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CAS No. : | 2892-62-8 | MDL No. : | MFCD00037150 |
Formula : | C12H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XBRWELTXMQSEIN-UHFFFAOYSA-N |
M.W : | 226.27 | Pubchem ID : | 65108 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.78 |
TPSA : | 52.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 2.97 |
Log Po/w (XLOGP3) : | 2.43 |
Log Po/w (WLOGP) : | 1.98 |
Log Po/w (MLOGP) : | 0.01 |
Log Po/w (SILICOS-IT) : | 2.95 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.25 |
Solubility : | 1.28 mg/ml ; 0.00568 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.18 |
Solubility : | 0.15 mg/ml ; 0.000665 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.43 |
Solubility : | 0.0843 mg/ml ; 0.000372 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H317-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 |
---|---|---|
74% | for 3 h; Reflux | A solution of squaric acid (1) (2.00 g, 17.54 mmol) in n-BuOH (50 mL) was refluxed under stirring for 3 h. After cooling on an ice bath, 50 mL of diethyl ether (Et2O) was added to the mixture, which was sequentially washed with cold distilled water, cold saturated aqueous NaHCO3, and cold distilled water. The organic layer, after separation, was dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The resulting brownish oil (2.92 g, 74percent yield) was chromatographically pure and used in the next reaction without further purification. Yield: 74percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | for 3h;Reflux; | A solution of squaric acid (1) (2.00 g, 17.54 mmol) in n-BuOH (50 mL) was refluxed under stirring for 3 h. After cooling on an ice bath, 50 mL of diethyl ether (Et2O) was added to the mixture, which was sequentially washed with cold distilled water, cold saturated aqueous NaHCO3, and cold distilled water. The organic layer, after separation, was dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The resulting brownish oil (2.92 g, 74% yield) was chromatographically pure and used in the next reaction without further purification. Yield: 74%. |
In water; toluene; | A. 1,2-Dibutoxy-1-cyclobutene-3,4-dione Protected by a nitrogen atmosphere, a mixture of 1-butanol (64 mL), toluene (42 mL), and 1,2-dihydroxy-1-cyclobutene-3,4-dione (21.43 g, 0.1878 mole) was heated under reflux with stirring under a Dean-Stark water separator until water stopped passing(7.6 mL of water was collected). Reflux was continued for a further 30 minutes, then the excess toluene and butanol were distilled off under reduced pressure (50-100 mm Hg) to give the title compound as a yellow liquid. The concentrate was diluted with 25 mL of methanol. | |
In toluene; | A. 1,2-Dibutoxy-1-cyclobutene -3,4-dione A mixture of 1-butanol (48 mL), toluene (32 mL), and 1,2-dihydroxy-l-cyclobutene-3,4-dione (16.0 g, 0.1402 mole) was heated at reflux under a nitrogen atmosphere with stirring under a Dean-Stark water separator until water stopped passing over. The resulting solution of the title compound was cooled to 0-5 C. |
In toluene; | A. 1,2-Dibutoxy-1-cyclobutene-3,4-dione A mixture of 1-butanol (3 L), toluene (2 L) and 1,2-dihydroxy-1-cyclobutene-3,4-dione (1 kg; 8.767 moles) was refluxed with stirring under a Dean-Stark separator until water stopped passing(theory:0.316 L). The excess toluene and butanol were then removed by distillation under reduced pressure to give the title compound as a yellow liquid. The concentrate was diluted with methanol (1.5L) and used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With triethylamine; In butan-1-ol; at 70℃; for 1h;Inert atmosphere; | General procedure: The corresponding indolium iodide (1 equiv.) and 3, 4-dibutoxycyclobut-3-ene-l,2-dione (1 equiv) were dissolved in 1-butanol in a 50 mL two necked round bottomed flask and triethylamine (1.2 equiv) was added into the reaction mixture. The reaction mixture was heated at 70 C for 1 h under nitrogen atmosphere. The reaction mixture cooled to room temperature, and the solvents were removed under reduced pressure. The reaction mixture was purified by column chromatography (Si02, 100-200 mesh) 5% EtOAc and 95% petroleum ether to afford the required compound as a yellow solid. (0114) (E)-2-((2-butoxy-3,4-dioxocyclobut-l-en-l-yl)methylene)-l,3,3-trimethyl-indoline (8): 1.6g, Yield: 74 %; 1H NMR (CDC13, 200MHz) delta: 7.29-724 (m, 2H), 7.07 (t, /=7.4Hz, IH), 6.88 (d, /=7.24Hz, IH), 5.36 (s, IH), 4.85 (t, /=6.6Hz, 2H), 3.37 (s, 3H), 1.95-1.79 (m, 2H), 1.61 (s, 6H), 1.58- 1.42(m, 2H), 1.01(t, /=7.2Hz, 3H); 13C NMR (CDCI3, 50 MHz) delta: 192.7, 187.5, 173.5, 168.3, 142.6, 140.9, 127.7, 122.6, 121.9, 108.4, 81.2, 73.7, 47.9, 43.0, 32.1, 31.4, 26.9, 26.6, 26.2, 22.4, 18.7, 13.9, 13.7; HRMS (m/z): [M + H]+ calcd for C20H24NO3: 326.1751 ;found: 327.1570; [M + Na]+ calcd for C20H23NO3Na: 348.1570; found: 348.1569. