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CAS No. : | 6377-12-4 | MDL No. : | MFCD00022213 |
Formula : | C12H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LRSYZHFYNDZXMU-UHFFFAOYSA-N |
M.W : | 182.22 | Pubchem ID : | 44621 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 13 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 60.21 |
TPSA : | 41.81 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.49 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | 2.71 |
Log Po/w (WLOGP) : | 2.91 |
Log Po/w (MLOGP) : | 2.17 |
Log Po/w (SILICOS-IT) : | 2.85 |
Consensus Log Po/w : | 2.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.36 |
Solubility : | 0.0788 mg/ml ; 0.000432 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.24 |
Solubility : | 0.105 mg/ml ; 0.000574 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.6 |
Solubility : | 0.00459 mg/ml ; 0.0000252 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P272-P280-P301+P312+P330-P302+P352-P305+P351+P338-P333+P313-P337+P313-P363-P501 | UN#: | N/A |
Hazard Statements: | H302-H317-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 120 - 140℃; | ||
In methanol for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 80℃; for 24h; Inert atmosphere; | 6.2 (2) Synthesis of Intermediate 9H-carbazol-3-amine After 2.122g (0.01mol) 3-nitro-9H-carbazole were added to three 500ml flask, 450ml of absolute ethanol, a magnetic stirrer and argon gas, was heated to 80 deg.] C oil bath, was added 10% wt palladium on carbon 0.1 G, and hydrazine hydrate was gradually added dropwise 4ml, after the reaction was refluxed for 24h, the reaction solution was suction filtered and the filtrate was cold crystallization, the resulting cake was suction filtered and dried in vacuo 80 24h, to give the product 1.731g, 95% yield. This intermediate structure is as follows |
84% | With hydrazine hydrate In ethanol for 2h; Heating; | |
74% | With palladium 10% on activated carbon; hydrazine hydrate In tetrahydrofuran; methanol; ethanol at 60℃; for 1.08333h; | N-R-1-aminocarbazole (5a-5k) and N-R-3-aminocarbazole (6a-6j): General procedure: Pd/C (10%, w/w) (10 mg) was added to the solution of N-R-1-nitrocarbazole or N-R-3-nitrocarbazole (1 mmol, 1a-21a) in 15 ml methanol and 10 mL THF at room temperature. Then the mixture was heated to 60 °C for 10 min. 2 ml of hydraziniumhydroxide in 5 ml ethanol was then added to the solution as dropwise for 5 min. The mixture was vigorously stirred at 60 °C for 60 min and then the Pd/C was ltered off. Subsequent extraction with ethyl ether, distillation and recrystallization with ethanol and THF in vacuum gave white needle crystal (5b and 6b are liquid form). The crystal was dried in N2 flux for 10 min and placed in inertia atmosphere. |
70.3% | With palladium 10% on activated carbon; hydrogen In ethanol for 3h; | Procedure for the synthesis of 9H-carbazol-3-amine (3) A suspension of 3-nitro-9H-carbazole (2, 0.006 mol) and Pd activated carbon (10%) in ethanol was purged with hydrogen gas at 25 psi for 3 h. The reaction mixture was filtered through Celite 545. The filtrate was concentrated under reduced pressure, and the residue was purified through acid-base extraction to obtain the 9H-carbazol-3-amine (3).Yield 70.3 %, ivory solid, mp: 257 , Rf = 0.21 (1:1 n-hexane-ethyl acetate); 1H NMR (400 MHz, DMSO-d6): δH 10.70 (s, NH), 7.88 (d, J = 7.6 Hz, 1H), 7.35 (d, J = 8.4 Hz, 1H), 7.26 (m, 2H), 7.18 (d, J = 8.4Hz, 1H), 7.02(t, J = 8.0 Hz, 1H), 6.75 (dd, J = 2.4, 8.8 Hz, 1H), 4.67 (s, NH). |
70.3% | With palladium 10% on activated carbon; hydrogen In ethanol for 3h; | Procedure for synthesis of 3-amino-9H-carbazole (3) The suspension of 3-nitro-9H-carbazole (2, 119 mmol) and palladium on carbon (10%) in ethanol (150ml) was reacted with hydrogen gas at 35 psi for 3 hrs. The reaction mixture was filtered through a filter paper and the pad was washed 3 times with 60ml of methanol. The filtrate was evaporated under reduced pressure, and the residue was refined through acid-base extraction to gain the 3-amino-9H-carbazole.Yield 70.3 %, light brown solid, mp: 188.6 , Rf = 0.21 (1:1 n-hexane-ethyl acetate); 1H NMR (DMSO-d6, 400 MHz): δH 10.691(s, 1NH), 7.890(d, J=7.6Hz, 1H), 7.363-7.343(m, 1H), 7.270(ddd, J=1.2Hz, 7.2Hz, 7.2Hz, 1H), 7.230(d, J=2.4Hz, 1H), 7.183(dd, J=0.4Hz, 8.4Hz, 1H), 7.027(ddd, J=1.2Hz, 8Hz, 8Hz, 1H), 6.759(dd, J=2Hz, 8.4Hz, 1H), 4.665(s, NH2) |
66% | With sodium hydroxide; zinc In ethanol for 5h; Heating; | |
With methanol; nickel Hydrogenation; | ||
With hydrogenchloride; tin | ||
With potassium hydroxide; sodium dithionite | ||
With hydrogenchloride; zinc | ||
With potassium hydroxide; zinc | ||
With ethanol; platinum Hydrogenation; | ||
With hydrogenchloride; iron | ||
With potassium hydroxide; sodium dithionite | ||
With hydrogenchloride; ethanol; tin(ll) chloride | ||
With formic acid In acetonitrile at 20℃; Irradiation; | ||
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / Inert atmosphere 2: copper(II) choride dihydrate / dimethyl sulfoxide / 7 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium sulfide; ethanol | ||
