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CAS No. : | 16370-63-1 |
Formula : | C5H8N4O2 |
M.W : | 156.14 |
SMILES Code : | COC1=NC(=NC(=N1)OC)N |
MDL No. : | MFCD00052765 |
InChI Key : | KVHFZZUPCXCRIX-UHFFFAOYSA-N |
Pubchem ID : | 27840 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.22 |
TPSA ? Topological Polar Surface Area: Calculated from | 83.15 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.74 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.24 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | -0.52 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | -1.46 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | -0.05 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.23 |
Solubility | 9.17 mg/ml ; 0.0588 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.55 |
Solubility | 4.44 mg/ml ; 0.0284 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.16 |
Solubility | 10.8 mg/ml ; 0.0689 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.08 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 2.59 |
* 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 |
---|---|---|
86% | With ammonia In water at 25 - 51℃; for 2 h; | Example 3A Preparation of 2-amino-4,6-dimethoxy-1,3,5-triazine precursor A mixture of 10.1 g (0.059 mole) of 2,4,6-trimethoxy-1,3,5-triazine and water (100 mL) was stirred at 25° C. while 110 mL of 28percent aqueous ammonia was added. The mixture was held at 48-51° C. for two hours before it was cooled to 25° C. and the insoluble white crystals were removed. The product was washed with water and dried to give 7.84 g (86percent), mp 218-221° C. 1H NMR (DMSO-d): 3.81 (s, 6H); 7.38 (s, 2H). 13C NMR (DMSO-d6): 53.9, 169.0, 171.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.4% | With ammonia; sodium methylate In methanol; water; toluene | EXAMPLE 2 There is added to the atmosphere above the reaction mixture 5.1 g (0.299 moles) of ammonia gas over a 25 minute period at 20° to 40° C., to a mixture of 26.8 g (0.145 moles) of cyanuric chloride and 100 g of toluene. The mixture is cooled to 10° C. and 25 g of methanol is added. There is then added over a five minute period, 99.0 g of a 25percent solution of sodium methoxide to the resulting mixture causing it to reflux. The mixture is kept under reflux for 15 minutes; there is then added 100 g of water. A white solid is obtained after the mixture is filtered and washed with 50 g of water. After drying at 80° C. for several hours, 20.3 g of a white solid is obtained. Based on method of preparation, there is obtained an 85.4percent yield of 2-amino-4,6-dimethoxy-1,3,5-triazine (ADMT) based on cyanuric chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With pyridine; In dichloromethane; acetonitrile; at 20 - 60℃; for 21.0h;molecular sieve; | At 55-60 C. and under argon, a solution of 5.0 g (17.9 mmol) of methyl 2-chlorosulfonyl-6-nitrobenzoate in 55 ml of dry dichloromethane is added dropwise over 2 h to a suspension of 2.79 g (17.9 mmol) of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong>, 1.28 g (19.7 mmol) of sodium cyanate, 1.45 ml (17.9 mmol) of pyridine and 500 mg of freshly activated molecular sieve (pore size 3 ) in 85 ml of dry acetonitrile. After 7 h of stirring at this temperature, the mixture is allowed to warm to room temperature. After a further 12 h, the reaction mixture is concentrated and the residue is suspended in 200 ml of water and adjusted to pH 10 using 2 N aqueous sodium hydroxide solution. The precipitated solid is filtered off with suction and the filtrate is extracted with ethyl acetate. The organic phase is separated off and the aqueous phase is adjusted to pH 1.5 using 3 N aqueous hydrochloric acid solution and stirred in an ice bath for 15 min. The precipitated solid is then filtered off with suction, washed first with water and then with methanol and dried under reduced pressure. This gives 2.88 g (36% of theory) of methyl 2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]-6-nitrobenzoate of m.p. 185-195 C. (decomp.