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CAS No. : | 34114-12-0 | MDL No. : | MFCD06345720 |
Formula : | C8H6N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GEKBULKUEADYRB-UHFFFAOYSA-N |
M.W : | 190.16 | Pubchem ID : | 323168 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.57 |
TPSA : | 91.76 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) : | -6.93 cm/s |
Log Po/w (iLOGP) : | 0.39 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | 0.56 |
Log Po/w (MLOGP) : | 1.07 |
Log Po/w (SILICOS-IT) : | 0.91 |
Consensus Log Po/w : | 0.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.93 |
Solubility : | 2.21 mg/ml ; 0.0116 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.25 |
Solubility : | 1.08 mg/ml ; 0.00567 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.38 |
Solubility : | 0.785 mg/ml ; 0.00413 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
Signal Word: | Danger | Class: | 4.1 |
Precautionary Statements: | P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | 1325 |
Hazard Statements: | H315-H319-H228 | Packing Group: | Ⅲ |
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 |
---|---|---|
98% | at 105℃; for 5 h; Sealed tube; Green chemistry | General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 °C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product. |
78% | With bismuth(III) chloride; sodium azide In water; isopropyl alcohol at 160℃; for 1 h; Microwave irradiation | General procedure: 2-Furonitrile 1m (186 mg, 2 mmol), NaN3 (260 mg, 4 mmol), BiCl3 (126 mg, 0.4 mmol), and 8 mL of a 3:1 isopropanol/water mixture were added to a 30-mL Pyrex microwave vessel, which was then capped. The microwave vessel was then placed in a Milestone Start Synth microwave reactor. The reaction was magnetically stirred and heated for 1 h at 150°C. The reaction was monitored by thin-layer chromatography (TLC) using an ether/hexane mixture (typically 50/50) for development. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate (20 mL) and was hed with ethyl acetate (2×15 mL). The aqueous sodium bicarbonate layer was cooled with ice and acidified to a pH of 2 or less with concentrated hydrochloric acid, which was added dropwise. The precipitate formed was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried with anhydrous sodium sulfate and decanted into a tared round-bottom flask. The organic layer was concentrated under reduced pressure by rotary evaporation at 40°C and then under high vacuum. The tetrazole product was recrystallized from ethyl acetate and hexane. |
71% | With sodium azide In N,N-dimethyl-formamide at 120℃; for 16 h; | General procedure: In a round-bottom flask, 0.2 g benzonitrile (2 mmol) and0.4 g sodium azide (6 mmol), were added to 10 mL DMF.To this mixture, 20 mg of functionalized KIT-6 was addedand the reaction mixture was refluxed. The progress ofreaction was monitored by TLC (75:25 ethyl acetate/nhexane).After completion of the reaction, the reactionmixture was cooled and filtered. The solid materials werewashed three times with acetone and then with the water.The catalyst was collected and dried to activation for nextrun. The product was obtained by acidification of solutionwith hydrochloric acid (5 mL, 6 M). The precipitate wasfiltered and recrystallized from a water/ethanol mixture toget pure product as a white powder, yield: 88percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 298℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 298℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 298℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 298℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4-Carboxy-benzonitril, NaN3, LiCl in sd. Aethylenglykol-monomethylaether; | ||
Entspr. Benzonitril, Ammoniumazid.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 4-(1H-tetrazole-5-yl)benzoate With methanol; sodium hydroxide; water at 20℃; for 2h; Stage #2: With hydrogenchloride In water | A mixture of 4-cyano-benzoic acid methyl ester (4.02 g, 25 mmol), sodium azide (32.5 mmol) and triethylamine hydrochloride (32.5 mmol) in toluene (40 mL) is heated at 970C for 7 hours. After cooling the solution, water (100 mL) was added. The aqueous phase was separated and to this solution HCl cone (7 g) was added. A precipitate formed which was isolated by filtration and washed with water. The obtained solid was suspended in aq. NaOH solution (20 mL, 10% w/w) and methanol (20 mL) and left stirring at room temperature for 2 hours. The solvent was then evaporated, water was added to the residue and the pH acidified with HCl (6M). A white precipitate formed which was isolated by filtration, washed with water and dried under vacuum to give the title compound (4.5 g, 95%). 1H-NMR (dmso-d6) δ 8.09-8.17 (m, 4H); (M+ 1) e/z 191 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In <i>N</i>-methyl-acetamide | 20 2-(1'-Iodopropyn-3'-yl)-5-(p-carboxyphenyl)tetrazole (Compound No. 38) EXAMPLE 20 2-(1'-Iodopropyn-3'-yl)-5-(p-carboxyphenyl)tetrazole (Compound No. 38) Following the same procedures as in Example 8 except that 0.92 g (5 mmoles) of 5-(p-carboxyphenyl)tetrazole and an equimolar amount of the same reagent were used and the reaction was conducted in 5 ml of dimethylformamide, there were prepared 1.15 g (65%) of the crude crystalline product. This product was subjected to a silica gel column chromatography (solvent system: ethyl acetate) to isolate only the substance having Rf value of 0.66 by a silica gel TLC using ethyl acetate, i.e. pure 2-(1'-iodopropyn-3'-yl)-5-(p-carboxyphenyl)tetrazole, 438 mg (25%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-(1H-tetrazol-5-yl)benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride In N,N-dimethyl-formamide at 20℃; | 26 Example 26 N-{2-[4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-(1H-tetrazol-5-yl)-benzamide DIPEA (200 mg, 0.27 mL, 1.5 mmol) was added to a stirred solution of 4-(1H-tetrazol-5-yl)-benzoic acid (100 mg, 0.52 mmol) in DMF (2 mL). HOBT (85 mg, 0.63 mmol) and EDCI (121 mg, 0.63 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride (233 mg, 0.63 mmol) (prepared according to a procedure similar to that described in Synthesis Procedure 1, using 5-fluoro-2-(trifluoromethyl)benzoic acid (Aldrich, St. Louis, Mo.) as a starting material) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with ethyl acetate. The organic layer was washed with saturated brine solution and dried over sodium sulfate. The organic layer collected was concentrated under reduced pressure to afford 169 mg (64%) of N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-(1H-tetrazol-5-yl)-benzamide. LCMS Purity: 91.03%. 1H NMR (DMSO-d6): δ 8.8 (bt, 1H), 8.2-8.0 (m, 4H), 8.0-7.9 (m, 1H), 7.6-7.5 (m, 2H), 4.3-4.1 (m, 2H), 3.8-3.4 (m, 6H), 3.3-3.0 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium azide; tetrabutylammomium bromide at 105℃; for 5h; Sealed tube; Green chemistry; | 4-(1H-Tetrazol-5-yl)benzoic acid24 (2c) Table 2, entry 2 General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 °C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product. |
82% | With sodium azide; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 120℃; for 24h; | |
80% | With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 120℃; for 24h; |
79% | With sodium azide; water; zinc(II) chloride at 25℃; for 24h; Micellar solution; | |
79% | With sodium azide; zinc(II) chloride In water at 25℃; for 24h; | |
78% | With bismuth(III) chloride; sodium azide In water; isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | Typical ExperimentalMethodology: Synthesisof5-(Furan-2-yl)-1Htetrazole (2m) General procedure: 2-Furonitrile 1m (186 mg, 2 mmol), NaN3 (260 mg, 4 mmol), BiCl3 (126 mg, 0.4 mmol), and 8 mL of a 3:1 isopropanol/water mixture were added to a 30-mL Pyrex microwave vessel, which was then capped. The microwave vessel was then placed in a Milestone Start Synth microwave reactor. The reaction was magnetically stirred and heated for 1 h at 150°C. The reaction was monitored by thin-layer chromatography (TLC) using an ether/hexane mixture (typically 50/50) for development. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate (20 mL) and was hed with ethyl acetate (2×15 mL). The aqueous sodium bicarbonate layer was cooled with ice and acidified to a pH of 2 or less with concentrated hydrochloric acid, which was added dropwise. The precipitate formed was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried with anhydrous sodium sulfate and decanted into a tared round-bottom flask. The organic layer was concentrated under reduced pressure by rotary evaporation at 40°C and then under high vacuum. The tetrazole product was recrystallized from ethyl acetate and hexane. |
77% | With sodium azide; betaine; zinc(II) chloride In water at 20℃; for 15h; | 3 Preparation of 5-(4-carboxyphenyl)-1H-tetrazole After mixing 4-cyanobenzoic acid 140 mg (0.94 mmol), sodium azide 74 mg (1.12 mmol), zinc chloride 128 mg (0.94 mmol), betaine 12 mg (0.09 mmol) and adding 3 ml of water , The mixture was stirred at room temperature for 15 hours. After completion of the reaction, about 1 ml of 3N hydrochloric acid aqueous solution was added to adjust the pH to 2-3, and the resulting white solid was filtered. The filtrate was dried to give about 138 mg of 5-(4-carboxyphenyl)-1H-tetrazole (yield 77%). |
71% | With sodium azide In N,N-dimethyl-formamide at 120℃; for 16h; | General procedure for the synthesis of aryltetrazoles General procedure: In a round-bottom flask, 0.2 g benzonitrile (2 mmol) and0.4 g sodium azide (6 mmol), were added to 10 mL DMF.To this mixture, 20 mg of functionalized KIT-6 was addedand the reaction mixture was refluxed. The progress ofreaction was monitored by TLC (75:25 ethyl acetate/nhexane).After completion of the reaction, the reactionmixture was cooled and filtered. The solid materials werewashed three times with acetone and then with the water.The catalyst was collected and dried to activation for nextrun. The product was obtained by acidification of solutionwith hydrochloric acid (5 mL, 6 M). The precipitate wasfiltered and recrystallized from a water/ethanol mixture toget pure product as a white powder, yield: 88%. |
70% | With sodium azide In N,N-dimethyl-formamide at 100℃; for 12h; | |
64% | With sodium azide In N,N-dimethyl-formamide for 24h; Reflux; | |
64% | With sodium azide In N,N-dimethyl-formamide at 110 - 120℃; for 24h; | |
63% | With trimethylsilylazide at 140℃; for 4h; Sealed tube; | |
63.15% | With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 120℃; for 12h; | |
With sodium azide; zinc dibromide In water for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.2% | at 120℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium hydroxide In water at 180℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 72 h / 120 °C 2.1: ethanol / 1 h / Inert atmosphere; Reflux 2.2: 4 h / Inert atmosphere; Reflux 2.3: 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 72 h / 120 °C 2.1: ethanol / 1 h / Inert atmosphere; Reflux 2.2: 4 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 72 h / 120 °C 2.1: ethanol / 1 h / Inert atmosphere; Reflux 2.2: 4 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 72 h / 120 °C 2.1: ethanol / 1 h / Inert atmosphere; Reflux 2.2: 4 h / Inert atmosphere; Reflux 2.3: 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid at 120℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol at 65℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6.0h; | General procedure: A solution of <strong>[883535-89-5]2-(2-methyl-1H-indol-1-yl)ethanamine</strong> (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL×3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With nitric acid In methanol at 85℃; for 36h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.2% | With nitric acid at 105℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tetrafluoroboric acid In water at 120℃; for 36h; Sealed tube; High pressure; | |
50% | With tetrafluoroboric acid In water at 120℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tetrafluoroboric acid at 120℃; for 48h; Sealed tube; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tetrafluoroboric acid at 120℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrafluoroboric acid In water at 120℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.6% | With nitric acid at 105℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.2% | at 115℃; for 72h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; N,N-dimethyl-formamide at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.61% | In methanol; N,N-dimethyl-formamide at 130℃; for 72h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.1% | In methanol; N,N-dimethyl acetamide; water at 85℃; for 24h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: manganese(II) chloride tetrahydrate; ammonium formate; water; 4-(1H-tetrazol-5-yl)benzoic acid; N,N-dimethyl-formamide Sonication; Stage #2: at 120℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With tetrafluoroboric acid at 120℃; for 90h; Sealed tube; | 2.2 Synthesis of {(NH2Me2)[Cd3(μ3-OH) (tpt) (TZB)3](H2O)2(1,4-dioxane)5}n (1) A mixture of Cd(NO3)2·4H2O (62mg, 0.2mmol), H2TZB (19mg, 0.1mmol), tpt (32mg, 0.1mmol) was dissolved in a mixed solvent of DMA/1,4-dioxane/H2O (8mL, V:V:V=1:2:1). After the addition of HBF4 (4 drops, 50% in aq), the mixture was sealed in a 25mL Teflon-lined stainless steel container and heated to 120°C with a period of 30h, and then kept a 120°C for 60h under autogenous pressure. After the reactor was cooled to room temperature with a period of 30h, a large amount of colorless polyhedral crystals were obtained. The yield was 47% for 1 based on the tpt ligand. Anal. Calcd for C64H83Cd3N19O19 (1): C, 43.68; H, 4.75; N, 15.12; %. Found for: C, 43.84; H, 4.31; N, 