Structure of 13223-43-3
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CAS No. : | 13223-43-3 |
Formula : | C7H9N5O2 |
M.W : | 195.18 |
SMILES Code : | NC1=NN2C(OC)=CC(OC)=NC2=N1 |
MDL No. : | MFCD09033220 |
InChI Key : | SJEIPAUSEWIHJI-UHFFFAOYSA-N |
Pubchem ID : | 11194901 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.17 |
TPSA ? Topological Polar Surface Area: Calculated from |
87.56 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.27 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.19 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.62 |
Solubility | 4.68 mg/ml ; 0.024 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.76 |
Solubility | 3.36 mg/ml ; 0.0172 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.24 |
Solubility | 11.2 mg/ml ; 0.0574 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 |
-7.23 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) |
2.61 |
* 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 |
---|---|---|
91.5% | Stage #1: With hydroxylamine hydrochloride In ethanol at 60℃; for 0.5 h; Stage #2: With triethylamine In ethanol for 5 h; Reflux |
A solution of 3a (114.5 g,0.4 mol) and hydroxylamine hydrochloride (40.3 g, 0.58 mol) in EtOH (600 mL) was stirred vigorously for 0.5 h at 60 C, then triethylamine (58.7 g, 0.58 mol) was added dropwise into the mixture. The resultant mixture was refluxed for 5 h, then cooling to the room temperature. The white solid product of4a was collected by filtration and washed using 200 mL water, yield 71.4 g (91.5percent); |
91.5% | With hydroxylamine hydrochloride; triethylamine In ethanol at 60℃; for 5.5 h; Reflux | In 1000mL equipped with a stirrer, thermometer, reflux condenser, droppingfunnel, 4-neck flask, was added 600mL ethanol, N- (4,6- dimethoxy-pyrimidin-2-yl) -N'-ethoxycarbonyl thiourea 114.5g (0.4mol), hydroxylamine hydrochloride 40.3g (0.58mol),heated to 60 , was added dropwise 58.7g (0.58mol) of triethylamine, 0.5H addition wascomplete, the reaction was refluxed 5H, until starting material N- ( after 4,6-dimethoxy-pyrimidin-2-yl) -N'-ethoxycarbonyl thiourea reaction was complete, cooled toroom temperature filtration and dried 200mL, 50 water washing was stirred 20min,filtered dried to give the product 71.4 g, a purity of 98.6percent, a yield of about 91.5percent. |
82% | With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol | 2. Preparation of 2-amino-5,7-dimethoxy[1,2,4]-triazolo[1,5-a]pyrimidine Ethyl N-[N'-(4,6-dimethoxypyrimidin-2-yl)-thiocarbamoyl]carbamate (0.50 g, 1.7 mmol) was mixed with ethanol (5 mL). To this mixture was added hydroxylamine hydrochloride (0.12 g, 1.7 mmol) and diisopropylethylamine (0.30 mL, 1.7 mmol). The resulting mixture was allowed to stir at room temperature. After 2.5 hours, additional diisopropylethylamine (0.30 mL, 1.7 mmol) was added to the mixture. After 48 hours the ethanol was removed in vacuo and the residue was partitioned between H2O and Et2O to give a powder. The powder was filtered and dried to afford the product as a tan powder (0.27 g, 82percent). mp 215-220° C. 1H NMR (DMSO-d6): δ 6.04 (s, 1H); 5.97 (bs, 2H); 4.04 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.1% | Stage #1: at 78℃; for 5.33333 h; Heating / reflux Stage #2: With hydroxyammonium sulfate In water; ethyl acetate at 71℃; Heating / reflux Stage #3: With sodium carbonate In water; ethyl acetate at 71℃; for 7 h; Heating / reflux |