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrazine; In water; at 25 - 125℃; for 3.0h;Heating / reflux; | Example 3B; Preparation of 2-amino-4,6-dihydrazino-1,3,5-triazine Percursor; 00025] A mixture of 8.1 g (0.052 mole) of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> and water (103 mL) was stirred at 25C. while 77 mL of hydrazine monohydrate was added The mixture was held at 120-125C. (slow reflux) for three hours. The mixture was cooled to 25C. and the insoluble white crystals were removed, washed first with water and then ethanol, and dried to give 8.0 g (98%), mp 290C., dec. NMR analysis indicated the product was very pure (no impurity peaks could be detected). 1H NMR (DMSO-d6): 4.05 (s, 4H); 6.22 (s, 2H); 7.63 (s, 2H). 13C NMR (DMSO-4): 166.3, 167.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; hydrogenchloride; In water; | Example (IV-1) 70 g (0.44 mol) of phenyl chloroformate are added dropwise with stirring to a mixture of 31 g (0.20 mol) of <strong>[16370-63-1]2-amino-4,6-dimethoxy-s-triazine</strong> and 100 ml of pyridine. The reaction mixture is stirred at 20 C. to 25 C. for about 15 hours and subsequently concentrated using water pump vacuum. The residue is taken up in water and then acidified using conc. hydrochloric acid. The resulting crystalline product is isolated by filtration with suction. This gives 74.2 g (91% of theory) of 2-(N,N-bis-phenoxycarbonyl-amino)-4,6-dimethoxy-s-triazine of melting point 125 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In N,N-dimethyl acetamide; | EXAMPLE 1 The Preparation of phenyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate Into 50 ml Erlenmeyer flask, were added <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> 2.00 g (0.0128 mole) and dry N,N-dimethylacetamide 18 ml and stirred in the suspended condition. To the suspended mixture, at the room temperature, was added 60% oily sodium hydride 0.51 g (0.0128 mole). The reaction mixture was homogeneous after vigorous evolution of hydrogen gas. A solution of diphenyl carbonate 2.74 g (0.0128 mole) and dry N,N-dimethylacetamide was subsequently added to the mixture under the water cooling during 10 minutes, and stirred for further 10 minutes. The reaction mixture was poured into 20 ml iced water containing 1.4 ml hydrogen chloride (35% aq soln). The precipitate was filtered off and wash with iced water and then petroleum ether. After being air-dried, the product was obtained. The obtained amount (yield of theory) and the physical property were showed hereinafter. 2.60 g (73.5% of theory) mp. 141-142 C. IR (KBr,cm-1) 3304, 1780, 1752, 1618, 1482 1390, 1360, 1290, 1192 NMR (CDCl3, delta) 4.0(6H, s, OCH3 *2)7.05-7.5(5H, m, Aromatic H) 8.28-8.7(1H, bs, NH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.4% | With ammonia; sodium methylate; In methanol; water; toluene; | EXAMPLE 2 There is added to the atmosphere above the reaction mixture 5.1 g (0.299 moles) of ammonia gas over a 25 minute period at 20 to 40 C., to a mixture of 26.8 g (0.145 moles) of cyanuric chloride and 100 g of toluene. The mixture is cooled to 10 C. and 25 g of methanol is added. There is then added over a five minute period, 99.0 g of a 25% solution of sodium methoxide to the resulting mixture causing it to reflux. The mixture is kept under reflux for 15 minutes; there is then added 100 g of water. A white solid is obtained after the mixture is filtered and washed with 50 g of water. After drying at 80 C. for several hours, 20.3 g of a white solid is obtained. Based on method of preparation, there is obtained an 85.4% yield of 2-amino-4,6-dimethoxy-1,3,5-triazine (ADMT) based on cyanuric chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; N,N-dimethyl-formamide; acetone; | EXAMPLE 2 beta-Methoxyethyl 6-fluoro-2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate 7.1 g of beta-methoxyethyl 6-fluoro-2-isocyanatosulfonylbenzoate in 20 ml of methylene chloride were added over 10 minutes at 25 C. to a stirred mixture of 4 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> in 40 ml of DMF under nitrogen; the temperature rose to 32 C. After the mixture had been stirred for 14 hours at 25 C., the solvent was removed under reduced pressure and the residue was stirred with ether and twice with 3N HCL. It was then taken up in acetone, insoluble mater was separated off and the filtrate was concentrated to dryness. 