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; In butan-1-ol; at 20 - 75℃; for 40h; | Synthesis of Compound No. 50 (Intermediate-c) In a reactor flask purged with nitrogen gas, 1.4 g (2.0 mmol) of the compound No. 40 obtained in Example 2, 0.50 g (2.2 mmol) of 3,4-dibutoxy-3-cyclobutene, 4.0 g of butanol, and 0.24 g of pyridine were charged, and the resulting mixture was stirred at room temperature for 15 hours, at 50C for 4 hours, and at 75C for 21 hours. The reaction solution was cooled to room temperature and concentrated to dryness under reduced pressure. The resulting residue was purified with a column (silica gel, chloroform : acetone = 10 : 1) to obtain 0.92 g of a brown amorphous product (yield: 70%). The brown amorphous product was subjected to the 1H-NMR analysis. The brown amorphous product was identified as the aimed product of compound No. 50. The result of the 1H-NMR analysis is shown below. Result of 1H-NMR Analysis (solvent: CDCl3) (0.59; m; 1), (0.77; m; 1), (0.99; m; 3), (1.39; m; 3), (1.62; s; 3), (3.84; m; 4), (3.98; s; 5), (4.69; t; 2), (4.85; t; 2), (5.61; s; 1), (6.82; dd; 2), (6.96; t; 2), (7.10; t;1), and (7.23; m; 4) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With pyridine; In butan-1-ol; at 135℃; for 3h; | Synthesis of Compound No.1 (Cyanine compound represented by the general formula (I)) In a reactor flask purged with nitrogen gas, 0.70 g (1 mmol) of the compound No. 40 obtained in Example 2, 57 mg (0.50 mmol) of 3,4-dihydroxy-3-cyclobutene, 2.7 g of butanol, and 0.12 g of pyridine were charged, and the resulting mixture was heated at 135C for 3 hours. The reaction solution was cooled to room temperature and concentrated to dryness under reduced pressure. Then, the resulting residue was purified with a column (silica gel, chloroform : acetone = 10 : 1) and recrystallized with ethanol to obtain 0.23 g (yield: 42%) of brown crystals. The resulting brown crystals were identified as the aimed product of compound No. 1. The results of analysis about the brown crystals are shown below.Results of Analysis (1) 1H-NMR (solvent: CDCl3) (Peak-top chemical shift in ppm; multiplicity; number of protons) (0.54; m; 2), (0.77; m; 2), (1.21; m; 4), (1.65; s; 6), (1.80-1.91; m; 8), (3.82; t; 8), (3.97; s; 10), (4.34; m; 8), (6.09; t; 2), (6.75; d; 4), (6.92; t; 2), and (7.15-7.36; m; 11)(2) IR absorption (cm-1) 2925, 1600, 1491, 1461, 1281, 1241, 1182, 1136, and 1075(3) UV absorption (solvent: chloroform) lambdamax; 642 nm, E; 2.82×105 (4) Decomposition temperature (TG-DTA: in 100 ml/min of N2 gas stream, at 10C/min of temperature elevation rate) 287C; peak-top |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethanol; at 40 - 60℃; for 4h; | [0107] 1 g (2.4 mmol) of 1,2,3,3-tetramethylindoleninium-5-sulfonate (1c) was dissolved in 10 mL of ethanol containing 50 muL of triethylamine. The temperature of the reaction mixture was increased to 40 C., and 640 mul (2.9 mmol) of squaric acid dibutyl ester (2c) were slowly added. The reaction mixture was then heated to 60 C. and stirred for 4 h. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the yellow crystalline residue was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[0100] 22 mul (0.1 mmol) of squaric acid dibutyl ester were added to 47 mg (0.1 mmol) of 1-(epsilon-carboxypentyl)-2,3,3-trimethylindolenium-5-sulfonic acid potassium salt (1a). The resulting mixture was refluxed in 8 mL of ethanol with 140 muL of triethylamine for 30 min. 220 mul of 1 M aqueous NaOH were then added, and the mixture was refluxed for 30 min. After the mixture was cooled to room temperature, 2.3 mL of 1 M hydrochloric acid were added, and the solvent was removed under reduced pressure to obtain the monosubstituted squaraine derivative (5a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine; In tetrahydrofuran; at 20℃; for 15h; | [0150] 2.16 mL (10 mmol) of squaric acid dibutylester (2c) were dissolved in 40 mL of THF. 660 mg (10 mmol) of malonedinitrile were added under stirring. A solution of 1.64 mL of triethylamine in 3 mL of THF was then added, and the mixture was stirred at room temperature for 15 h. The solvent was removed under reduced pressure, and a yellow-brown oil remained. The raw product is purified by MPLC using silica gel as the stationary phase and methanol as eluent. [0151] Yield: 173 mg (63%) of (2d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.105 g (86%) | In tetrahydrofuran; | EXAMPLE 1 3-(1,1-Dimethylpropylamino)-4-[(pyridin-4-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione A solution of 3,4-dibutoxycyclobut-3-ene-1,2-dione (4.526 g, 20 mmol) and 1,1-dimethylpropylamine (1.743 g, 20 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature for 19.5 hours. The solvent was removed and the residue was chromatographed (gravity, chloroform-hexane) on neutral, activity III silica (150 g). The white solid isolated from the appropriate eluates was recrystallized from hexane to give 4.105 g (86%) of a white product: mp 56.5-57.5 C. (softens 55.5 C.), One gram of this material was recrystallized twice from hexane to provide 0.794 g of 3-butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione as a white solid: mp 56-57 C. (softens 55 C.); 1 H NMR (DMSO-d6): delta 8.63 and 8.48 (two br s 1H, rotomers), 4.67 (m, br, 2H), 1.67 (m, br, 4H), 1.39 (m, 2H), 1.26 (m, br, 6H), 0.91 (t, 3H), 0.78 (t, 3H). IR (KBr): 3170, 1790, 1700 cm-1; MS (m/z) 239 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 2c:; Dibutyl squarate was reacted with 3-ethyl-2-methyl- benzothiazolium iodide (1 : 1 ratio) in ethanol at reflux. After 30 minutes refluxing, the reaction mixture was filtered while hot. An orange colored solid crystallized out of the filtrate while cooling, which was separated and re-suspended in ethanol and treated with 40% NaOH solution under reflux. After 30 minutes, the contents were cooled and acidified with 2 N HCl (pH adjusted to 4). The product was extracted with chloroform to give intermediate 2c. 1H NMR (CDCl3, TMS) delta ppm: 1.385 (t, CH3, 3H); 1.456 (t, CH3, 3H); 4.064 (q, CH2, 2H); 4.794 (q, CH2, 2H); 5.479 (s, CH, IH); 7.026-7.518 (m, aromatic, 4H). MoI. Wt calculated for C14H11NO3S is 273(M+), found 273 (FAB) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; methanol; acetone; | EXAMPLE 1 1-Amino-2-butoxy-1-cyclobutene-3,4-dione Preparation A A solution of 1,2-dibutoxy-1-cyclobutene-3,4-dione (6.09, 0.027 mole) in 40 mL of tetrahydrofuran was cooled to 5 C. in an ice-water bath and treated dropwise over a period of 9 minutes with a solution of 1.8 mL of concentrated ammonium hydroxide in a mixture of 8 mL of tetrahydrofuran and 1 mL of methanol. After stirring at 5 C. for 30 minutes and at ambient temperature for 90 minutes the mixture was concentrated under reduced pressure to a slurry. A small amount of Skellysolve B was added and the product was collected by filtration after 16 hours of standing at 0 C. to give 3.26 g of the title compound. A sample (8.54 g) was partly dissolved in acetone, filtered and cooled to give 4.51 g of purified title compound; mp=165.5-168 C. (clear melt). Anal. Calcd. for C8 H11 NO3: C, 56.79; H, 6.56; N, 8.28. Found: C, 56.46; H, 6.19; N, 8.56. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.8% | With sodium hydroxide; In methanol; water; | B. 1-Butoxy-2-(3-bromopropylamino)-1-cyclobutene-3,4-dione Solid 3-bromopropylamine hydrobromide (41.52 g, 0.1897 mole) was added with stirring to a solution of sodium hydroxide (7.73 g, contains 0.187 mole) in methanol (150 mL) at 22 C., stirred for 15 minutes, then cooled to 0 C. to give a hazy solution of bromopropylamine base. The solution of bromopropylamine base was added slowly (over 20 minutes) with vigorous stirring to the product of Step A in methanol at 0 C. The mixture was stirred at 22 C. for 1.5 hours, polish filtered through diatomaceous earth (washed through with 50 mL of methanol) and added with vigorous stirring to water (1060 mL). The stirred mixture was cooled to -10 C. over several hours. The solid was collected by filtration, washed well with water (0 C., 440 mL) and dried in vacuo to give 50.0 g (91.8% yield) of the title compound as an off-white solid; m.p.=66-68 C. |
84% | With sodium hydroxide; In methanol; water; | B. 1-Butoxy-2-(3-brompropylamino)-1-cyclobutene-3,4-dione In another flask, 3-bromopropylamine hydrobromide (1.977 kg; 8.849 moles) was added with stirring to a cooled solution of sodium hydroxide (0.35 kg; 8.745 moles) in methanol (5.5L) and stirred for 30 minutes to give a hazy solution of bromopropylamine base. The solution of bromopropylamine base, cooled to 0 C., was slowly added dropwise with vigorous stirring and cooling to maintain the temperature below to the methanolic solution of Step A containing 1,2-dibutoxy-1-cyclobutene-3,4-dione. The mixture was stirred at 20 C. for 2 hours, polish filtered through diatomaceous earth, washed with methanol (2*0.25L) and the filtrate was added over a period of 1 hour with vigorous stirring to water (31.1L). The mixture was stirred at 0 C. for 2 hours. The solid was collected by filtration, washed with water (3*2L) and dried to vacuo at 50 C. to give 2137 g (84% yield) of the title compound as an off-white solid; m.p.=69 C. |