One pot procedure for the synthesis of 2-amino-5,7-dimethoxy [1,2, 4] triazolopyrimidine (ADTP) from 2-amino-4,6-dimethoxypyrimidine (ADP) 11. 9 g (0.075 mol) ADP was dissolved in 68 g ethyl acetate. 11 g (0.0825 mol) ethoxycarbonyl isothiocyanate was added within 20 min. at 78°C (no exotherm). The mixture was stirred over 5 h at reflux (78-79°C). 49.2 g (0.075 mol) hydroxylammonium sulfate (25 percent solution in water) were added and the mixture heated to 71°C (reflux aceotrope). 50 g (0.1 mol) diluted caustic soda (2 mot/1) was added within 1 h to establish the pH from 1.3 to 6.5 and hold at 6.5-7. 0 (offgas C02 and H2S, slightly exotherm). The mixture was stirred over 6 h under reflux (71°C) for reaction completion. The mixture was cooled down over night to 20°C. The product (ADTP) was filtrated and washed 3 times with each 25 g water to remove the salt (Na content after first wash 0.42 percent, after second 0.20 percent, after third 0.025 percent). Finally the solid ADTP was dried. Yield : 91.1 percent in respect to ADP, purity 95.3 percent (quantitative HPLC assay). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | 2-Amino-5,7-dimethoxy [1,2,4] triazolo [1,5-a] pyrimidine (25.4g, 0.13mol) Add to 137g of dichloromethane, After stirring, 4-dimethylaminopyridine (0.006 g, 0.05 mmol) and 2-methoxy-4-(trifluoromethyl)-pyridine-3-sulfonyl chloride (27.5 g, 0.1 mol), After stirring for 30 minutes, Triethylamine (13.1 g, 0.13 mol) was added dropwise at room temperature. Finally, the temperature was raised to 35 C for 3 h. The mixture was then treated with 4N HCl (60g), was stirred at 25 1 hour, cooled to 10 , filtered, washed with water, washed with methanol and dried to give 40.8 g of pyroxsulam, 94% yield, 98.5% purity (HPLC). | |
82 - 84% | With 3,5-Lutidine; dimethyl sulfoxide; In acetonitrile; at 20℃; for 12h;Product distribution / selectivity; | Example 5 Preparation of N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide 2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine (59 g, 0.30 mol) was combined with 2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride (86 g, 0.31 mol, 1.03 eq) in acetonitrile (210 mL) and 3,5-lutidine (120 g, 93% technical). DMSO (1.3 g, 0.017 mol) was added, and the mixture was stirred at room temperature for 12 hours. The mixture was then treated with 4 N HCl (310 mL), after which the mixture was stirred for another 2 hours at 25 C., then cooled to 10 C. The solids were collected by filtration, washed with a 2:1 v/v solution of water:acetonitrile (160 mL), washed with 95% ethanol (2*80 mL), and dried under vacuum at 100 C. to afford 112 g of product assaying at 98 wt % (84% yield from amine, 82% yield from sulfonyl chloride). |
78% | With 3,5-Lutidine;N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-S,S-dimethyl-sulfilimine hydrochloride salt; In acetonitrile; at 20℃; for 22h;Product distribution / selectivity; | Example 4 Preparation of N-(5,7-dimethoxy[1 2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide 2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine (9.8 g, 0.050 mol) and N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-S,S-dimethyl-sulfilimine hydrochloride salt (1.5 g, 0.005 mol) solids were combined with 2-methoxy-4-(trifluoromethyl)-pyridine-3-sulfonyl chloride (14 g, 0.051 mol) in acetonitrile (40 mL). 3,5-Lutidine (31 g, 93% technical) was added, and the mixture was stirred at room temperature for 22 hours. The mixture was warmed to 42 C. and treated with 3 N HCl (65 mL), after which the mixture was allowed to cool to room temperature over 1.5 hours. The solids were collected by filtration, washed with a 2:1 v/v solution of water:acetonitrile (20 mL), and dried under vacuum at 60 C. to afford 18 g of product assaying at 94 wt % (78% yield). |
Tags: 13223-43-3 synthesis path| 13223-43-3 SDS| 13223-43-3 COA| 13223-43-3 purity| 13223-43-3 application| 13223-43-3 NMR| 13223-43-3 COA| 13223-43-3 structure
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Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL