 16.05 mmol) and phosphoric tribromide (1.04 g, 3.61 mmol) was stirred at 180 °C. After 2 hours, the mixture was cooled, poured onto ice- water and 2N aqueous potassium hydroxide was added until the pH was 8-9. The aqueous layer was extracted with toluene, and the organic layer was filtered through neutral alumina and the filtrate was evaporated to give the title compound (0.58 g, 56percent) as a white solid.LRMS (m/z): 286/288/290 (M+1)+.1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.67 - 7.76 (m, 3 H) 7.84 (s, 1 H) 8.24 (d, J=8.40 Hz, 1 H) |
56% | at 180℃; for 2 h; | A mixture of isoquinoline-1,3(2H,4H)-dione (preparation 20a, 0.65 g, 4.02 mmol), phosphorous tribromide (1.51 mL, 16.05 mmol) and phosphoric tribromide (1.04 g, 3.61 mmol) was stirred at 180 title compound (0.58 g, 56percent) as a white solid.LRMS (m/z): 286/288/290 (M+1)+.1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.67 - 7.76 (m, 3 H) 7.84 (s, 1 H) 8.24 (d, J=8.40 Hz, 1 H) |
35% | With phosphorus(V) oxybromide In 1,4-dioxane for 22 h; Reflux | Isoquinoline-1,3-dione 33 (3.00 g, 18.6 mmol) was heated under reflux withPOBr3 (10.7 g, 37 mmol) in 1,4-dioxane (20 mL) for 22 h.The mixture was quenched with MeOH, then water. The mixture, in water, wasextracted thrice with CH2Cl2. Drying, evaporation andrecrystallisation (PhMe) gave 34 (1.87 g, 35percent) as an off-white solid, withproperties as above |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | for 16 h; Reflux | PBr3 (10 mL) was added slowly to 33 (1.41 g, 8.7 mmol)and the mixture was heated at reflux for 16 h. The evaporation residue wasquenched (sat. aq. NaHCO3) and extracted thrice with CHCl3.Chromatography (EtOAc / petroleum ether 3:17), followed by chromatography(EtOAc / petroleum ether 1:49) gave 34 (358 mg, 14percent) aswhite crystals: mp 148-150°C (lit.4mp 147-147.5°C); 1H NMR ((CD3)2SO) d 7.93 (1 H, td, J = 6.9, 1.3 Hz, 6-H), 8.00 (1 H, td, J = 6.9, 1.2 Hz, 7-H), 8.10 (1 H, dt, J = 8.1, 0.6 Hz, 5-H), 8.27 (1 H, d, J = 8.4 Hz, 8-H), 8.38 (1 H, s, 4-H); 13C NMR((CD3)2SO) (HSQC / HMBC) d 124.66 (4-C), 126.85(5-C), 127.13 (8a-C), 127.68 (4a-C), 127.89 (8-C), 130.69 (6-C), 132.69 (7-C),138.74 (3-C), 143.18 (1-C). Further elution gave 35 (66 mg, 4percent) as whitecrystals: mp 61-63°C (lit.4mp 63-64°C; 1H NMR ((CD3)2SO)(NOE) d 7.80 (1 H, td, J= 8.0, 1.2 Hz, 6-H), 7.90 (1 H, dt, J= 8.3, 1.2 Hz, 7-H), 8.03 (1 H, d, J= 8.3 Hz, 5-H), 8.23 (1 H, d, J = 8.3Hz, 8-H), 8.27 (1 H, s, 4-H), 9.24 (1 H, s, 1-H); 13C NMR((CD3)2SO) (HSQC / HMBC) d 123.53 (4-C), 125.76(5-C), 127.25 (4a-C), 127.80 (8-C), 128.13 (6-C), 131.68 (7-C), 135.19 (3-C),137.46 (8a-C), 153.19 (1-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With urea In neat (no solvent) at 175 - 185℃; for 2 h; | 2-Carboxyphenylaceticacid 32 (20.0 g, 111 mmol) washeated with finely ground urea (7.33 g, 122 mmol) at 175-185°C for 2 h. Cooling and recrystallisation(MeOH) gave 33 (12.0 g, 67percentpercent) as anoff-white solid: mp 220-222°C (lit.3mp 236-238°C); 1HNMR ((CD3)2SO) d 4.09 (3 H, s, CH2), 7.44 (1 H,d, J = 7.6 Hz, 5-H), 7.51 (1 H, t, J = 7.6 Hz, 7-H), 7.70 (1 H, td, J = 7.6, 1.2 Hz, 6-H), 8.07 (1 H, dd, J = 7.8, 1.1 Hz, 8-H), 11.36 (1 H, s,N-H); 13C NMR ((CD3)2SO) (HSQC /HMBC) d 35.92 (4-C), 124.95 (8a-C), 127.16 (7-C), 127.41 (8-C), 127.87 (5-C),133.47 (6-C), 136.66 (4a-C), 165.34 (1-C), 170.99 (3-C). |
47% | With urea In 1,2-dimethoxyethane at 175℃; Sealed tube | A solution of 2-(carboxymethyl)benzoic acid (1.00 g, 5.55 mmol) and urea (0.37 g, 6.10 mmol) in ethylene glycol anhydrous (20 mL) was heated in a sealed tube at 175 solid.LRMS (m/z): 162 (M+1)+. |
34% | With urea In methanol | Step 1 A mixture of homophthalic acid (200 g, 1.09 mol) and urea (80 g, 1.31 mol) was ground to a fine powder then heated at 175-185° C. until it had melted then resolidified. The mixture was cooled to ambient temperature, methanol (500 ml) was added, then the mixture was heated under reflux for 20 minutes, filtered, and allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with methanol and dried in vacuo to give homophthalimide (60 g, 34percent) as a solid; m.pt. 235-240° C.; δH 4.0 (2H, s), 7.3-7.75 (3H, m), 8.10 (1H, d), 11.20 (1H, br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: With ammonia In water Stage #2: at 200℃; |
EXAMPLE 60A isoquinoline-1,3(2H,4H)-dione 2-(Carboxymethyl)benzoic acid (10 g, 55.6 mmol) was dissolved in concentrated NH4OH (15 mL) and then was evaporated to dryness under reduced pressure. The process was repeated with additional NH4OH (5 mL). The resulting residue was treated with 1,2-dichlorobenzene (20 mL) and heated with stirring at 200° C. without a condenser allowing the solvent to evaporate. The concentrated mixture was allowed to cool to room temperature, diluted with methanol (20 mL), and allowed to stand overnight. The precipitate was collected by filtration, washed with methanol, and dried under reduced pressure to provide the title compound as tan needles (6.6 g, 74percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | at 175℃; sealed tube | PREPARATION 20; a) lsoquinoline-1,3(2H,4H)-dione; A solution of 2-(carboxymethyl)benzoic acid (1.00 g, 5.55 mmol) and urea (0.37 g, 6.10 mmol) in ethylene glycol anhydrous (20 mL) was heated in a sealed tube at 175 °C with stirring. After stirring overnight the mixture was cooled, poured onto water and 1 N aqueous hydrochloric acid was added until the pH was 4-5. The aqueous layer was extracted with ethyl acetate, dried (Na2S04) and evaporated. Methanol and few drops of hexanes were added to the crude and the precipitate was filtered, washed whith hexanes and dried to give the desired compound (0.43 g, 47percent) as a solid. LRMS (m/z): 162 (M+1)+. |
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