14.85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: 4-(1H-tetrazol-5-yl)benzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1.5h; Inert atmosphere; Stage #2: 3-fluoro-4-[4-(pyridin-2-yl)piperazin-1-yl]aniline In acetonitrile at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-(1H-tetrazol-5-yl)benzoic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N-(3,5-dimethylphenyl)-6-[(2R,4R)-2-methyl-4-piperidyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-amine In N,N-dimethyl-formamide at 20℃; for 3h; | 1.78 1.78. Cpd 153 To a solution of 4-(1H-tetrazol-5-yl)benzoic acid (CAS 34114-12-0; 57 mg, 0.30 mmol, 1.0 eq.) in DMF (4 mL)were added TEA (164 mL, 1.18 mmol, 4.0 eq.) and HATU (153 mg, 0.30 mmol, 1.0 eq.), the mixture was stirred at RTfor 30 min and Int 39 (80 mg, 0.24 mmol, 1.0 eq.) was added. The reaction mixture was stirred at RT for 3 h. The reactionmedium was quenched with a sat. NaHCO3 aq. solution and the pH was adjusted to 4 with a 1N HCl aq. solution. Theaqueous phase was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and concentratedto dryness. The residue was purified by flash chromatography on silica gel (eluting with DCM/MeOH) andtwice by preparative HPLC to afford Cpd 153. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 135℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; | 20 N-(1-(4-(5-chloro-2-(1 H-tetrazol-1-yl)phenyl)-1 H-1,2,3-triazol-1-yl) Preparation of -3-phenylpropan-2-yl)-4-(1 H-tetrazol-5-yl)benzamide 1-(4-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-1H-1,2,3-triazol-1-yl)-3-phenylpropane-2-amine Hydrochloride (50 mg, 0.12 mmol) was dissolved in dimethylformamide (3 mL) and diisopropylethylamine (0.063 mL, 0.36 mmol), 4-(1H-tetrazol-5-yl)benzoic acid (25 mg , 0.13 mmol) was added and stirred for 2 hours.Distilled water (20 mL) was added to the reaction solvent, followed by extraction with ethyl acetate (20 mL x 2). It was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and recrystallized in diethyl ether (5 mL) to give the title compound (25 mg, 40%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.8% | In ethanol at 115℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 2h; | 2 Synthesis of N-(4-propoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide (A2): 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g, 6.8 mmol) and DMAP (1.3 g, 10.5 mmol) were mixed in 4 mL of dichloromethane and stirred at room temperature 10 minutes.Take another round bottom flask, add 4-(1-hydro-tetrazol-5-yl)benzoic acid (1.0g, 5.6mmol), DMAP (1.3g, 10.5mmol), p-propoxyaniline (1.3g) , 6.8 mmol) was dissolved in 20 mL of a mixed solvent of DMF and DCM (DMF: DCM=1:4), stirred until the solution was clear, and then added the above solution after stirring for 10 minutes.After stirring at 60° C. for 2 hours, 30 mL of dichloromethane and 30 mL of water were added, and the aqueous phase was separated.The aqueous phase was acidified with dilute hydrochloric acid to pH 3, and suction filtered to obtain the crude product.Recrystallization from methanol gave about 0.5 g of N-(4-propoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide as a white solid with a yield of 31%. |
22.4 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
22.4 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 6h; | 3 Synthesis of N-(4-isopropoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide (A3): 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g, 6.8 mmol) and DMAP (1.3 g, 10.5 mmol) were mixed in 4 mL of dichloromethane and stirred at room temperature 10 minutes.Take another round bottom flask, add 4-(1-hydro-tetrazol-5-yl)benzoic acid (1.0g, 5.6mmol), DMAP (1.3g, 10.5mmol), p-isopropoxyaniline (1.0g) g, 6.8 mmol) was dissolved in 20 mL of a mixed solvent of DMF and DCM (DMF: DCM=1:4), stirred until the solution was clear, and then added the above solution after stirring for 10 minutes.After stirring at 25°C for 6 hours, 30 mL of dichloromethane and 30 mL of water were added, and the aqueous phase was separated.The aqueous phase was acidified with dilute hydrochloric acid to pH 3, and suction filtered to obtain the crude product.Recrystallization from methanol gave about 0.8 g of white solid N-(4-isopropoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide with a yield of 46%. |
59.4 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