With sodium hydroxide; In methanol; toluene; | B. 1-Butoxy-2-(3-bromopropylamino)-1-cyclobutene-3,4-dione Solid 3-bromopropylamine hydrobromide (31.0 g, 0.1416 mole) was added with stirring to a solution of sodium hydroxide (5.77 g, 0.140 mole) in methanol (152 mL) and stirred at ambient temperature for 15 minutes. The solution was cooled to 0-5 C. and then added with stirring to the solution of Step A. The mixture was stirred at 22 C. for 1.5 hours then concentrated under reduced pressure (40 C.) to about 120 mL volume. Toluene (120 mL) was added and the mixture was washed with water (240 mL). The organic layer was dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give 38.64 g (95.0 % yield) of the title compound as an off-white solid. The product was used without further purification in the subsequent reaction. A sample was recrystallized from methanol at -60 C. to give pure title compound; m.p.=56-57 C. (crystal form changes), 68 C. (melting complete). Anal. Calcd. for C11 H16 BrNO3: C, 45.53; H, 5.56; N, 4.83; Br, 27.54. Found: C, 45.59; H, 5.55; N, 4.81; Br, 27.41. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.8% | With sodium hydroxide; In methanol; water; | B. 1-Butoxy-2-(3-bromopropylamino)-1-cyclobutene-3,4-dione Solid 3-bromopropylamine hydrobromide (41.52 g, 0.1897 mole) was added with stirring to a solution of sodium hydroxide (7.73 g, contains 0.187 mole) in methanol (150 mL) at 22 C., stirred for 15 minutes, then cooled to 0 C. to give a hazy solution of bromopropylamine base. The solution of bromopropylamine base was added slowly (over 20 minutes) with vigorous stirring to the product of Step A in methanol at 0 C. The mixture was stirred at 22 C. for 1.5 hours, polish filtered through diatomaceous earth (washed through with 50 mL of methanol) and added with vigorous stirring to water (1060 mL). The stirred mixture was cooled to -10 C. over several hours. The solid was collected by filtration, washed well with water (0 C., 440 mL) and dried in vacuo to give 50.0 g (91.8% yield) of the title compound as an off-white solid; m.p.=66-68 C. |
84% | With sodium hydroxide; In methanol; water; | B. 1-Butoxy-2-(3-brompropylamino)-1-cyclobutene-3,4-dione In another flask, 3-bromopropylamine hydrobromide (1.977 kg; 8.849 moles) was added with stirring to a cooled solution of sodium hydroxide (0.35 kg; 8.745 moles) in methanol (5.5L) and stirred for 30 minutes to give a hazy solution of bromopropylamine base. The solution of bromopropylamine base, cooled to 0 C., was slowly added dropwise with vigorous stirring and cooling to maintain the temperature below to the methanolic solution of Step A containing 1,2-dibutoxy-1-cyclobutene-3,4-dione. The mixture was stirred at 20 C. for 2 hours, polish filtered through diatomaceous earth, washed with methanol (2*0.25L) and the filtrate was added over a period of 1 hour with vigorous stirring to water (31.1L). The mixture was stirred at 0 C. for 2 hours. The solid was collected by filtration, washed with water (3*2L) and dried to vacuo at 50 C. to give 2137 g (84% yield) of the title compound as an off-white solid; m.p.=69 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In ethanol; | Example 72 3-[4-(3,4-Dioxo-2-pyrrolidin-1-yl-cyclobutyl-1-enyl)-piperazin-1-ylmethyl]-2-phenyl-quinoline-4-carboxylic acid ((S)-1-cyclohexyl-ethyl)-amide 0.25 g (0.55 mmol) of 2-phenyl-3-piperazin-1-ylmethyl-quinoline-4-carboxylic acid ((S)-1-cyclohexyl-ethyl)-amide (compound of Example 34) and 0.124 g (0.55 mmol) of 3,4-di-N-butoxy-3-cyclobuten-1,2-dione (Aldrich) were stirred in 3 ml of ethanol at room temperature for 7 h. Then, 0.15 g (2.2 mmol) of pyrrolidine was added and stirring was continued for one night. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on silicagel (CH2Cl2/MeOH: 98/2). After concentration of the desired fractions, the residue was crystallized from di-isopropyl ether. The solid obtained was purified again by chromatography on silicagel (EtOAc as eluent). After concentration of the desired fractions the residue was re-crystallized from di-isopropyl ether to afford 0.180 g (yield 54%) of the title compound as white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In tetrahydrofuran; water; | (144-1) To a solution of 0.073 g of 3,4-di-n-butoxy-3-cyclobuten-1,2-dione (0.323 mmol) in 2 mL of THF was added 0.1 g of the compound from Example 1, the process (1-4) (0.293 mmol), and the solution was stirred for 4 hours. After adding 0.033 mL of 3-aminomethylpyridine (0.327 mmol), the solution was reacted for a day. After completion of the reaction, water was added to the solution, and the mixture was extracted twice with methyl ethyl ketone. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was triturated with methanol to give 0.12 g of N-[2-(N-tert-butoxycarbonylamino)phenyl]-4-[N-[3-[(pyridin-3-yl)methylamino]cyclobuten-1,2-dion-4-yl]aminomethyl]benzamide (Yield: 78%) 1H NMR(270 MHz, DMSO-d6) delta ppm: 1.44(9H, s), 4.75-4.81(4H, m), 7.15(1H, dt, J=2.2, 7.4 Hz), 7.20(1H, dt, J=2.2, 7.4 Hz), 7.40(1H, dd, J=2.2, 7.4 Hz), 7.47(2H, d, J=8.1 Hz), 7.54(2H, dd, J=2.2, 7.4 Hz), 7.73(1H, m), 7.94(2H, d, J=8.1 Hz), 8.50(1H, m), 8.55(1H, d, J=1.5 Hz), 8.67(1H, s), 9.82(1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In tetrahydrofuran; at 20℃; for 20h; | A solution of di-n-butylsquarate (0.15 mL, 0.69 mmol) and the hydrochloride salt compound prepared as in Example 3 above (116 mg, 0.65 mmol) in dry THF was treated with 1 equivalent of sodium methoxide. After stirring the reaction mixture at room temperature for 20 hours, the title compoundcompound was collected by filtration as a precipitate and used in the next reaction step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In tetrahydrofuran; at -78℃; | [0064] To a solution of 3,4-dibutoxy-cyclobut-3-ene-1,2-dione (1 equiv.) in THF at -78 C. was added allyl or vinyl magnesium bromide (1 M, 1.35 equiv.) dropwise. The reaction mixture was stirred for 6-8 h and the reaction monitored by TLC for disappearance of starting material. The reaction was quenched with water and extracted with CH2Cl2 (3×100 mL). The organic layers were collected, washed with brine (25 mL), dried over Na2SO4 and concentrated in vacuo. Flash column chromatography (SiO2, 15-20% EtOAc in Hexanes) yielded compounds 53 or 54. [0065] 53: Yield (73%), yellow oil, Rf=0.30 (20% EtOAc in Hexanes); 1H NMR (CDCl3, 300 MHz) delta 5.72-5.60 (1H, m), 5.09-5.0 (2H, m), 4.39-4.24 (2H, m), 4.17-4.11 (3H, m), 2.61-2.46 (2H, m), 1.72-1.62 (2H, m), 1.58-1.49 (2H, m), 1.43-1.18 (4H, m), 0.91-0.73 (6H, m); 13C NMR (CDCl3, 300 MHz) delta 187.5, 168.2, 133.0, 132.6, 199.2, 85.9, 73.4, 70.9, 37.9, 32.1, 31.8, 19.1, 18.9, 14.0, 13.9; HRMS calcd for C15H24O4 [M]Na+291.1567. found 291.1564 [0066] 54: Yield (59%), red oil, Rf=0.30 (20% EtOAc in Hexanes); 1H NMR (CDCl3, 300 MHz) delta 6.58-5.32 (3H, m), 4.75-4.71 (1H, t), 4.39-4.35 (1H, t), 3.70-3.57 (2H, m), 1.82-1.19 (9H, m), 0.94-0.82 (6H, m); 13C NMR (CDCl3, 300 MHz) delta 194.9, 193.4, 190.7, 180.9, 173.7, 128.9, 127.4, 122.7, 122.22, 122.2, 113.3, 77.9, 77.5, 77.1, 75.3, 73.8, 66.0, 62.9, 32.2, 32.1, 31.63, 19.5, 19.2, 19.1, 18.8, 14.2, 13.94, 13.9; HRMS Calcd. for C14H22O4 [M]Na+277.1413. found 277.1410 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With triethylamine; In butan-1-ol; at 70℃; for 1h; | In a round bottom flask fitted with condenser, 1.26 g (4 mmol) of compound 2, 900 mg (4 mmol) of <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> and 0.8 mL of triethylamine were dissolved in 6 mL butanol. Reaction mixture was heated at 70 C for 1 h leading to green solution. Solvent was removed at rotary evaporator and product was purified by column chromatography (Silica gel) with ethyl acetate and hexane as eluent giving 920 mg of titled compound in 50% yield and 99% purity as confirmed by HPLC. Compound was confirmed by MALDI-TOF-mass, observed [M + H]+ 340.60 for C21H25NO3 (calcd 339.18). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triethylamine; In methanol; at 20℃;Inert atmosphere; | General procedure: To a solution of the suitable Boc azapeptide vinylsulfone 1 (1 equiv) in DCM was added TFA (4 equiv). After 2 h the solvent was removed under reduced pressure affording quantitatively slightly yellow oil. The residue was dissolved in methanol and NEt3 (2 equiv) was added followed by the addition of the suitable squaric acid derivative (1 equiv) under N2. The reaction mixture was stirred overnight at rt. The solvent was then removed under reduced pressure and the obtained residue was purified by column chromatography (Hexane/AcOEt 3:2) affording the