7 g of the compound shown in the title, of melting point 179 C.-182 C. were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; water; | EXAMPLE 6 Synthesis of an intermediate of general formula (II) 15.6 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> were suspended in 300 ml of dimethylformamide, and 4 g of sodium hydride (oily, 60%) were added to the suspension. The mixture was stirred at room temperature for 1 hour. Furthermore, 33.7 g of dimethyl N-(2-biphenylylsulfonyl)carbonimidodithioate were added, and the mixture was stirred at room temperature for a day and night. The reaction mixture was poured into 2 liters of water and filtered. The filtrate was made weakly acidic to precipitate white crystals. The crystals were collected by filtration and recrystallized from ethanol to give 36.2 g of 1-(2-biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl) 2-methylisothiourea (compound No. II-1), the same compound as obtained in Example 5. The melting point of the product was 135 to 137 C. It was confirmed that by substantially the same procedure as in Example 6 above, compounds Nos. II-2, II-3 and II-4 could be easily synthesised. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | EXAMPLE 2 Phenyl N-(2-biphenylylsulfonyl)carbamate (35.3 g) and <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> (15.6 g) were added to dioxane (200 ml), and the mixture was refluxed with stirring for 2 hours. The reaction mixture was cooled to room temperature and the precipitated crystals were collected by filtration. The crystals were washed with diethyl ether and dried to give the desired 1-(2-biphenylylsulfonyl)3-(4,6-dimethoxytriazin-2-yl)urea (36 g) represented by the following formula. m.p. 175-180 C. STR12 The biological effect of the compound A synthesised in Example 2 is illustrated in the following Example 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; | EXAMPLE 4 Synthesis of an intermediate of general formula (VI) 15.6 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> were suspended in 300 ml of dry toluene, and 27.5 g of 2-phenylbenzenesulfonyl isothiocyanate were added. The mixture was heated under reflux for 8 hours. After cooling, the resulting precipitate was collected by filtration and recrystallized from ethanol to give 35 g of 1-(2-biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)thiourea represented by the following formula: STR28 Melting point: 192-193 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; 1,2-dichloro-ethane; | EXAMPLE 8 Methyl 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)-aminocarbonyl]aminosulfonyl]-4-ethoxybenzoate To a slurry of <strong>[16370-63-1]4,6-dimethoxy-1,3,5-triazin-2-amine</strong> (0.46 g, 2.9 mmol) in dry dichloromethane (5 mL) was added a solution of methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate (crude, ca. 1.2 g, 4.2 mmol) in dichloromethane (5 mL). The reaction mixture was heated at reflux for 1.5 hours, during which time the solid dissolved. On stirring at room temperature overnight a new solid formed. The solvent was rotary evaporated, leaving the crude product as a white solid (1.5 g). This was dissolved in warm 1,2-dichloroethane and chromatographed on a column of silica gel using as eluant 15:1, 10:1, and finally 7:1 dichloromethane-ether, all containing 2 mL/L acetic acid. The appropriate fractions were diluted with toluene and rotary evaporated to give a solid. This was dissolved in minimal warm dichloromethane, diluted with 1-chlorobutane, and rotary evaporated to give a crystalline solid. This was slurried in hexanes, collected, rinsed with 1:1 1-chlorobutane-hexanes and hexanes. and dried. The product was obtained as a white crystalline powder (0.98 g) melting at 181-183 C. PMR (CDCl3, 200 MHz); delta12.15 (slightly broadened s, 1H, SO2 NHCO); 7.89 (d, 1H, H ortho to SO2 NH); 7.77 (d, 1H, H ortho to CO2 CH3); 7.45 (slightly broadened s, 1H, CONH--Het); 7.11 (dd, 1H, H para to SO2 NH); 4.17 (q, 2H, OCH2 CH3); 4.12 (s, 6H, Het--OCH3); 3.90 (s, 3H, CO2 CH3); 1.46 (t, 3H, OCH2 CH3). IR (Nujol): 1730 (vs, ester C=O); 1715 (s, urea C=O) cm-1. | |