59.4 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 8h; | 4 Synthesis of N-(4-ethoxybenzyl)-4-(1-hydro-tetrazol-5-yl)benzamide (A4): 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g, 6.8 mmol) and DMAP (1.3 g, 10.5 mmol) were mixed in 4 mL of dichloromethane and stirred at room temperature 10 minutes.Take another round bottom flask, add 4-(1-hydro-tetrazol-5-yl)benzoic acid (1.0 g, 5.6 mmol), DMAP (1.3 g, 10.5 mmol), p-ethoxybenzylamine (1.0 g, 6.8 mmol) was dissolved in 20 mL of a mixed solvent of DMF and DCM (DMF:DCM=1:4), stirred until the solution became clear, and then added the above solution after stirring for 10 minutes.After stirring at 60°C for 8 hours, 30 mL of dichloromethane and 30 mL of water were added, and the aqueous phase was separated.The aqueous phase was acidified with dilute hydrochloric acid to pH 3, and suction filtered to obtain the crude product.Recrystallization from methanol gave about 0.6 g of white solid N-(4-ethoxybenzyl)-4-(1-hydro-tetrazol-5-yl)benzamide with a yield of 37%. |
47.7 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
47.7 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 8h; | 1 Synthesis of N-(4-ethoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide (A1): 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g, 6.8 mmol) and DMAP (1.3 g, 10.1 mmol) were mixed in 4 mL of dichloromethane and stirred at room temperature 10 minutes.Take another round bottom flask, add 4-(1-hydro-tetrazol-5-yl)benzoic acid (1.0 g, 5.6 mmol), DMAP (1.3 g, 10.1 mmol), p-ethoxyaniline (0.9 g) , 6.8 mmol) was dissolved in 20 mL of a mixed solvent of DMF and DCM (DMF: DCM=1:4), stirred until the solution was clear, and then added the above solution after stirring for 10 minutes.After stirring at 25°C for 8 hours, 30 mL of dichloromethane and 30 mL of water were added, and the aqueous phase was separated.The aqueous phase was acidified with dilute hydrochloric acid to pH 3, and suction filtered to obtain the crude product.Recrystallization from methanol gave about 0.6 g of white solid N-(4-ethoxyphenyl)-4-(1-hydro-tetrazol-5-yl)benzamide with a yield of 37%. |
49.8 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
49.8 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.5 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). 4.1.3.1. N-(4-chlorophenyl)-4-(1H-tetrazol-5-yl)benzamide (IIIa). Whitesolid (yield: 30.5%); Melting point: 293.9 C. 1H NMR (400 MHz,DMSO-d6) 10.55 (s, 1H), 8.19 (q, J = 8.4 Hz, 4H), 7.85 (d, J = 8.9 Hz,1H), 7.44 (d, J = 8.9 Hz, 1H). 13C NMR (151 MHz, DMSO-d6) 165.2,138.3, 137.2, 129.2, 129.0, 128.0, 127.5, 127.4, 122.4. HRMS(ESI):Calcd for C14H9ClN5O [M H]- 298.0496, Found 298.0503. |
30.5 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). 4.1.3.1. N-(4-chlorophenyl)-4-(1H-tetrazol-5-yl)benzamide (IIIa). Whitesolid (yield: 30.5%); Melting point: 293.9 C. 1H NMR (400 MHz,DMSO-d6) 10.55 (s, 1H), 8.19 (q, J = 8.4 Hz, 4H), 7.85 (d, J = 8.9 Hz,1H), 7.44 (d, J = 8.9 Hz, 1H). 13C NMR (151 MHz, DMSO-d6) 165.2,138.3, 137.2, 129.2, 129.0, 128.0, 127.5, 127.4, 122.4. HRMS(ESI):Calcd for C14H9ClN5O [M H]- 298.0496, Found 298.0503. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37.7 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
37.7 % | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; | 4.1.3. General procedure for preparation of compounds IIIa-f General procedure: 1-ethyl-(3-dimethylaminopropyl) carbon diimine hydrochloride(0.68 mmol) and 4-dimethylaminopyridine (1.01 mmol) were mixed in5 mL of CH2Cl2 and stirred for 10 min at room temperature. To anotherround-bottom flask was added 1-(4-carboxyphenyl)-1H-tetrazole (5;0.56 mmol), 4-dimethylaminopyridine (1.01 mmol), 4-ethoxyaniline(0.68 mmol), and 20 mL of mixed solvent (dimethylformamide:CH2Cl2 (v/v) = 1:4). Stirred the solution until it was clarified. Theaforementioned solution was added, followed by stirring for 6 h at 60 C.CH2Cl2 (30 mL) and water (30 mL) were added to separate the aqueousphase. The water phase was acidified with dilute hydrochloric acid to pH3, then pumped and filtered to obtain a crude product. The crudeproduct was purified by recrystallization in CH3OH. The filter cakes ofIIIb, IIIc and IIIe were washed by CH2Cl2 and purified by flash columnchromatography (V(CH2Cl2): V(CH3OH) = 100: 1, 0.1% acetic acid). Butthe remaining compounds were purified by flash column chromatography(16.7% ethyl acetate and 0.1% acetic acid in petroleum ether). |
Tags: 34114-12-0 synthesis path| 34114-12-0 SDS| 34114-12-0 COA| 34114-12-0 purity| 34114-12-0 application| 34114-12-0 NMR| 34114-12-0 COA| 34114-12-0 structure
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P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
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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