corresponding product as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine; In methanol; at 20℃;Inert atmosphere; | General procedure: To a solution of the suitable Boc azapeptide vinylsulfone 1 (1 equiv) in DCM was added TFA (4 equiv). After 2 h the solvent was removed under reduced pressure affording quantitatively slightly yellow oil. The residue was dissolved in methanol and NEt3 (2 equiv) was added followed by the addition of the suitable squaric acid derivative (1 equiv) under N2. The reaction mixture was stirred overnight at rt. The solvent was then removed under reduced pressure and the obtained residue was purified by column chromatography (Hexane/AcOEt 3:2) affording the corresponding product as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine; In methanol; at 20℃;Inert atmosphere; | General procedure: To a solution of the suitable Boc azapeptide vinylsulfone 1 (1 equiv) in DCM was added TFA (4 equiv). After 2 h the solvent was removed under reduced pressure affording quantitatively slightly yellow oil. The residue was dissolved in methanol and NEt3 (2 equiv) was added followed by the addition of the suitable squaric acid derivative (1 equiv) under N2. The reaction mixture was stirred overnight at rt. The solvent was then removed under reduced pressure and the obtained residue was purified by column chromatography (Hexane/AcOEt 3:2) affording the corresponding product as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With triethylamine; In butan-1-ol; at 75℃; for 1h; | General procedure: An alcohol solution (11, 13, 15: BuOH; 12, 14: EtOH, 12 mL) of a 2,3,3-trimethyl-3H-indolium iodide 5-7 (8 mmol), a 3,4-dialkoxycyclobut-3-ene-1,2-dione 8-10 (8 mmol), and triethylamine (1.6 mL) was heated at 75 C (11: 0.3 h; 12, 14: 2 h; 13, 15: 1 h). After the reaction was completed, to the mixture were added water (20 mL) and dichloromethane (50 mL). The dichloromethane layer was separated, washed with water (50 mL×3), and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The product was purified by silica gel column chromatography (CH2Cl2 then CH2Cl2/AcOEt=20:1) and recrystallized from hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With triethylamine; In butan-1-ol; at 75℃; for 1h; | General procedure: An alcohol solution (11, 13, 15: BuOH; 12, 14: EtOH, 12 mL) of a 2,3,3-trimethyl-3H-indolium iodide 5-7 (8 mmol), a 3,4-dialkoxycyclobut-3-ene-1,2-dione 8-10 (8 mmol), and triethylamine (1.6 mL) was heated at 75 C (11: 0.3 h; 12, 14: 2 h; 13, 15: 1 h). After the reaction was completed, to the mixture were added water (20 mL) and dichloromethane (50 mL). The dichloromethane layer was separated, washed with water (50 mL×3), and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The product was purified by silica gel column chromatography (CH2Cl2 then CH2Cl2/AcOEt=20:1) and recrystallized from hexane. |
With triethylamine; In butan-1-ol; at 70℃; for 1h; | To a solution of 1-octyl-2,3,3-trimethyl-indoleninium iodide (6) (0.4 g, 1.45 mmol) and 3,4-dibutoxycyclobut-3-ene-1,2-dione (8) (0.33 g, 1.45 mmol) in 2.2 mL of n-butanol, 0.29 mL of triethylamine was added dropwise. The resulting mixture was heated at 70 C for 1 h. After removal of solvent, the crude product containing mainly the semisquaraine 9 was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triethylamine; In butan-1-ol; at 75℃; for 0.3h; | General procedure: An alcohol solution (11, 13, 15: BuOH; 12, 14: EtOH, 12 mL) of a 2,3,3-trimethyl-3H-indolium iodide 5-7 (8 mmol), a 3,4-dialkoxycyclobut-3-ene-1,2-dione 8-10 (8 mmol), and triethylamine (1.6 mL) was heated at 75 C (11: 0.3 h; 12, 14: 2 h; 13, 15: 1 h). After the reaction was completed, to the mixture were added water (20 mL) and dichloromethane (50 mL). The dichloromethane layer was separated, washed with water (50 mL×3), and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The product was purified by silica gel column chromatography (CH2Cl2 then CH2Cl2/AcOEt=20:1) and recrystallized from hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With pyridine; In butan-1-ol; for 12h;Reflux; | A mixture of 1-octyl-2,3,3-trimethyl-indoleninium iodide (6) (0.36 g, 1.33 mmol) and 3,4-dibutoxycyclobut-3-ene-1,2-dione (8) (0.15 g, 0.66 mmol) was refluxed in 27 mL of n-butanol:pyridine mixture (1:1, v/v) for 12 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography using silica gel and hexane:ethyl acetate as eluent mixture (9:1) to afford 0.19 g (0.30 mmol, 45% yield) of dye 1 as blue solid with gold lustre; 1H NMR (300 MHz, CDCl3) delta 7.36 (2H, d, J = 7.2 Hz), 7.31 (2H, t, J = 7.8 Hz), 7.14 (2H, t, J = 7.2 Hz), 6.98 (2H, d, J = 7.8 Hz), 5.97 (2H, s), 3.98 (4H, broad s), 1.80 (4H, m), 1.79 (12H, m), 1.27 (20H, m), 0.88 (6H, t, J = 6.6 Hz); 13C NMR (75 MHz, CDCl3) delta 179.7, 170.1, 142.7, 142.4, 127.9, 123.8, 122.4, 109.5, 86.7, 49.4, 43.9, 31.9, 29.5, 29.3, 27.3, 27.2, 22.8, 14.2; IR (KBr, cm-1) 2924, 2854, 1599, 1494, 1454, 1276, 1168, 1082; elemental analysis: calcd. for C42H56N2O2: C, 81.24; H, 9.09; N, 4.51. Found: C, 80.79; H, 9.34; N, 4.