In dichloromethane; 1,2-dichloro-ethane; | EXAMPLE 8 Methyl 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)-aminocarbonyl]aminosulfonyl]-4-ethoxybenzoate To a slurry of <strong>[16370-63-1]4,6-dimethoxy-1,3,5-triazin-2-amine</strong> (0.46 g, 2.9 mmol) in dry dichloromethane (5 mL) was added a solution of methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate (crude, ca. 1.2 g, 4.2 mmol) in dichloromethane (5 mL). The reaction mixture was heated at reflux for 1.5 hours, during which time the solid dissolved. On stirring at room temperature overnight a new solid formed. The solvent was rotary evaporated, leaving the crude product as a white solid (1.5 g). This was dissolved in warm 1,2-dichloroethane and chromatographed on a column of silica gel using as eluant 15:1, 10:1, and finally 7:1 dichloromethane-ether, all containing 2 mL/L acetic acid. The appropriate fractions were diluted with toluene and rotary evaporated to give a solid. This was dissolved in minimal warm dichloromethane, diluted with 1-chlorobutane, and rotary evaporated to give a crystalline solid. This was slurried in hexanes, collected, rinsed with 1:1 1-chlorobutane-hexanes and hexanes, and dried. The product was obtained as a white crystalline powder (0.98 g) melting at 181-183 C. PMR (CDCl3, 200 MHz); delta12.15 (slightly broadened s, 1H, SO2 NHCO); 7.89 (d, 1H, H ortho to SO2 NH); 7.77 (d, 1 H, H ortho to CO2 CH3); 7.45 (slightly broadened s, 1H, CONH--Het); 7.11 (dd, 1H, H para to SO2 NH); 4.17 (q, 2H, OCH2 CH3); 4.12 (s, 6H, Het--OCH3); 3.90 (s, 3H, CO2 CH3); 1.46 (t, 3H, OCH2 CH3). IR (Nujol): 1730 (vs, ester C=O); 1715 (s, urea C=O) cm-1. | |
In dichloromethane; 1,2-dichloro-ethane; | EXAMPLE 8 Methyl 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-4-ethoxybenzoate To a slurry of <strong>[16370-63-1]4,6-dimethoxy-1,3,5-triazin-2-amine</strong> (0.46 g, 2.9 mmol) in dry dichloromethane (5 mL) was added a solution of methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate (crude, ca. 1.2 g, 4.2 mmol) in dichloromethane (5 mL). The reaction mixture was heated at reflux for 1.5 hours, during which time the solid dissolved. On stirring at room temperature overnight a new solid formed. The solvent was rotary evaporated, leaving the crude product as a white solid (1.5 g). This was dissolved in warm 1,2-dichloroethane and chromatographed on a column of silica gel using as eluant 15:1, 10:1, and finally 7:1 dichloromethane-ether, all containing 2 mL/L acetic acid. The appropriate fractions were diluted with toluene and rotary evaporated to give a solid. This was dissolved in minimal warm dichloromethane, diluted with 1-chlorobutane, and rotary evaporated to give a crystalline solid. This was slurried in hexanes, collected, rinsed with 1:1 1-chlorobutane-hexanes and hexanes, and dried. The product was obtained as a white crystalline powder (0.98 g) melting at 181-183 C. PMR (CDCl3, 200 MHz): delta12.15 (slightly broadened s, 1H, SO2 MHCO); 7.89 (d, 1H, H ortho to SO2 NH); 7.77 (d, 1H, H ortho to CO2 CH3); 7.45 (slightly broadened s, 1H, CONH-Het); 7.11 (dd, 1H, H para to SO2 NH); 4.17 (q, 2H, OCH2 CH3); 4.12 (s, 6H, Het-OCH3); 3.90 (s, 3H, CO2 CH3); 1.46 (t, 3H, OCH2 CH3). IR (Nujol): 1730 (vs, ester C=O); 1715 (s, urea C=O) cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | EXAMPLE 5 Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate <strong>[16370-63-1]2-Amino-4,6-dimethoxy-1,3,5-triazine</strong> (55.3 g) was added portionwise to 50% sodium hydride (38.0 g) in 1000 ml dry tetrahydrofuran at ambient temperature under nitrogen. After the reaction mixture was stirred for 1.25 hours, dimethylcarbonate (50.0 g) was added dropwise. The reaction mixture was stirred 16 hours at ambient temperature under nitrogen and concentrated hydrochloric acid (68 ml) was slowly added followed by 100 ml tetrahydrofuran. Insoluble material was removed via filtration and discarded. The filtrate was dried and the solvent removed under reduced pressure to give a solid which upon crystallization from ethanol afforded 43.9 g of the tital compound, m.p. 118-122 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diaza-bicyclo-undecene; In water; acetonitrile; | STR93 4.8 g (0.03 mole) of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong>, 10 g (0.03 mole) of 2-(1-methoximinoprop-2-yloxycarbonyl)-phenylsulphonyl isocyanate and 4.5 g (0.03 mole) of diazabicycloundecene (DBU) in 100 ml of acetonitrile are stirred for 20 hours and, for working up, the mixture is poured into 500 ml of water, acidified with concentrated hydrochloric acid and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate and freed from the solvent in vacuo. 2.2 g (24% of theory) of N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-[2-(1-methoximinoprop-2-yloxycarbonyl)-phenylsulphonyl]-urea of melting point 160 C.-168 C. are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; | EXAMPLE 6 N,N-Diethyl-N'-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide A mixture of 0.9 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong>, 2.8 g of the crude sulfonyl isocyanate from Example 4 and a few crystals of DABCO in 25 ml of acetonitrile was stirred at room temperature for 16 hours. A small amount of untreated triazine was filtered off and the filtrate concentrated in-vacuo to a hard glass. Crystallization from methanol gave 0.6 g of N,N-diethyl-N'[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,2-benzenesulfonamide as a white solid, m.p. 175-7. NMR(DMSO-d6)delta: 0.9-1.2 [t, 6.0H, (CH3 CH2)2 N-]; 3.1-3.5 [qt, 4.3H, (CH3 CH2)2 N-]; 3.95 (S, 5.5H, --OCH3 's); 7.9-8.5 (m, 4.1H, 4 aromatics); 11.2 (S, 0.9H, NH); 12.4 (S, 1.1H, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | EXAMPLE 4 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate To a suspension of 0.6 g <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for about 1 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 1.4 g tan solid m.p. 163-166 C. The infrared spectrum shows absorption bands at 1715, 1600, 1550, 1350 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | EXAMPLE 12 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide A mixture of 1.6 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong>, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40 under reduced pressure. The residue was triturated with butyl chloride and filtered to yield the desired compound which melted above 170 with decomposition. | |
In dichloromethane; | EXAMPLE 11 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide A mixture of 1.6 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong>, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate was stirred at ambient temperature for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40 under reduced pressure. The residue was triturated with butyl chloride and filtered to yield the desired compound which melted above 170 with decomposition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | EXAMPLE 10 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbonyl)benzenesulfonamide To 0.7 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> suspended in 5.0 ml anhydrous methylene chloride was added 1.6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 5.0 ml anhydrous methylene chloride. The resulting mixture was filtered to remove some unreacted 2-amino-4,6-dimethoxytriazine, the methylene chloride filtrate was evaporated at reduced pressure and the residue triturated with chlorobutane to yield 0.5 g of desired product melting at 192-195 C. The solid showed infrared absorption peaks at 1705 and 1715 cm-1 consistent for