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With pyridine; In butan-1-ol; for 12h;Reflux; | A mixture of N-octyl-2-methylbenzothiazolium iodide (7) (0.35 g, 1.33 mmol) and 3,4-dibutoxycyclobut-3-ene-1,2-dione (8) (0.15 g, 0.66 mmol) was refluxed in 27 mL of n-butanol:pyridine mixture (1:1, v/v) for 12 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography using silica gel and ethyl acetate as eluent to afford 0.14 g (0.23 mmol, 34% yield) of dye 3 as blue solid; 1H NMR (300 MHz, CDCl3) delta 7.53 (2H, d, J = 7.5 Hz), 7.36 (2H, t, J = 7.8 Hz), 7.19 (2H, t, J = 7.8 Hz), 7.11 (2H, d, J = 8.1 Hz), 5.88 (2H, s), 4.05 (4H, t, J = 7.8 Hz), 1.79 (4H, m), 1.28 (m, 20H), 0.89 (6H, t, J = 6.3 Hz); 13C NMR (75 MHz, CDCl3) delta 175.5, 159.4, 141.2, 128.8, 127.1, 123.9, 122.2, 111.4, 85.3, 46.3, 31.8, 29.4, 29.3, 27.4, 27.0, 22.7, 14.2; IR (KBr, cm-1) 2923, 2853, 1579, 1451, 1417, 1350, 1227, 1089; elemental analysis: calcd. for C36H44N2O2S2: C, 71.96; H, 7.38; N, 4.66. Found: C, 71.75; H, 7.78; N, 4.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With triethylamine; In butan-1-ol; at 70℃; for 1h; | In a round bottom flask fitted with condenser compound 4 (1.50 g, 4 mmol), <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (5) (900 mg, 4 mmol) and triethylamine (1.0 mL) were dissolved in butanol (20 mL). Reaction mixture was heated at 70 C for 1 h leading to green solution. Solvent was removed at rotary evaporator and product was purified by column chromatography (silica gel) with ethyl acetate and hexane as eluent giving 740 mg of orange colored solid compound in 48% yield and 98% purity as confirmed by HPLC. Mp 244 C (dec). HR-FAB-mass (calculated 384.1766 for (M+1); measured 384.1790). 1H NMR (500 MHz, CDCl3): deltaH 8.10 (dd, J=1.5, 1.5 Hz, 1H), 7.98 (d, J=2 Hz, 1H), 6.90 (d, J=8.5 Hz, 1H), 5.50 (s, 1H), 4.90 (m, 2H), 3.91 (q, 2H), 3.50 (t, 2H), 1.66 (s, 6H), 1.54 (m, 2H), 1.36 (t, 3H), 1.21 (t, 3H). 13C NMR (500 MHz, CDCl3): delta 192.4, 192.2, 188.79, 188.63, 188.5, 173.7, 173.4, 171.2, 167.0, 166.9, 146.9, 146.9, 141.0, 140.9, 131.6, 123.9, 123.1, 107.5, 82.9, 82.8, 74.2, 70.31, 65.8, 47.4, 47.3, 37.9, 31.1, 29.7, 26.9, 26.9, 18.7, 15.9, 15.3, 13.7, 11.3. FTIR (KBr, cm-1): 3054, 2965, 2580, 2513, 1773, 1715, 1680, 1582, 1540, 1363, 1296, 1207, 1118, 1053, 934, 818, 778, 668, 626. Anal. Calcd for C22H25NO5: C, 68.91%; H, 6.57%; N, 3.65; found: C, 68.84%; H, 6.49%; N, 3.69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triethylamine; In butan-1-ol; at 70℃; for 1h; | In a round bottom flask fitted with condenser, compound 1 (2.99 g, 10 mmol), <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (2.24 g, 10 mmol) and 2 mL of triethylamine were dissolved in butanol (10 mL). Reaction mixture was heated at 70 C for 1 h leading to green solution. Solvent was removed under vacuum and product was purified by column chromatography (silica gel) with ethyl acetate and hexane as eluent giving 1.73 g orange colored solid compound in 53% yield and 99% purity as confirmed by HPLC. Mp 248 C (dec). HR-FAB-mass (calculated 324.1555 for (M+1); measured 324.1605). 1H NMR (500 MHz, CDCl3): deltaH 7.54 (t, 1H), 7.48 (dd, J=1.5, 1.5 Hz, 1H), 7.36 (dd, J=10.5, 8.5 Hz, 3H), 7.23 (t, 1H), 5.28 (s, 1H), 4.82 (t, 2H), 4.21 (m, 2H), 1.85 (m, 2H), 1.50 (m, 5H), 1.00 (t, 3H). 13C NMR (500 MHz, CDCl3): delta 185.0, 173.8, 150.4, 139.13, 132.9, 131.1, 128.8, 124.2, 123.9, 113.9, 85.6, 73.5, 42.7, 32.2, 18.7, 13.8, 11.5. FTIR (KBr, cm-1): 2956, 2938, 2872, 1762, 1753, 1697, 1628, 1536, 1491, 1457, 1406, 1323, 1186, 1172, 1063, 916, 824, 743. Anal. calcd for C20H21NO3: C, 74.28%; H, 6.55%; N, 4.33; found: C, 74.31%; H, 6.51%; N, 4.29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: A column with ion exchange resin DOWEX 50WX8-100 was filled with hydrochloric acid (300 mL, 1 M) and then washed with distilled water to neutral pH as described in Ref. [19]. Potassium salts 1-3 were dissolved in water and passed through a column with DOWEX 50WX8-100. The solvent was removed under reduced pressure and residue was dried to give protonated forms of the indolenines. Triethylamine (TEA) (1 mL) in ethanol (5 mL) and dibutyl squarate (3 mmol) were added to the solution of the protonated indolenine (2 mmol) in ethanol (25 mL).The mixture was heated under reflux for 4 h. After cooling all volatile components were removed and residue was dissolved in water and passed through a column with DOWEX 50WX8-100 that was prepared as described above. After removing the solvent water (28 mL) and hydrochloric acid (0.4 mL, 1 M) were added to the crude product. The mixture was heated under reflux for 2 h and then column separated (RP-18, water-acetonitrile) to yield monosquaraines as dark yellow powders. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | General procedure: 2.2.2.2. Method B [61]. A mixture of potassium salt (2 mmol), dibutyl squarate (3 mmol) and pyridine (15 mL) was stirred for 6 h at 100 C. The product was hydrolyzed and purified according to the Method A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: A column with ion exchange resin DOWEX 50WX8-100 was filled with hydrochloric acid (300 mL, 1 M) and then washed with distilled water to neutral pH as described in Ref. [19]. Potassium salts 1-3 were dissolved in water and passed through a column with DOWEX 50WX8-100. The solvent was removed under reduced pressure and residue was dried to give protonated forms of the indolenines. Triethylamine (TEA) (1 mL) in ethanol (5 mL) and dibutyl squarate (3 mmol) were added to the solution of the protonated indolenine (2 mmol) in ethanol (25 mL).The mixture was heated under reflux for 4 h. After cooling all volatile components were removed and residue was dissolved in water and passed through a column with DOWEX 50WX8-100 that was prepared as described above. After removing the solvent water (28 mL) and hydrochloric acid (0.4 mL, 1 M) were added to the crude product. The mixture was heated under reflux for 2 h and then column separated (RP-18, water-acetonitrile) to yield monosquaraines as dark yellow powders. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol; at 20℃; for 24h; | General procedure: A reaction mixture of the appropriate 4-aminoquinoline (1eq.) and <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (1eq.) in dry methanol (2ml for 0.22mmol of amine) was stirred at room temperature for 24h. The solvent was then removed under reduced pressure and the obtained residue was recrystallized from MeOH/EtOAc affording the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In methanol; for 12h;Reflux; | General procedure: A reaction mixture of the appropriate 4-aminoquinoline (2eq.) and <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (1eq.) in dry methanol (2ml for 0.22mmol of amine) was heated at reflux for 12h. The solvent was then removed under reduced pressure, and the obtained residue recrystallized from MeOH/EtOAc affording the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In methanol; at 20℃; for 24h; | General procedure: A reaction mixture of the appropriate 4-aminoquinoline (1eq.) and <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (1eq.) in dry methanol (2ml for 0.22mmol of amine) was stirred at room temperature for 24h. The solvent was then removed under reduced pressure and the obtained residue was recrystallized from MeOH/EtOAc affording the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In methanol; for 12h;Reflux; | General procedure: A reaction mixture of the appropriate 4-aminoquinoline (2eq.) and <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (1eq.) in dry methanol (2ml for 0.22mmol of amine) was heated at reflux for 12h. The solvent was then removed under reduced pressure, and the obtained residue recrystallized from MeOH/EtOAc affording the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol; for 48h;Reflux; | General procedure: A reaction mixture of the appropriate 4-aminoquinoline (2eq.) and <strong>[2892-62-8]3,4-dibutoxy-3-cyclobutene-1,2-dione</strong> (1eq.) in dry methanol (2ml for 0.22mmol of amine) was heated at refluxed for 48h. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica gel using as eluent n-hexane/EtOAc (7:3) to EtOAc (100%) affording the corresponding product. |
Tags: 2892-62-8 synthesis path| 2892-62-8 SDS| 2892-62-8 COA| 2892-62-8 purity| 2892-62-8 application| 2892-62-8 NMR| 2892-62-8 COA| 2892-62-8 structure
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H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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