N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbonyl)benzenesulfonamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | EXAMPLE 8 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide To 0.7 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(beta-chloroethoxycarbonyl)benzenesulfonyl isocyanate. After stirring at ambient temperature for sixteen hours the solvent was removed under reduced pressure, the residue triturated with ether and the solid product filtered off, yield 1.21 g m.p. 171-174 C. The solid showed infrared absorption peaks at 1705 and 1715 cm-1, consistent for N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide. | |
In dichloromethane; | EXAMPLE 7 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide To 0.7 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(beta-chloroethoxycarbonyl)benzenesulfonyl isocyanate. After stirring at ambient temperature for sixteen hours the solvent was removed under reduced pressure, the residue triturated with ether and the solid product filtered off, yield 1.21 g, m.p. 171-174 C. The solid showed infrared absorption peaks at 1705 and 1715 cm-1, consistent for N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 10 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzothiophene-3-sulfonamide Using the procedure of Example 3, and substituting 1.6 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> and 2.4 g of benzothiophene-3-sulfonyl isocyanate, a yield of 3.4 g of the desired product was obtained melting at 152. It showed absorption peaks by Nuclear Magnetic Resonance (60 MC) at; 3.95 delta (CH3 O), 7-8 delta (benzohydrogens) and 8.3 delta (thiophene hydrogen) consistent for the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | EXAMPLE 7 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-4-methyl-3-thiophenesulfonamide A solution of 2 g of 4-methyl-3-thiophenesulfonyl isocyanate was added to a suspension of 1.5 g of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> in 20 ml of tetrahydrofuran and the resulting mixture stirred for 16 hours at ambient temperature. The precipitate thus obtained was filtered off and recrystallized to yield 1.5 g of the desired product, m.p. 154-156. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; dichloromethane; | EXAMPLE 2 N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N'-(2-chloro-n-prop-1-yl-sulfonyl)-urea 15.6 g (0.1 mole) of <strong>[16370-63-1]2-amino-4,6-dimethoxy-1,3,5-triazine</strong> were suspended in 150 ml of dichloromethane, and a solution of 19.5 g (0.106 mole) of 2-chloro-n-prop-1-yl-sulfonyl isocyanate in 100 ml of dichloromethane was added at 0 C., while stirring. The mixture was further stirred for 12 hours at room temperature and cooled to 0 C., and 300 ml of n-hexane were added. The precipitated reaction product was filtered off under suction, washed with n-hexane and dried. 30.7 g (90.5% of theory) of N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-chloro-n-prop-1-yl-sulfonyl)-urea of melting point 139-41 C. were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | EXAMPLE 5 Methyl(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate <strong>[16370-63-1]2-Amino-4,6-dimethoxy-1,3,5-triazine</strong> (55.3 g) was added portionwise to 50% sodium hydride (38.0 g) in 1000 ml dry tetrahydrofuran at ambient temperature under nitrogen. After the reaction mixture was stirred for 1.25 hours, dimethylcarbonate (50.0 g) was added dropwise. The reaction mixture was stirred 16 hours at ambient temperature under nitrogen and concentrated hydrochloric acid (68 ml) was slowly added followed by 100 ml tetrahydrofuran. Insoluble material was removed via filtration and discarded. The filtrate was dried and the solvent removed under reduced pressure to give a solid which upon crystallization from ethanol afforded 43.9 g of the title compound, m.p. 118-122 C. |
Tags: 16370-63-1 synthesis path| 16370-63-1 SDS| 16370-63-1 COA| 16370-63-1 purity| 16370-63-1 application| 16370-63-1 NMR| 16370-63-1 COA| 16370-63-1 structure
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