With sodium sulfide | ||
With hydrogenchloride; tin |
Multi-step reaction with 2 steps 1: methanol. KOH-solution 2: Na2S2O4; methanol. KOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; sodium ethanolate at 300℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium hydroxide In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydrogencarbonate In tetrahydrofuran; water for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide In acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrazine hydrate In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 43% 2: 8% | With phosphorus trichloride In toluene for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid at 170℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid at 210℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With pyridine at 20℃; for 1h; 3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With dmap; 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With Montmorillonite K10 clay In methanol; dichloromethane at 20℃; | |
86% | In methanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In methanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With Montmorillonite K10 clay In methanol; dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / montmorillonite K10 clay / CH2Cl2; methanol / 20 °C 2: 73 percent / para-toluene sulfonic acid; montmorillonite K10 clay / 7 h / 60 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / montmorillonite K10 clay / CH2Cl2; methanol / 20 °C 2: 67 percent / para-toluene sulfonic acid; montmorillonite K10 clay / 6 h / 60 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / methanol / 1 h / Heating 2: 79 percent / bromine / acetic acid; acetonitrile / 0.5 h / 15 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 86 percent / methanol / 1 h / Heating 2: 80 percent / bromine / acetic acid; acetonitrile / 0.5 h / 15 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) acetic acid, Naac, 2) HCl / 1) H2O, ethanol, reflux, 3 h, 2) acetic acid, reflux, 0.5 h 2: 142 mg / chloranile / xylene / 6 h / Heating 3: 90 percent / N2H4*H2O / Raney-Ni / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 142 mg / chloranile / xylene / 6 h / Heating 2: 90 percent / N2H4*H2O / Raney-Ni / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / sodium hydrogencarbonate / tetrahydrofuran; H2O / 1 h / Heating 2: 59 percent / 0.5 h / 180 - 190 °C / Heating; in vacuo |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 95 percent / 0.5 h / Heating 2: 73 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h / Heating 3: 52 percent / pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / 0.5 h / Heating 2: 73 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / aq. KOH / acetone 2: 78 percent / lithium aluminium hydride / tetrahydrofuran / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 85 percent / aq. KOH / acetone 2: 78 percent / lithium aluminium hydride / tetrahydrofuran / 8 h / Heating 3: 83 percent / sodium acetate, sodium nitrite, acetic acid / H2O / 0.17 h / Ambient temperature 4: 73 percent / 100percent hydrazine hydrate / 10percent Pd/charcoal / ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / aq. KOH / acetone 2: 78 percent / lithium aluminium hydride / tetrahydrofuran / 8 h / Heating 3: 83 percent / sodium acetate, sodium nitrite, acetic acid / H2O / 0.17 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 0.33 h 2: NaCNBH3, AcOH / methanol / 48 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: glacial acetic acid; nitric acid; nitros gases / 55 - 60 °C 2: tin; diluted hydrochloric acid | ||
Multi-step reaction with 2 steps 1: glacial acetic acid / bei der Nitrierung 2: zinc dust; alcoholic KOH-solution | ||
Multi-step reaction with 2 steps 1: glacial acetic acid; nitric acid / 80 °C 2: Na2S2O4; alcoholic KOH-solution |
Multi-step reaction with 2 steps 1: glacial acetic acid; sodium nitrite; nitric acid 2: sodium sulfide | ||
Multi-step reaction with 2 steps 1: copper nitrate hemi(pentahydrate); acetic acid; acetic anhydride / 0.75 h / 60 °C 2: hydrazine hydrate; palladium 10% on activated carbon / tetrahydrofuran; ethanol; methanol / 1.08 h / 60 °C | ||
Multi-step reaction with 2 steps 1: nitric acid / water / 4 h / 20 - 80 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 1292.9 Torr | ||
Multi-step reaction with 2 steps 1: copper nitrate hemi(pentahydrate); acetic acid; acetic anhydride / 1 h / 20 - 100 °C 2: palladium 10% on activated carbon; hydrazine hydrate / ethanol / 24 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: nitric acid / water / 20 - 90 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 1810.07 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18 4-(4-[Amino(2-thienyl)methylidene]amino}phenyl)-N-(9H-carbazol-3-yl)butanamide Hydrochloride: Example 18 4-(4-[Amino(2-thienyl)methylidene]amino}phenyl)-N-(9H-carbazol-3-yl)butanamide Hydrochloride: 18 The experimental protocol used is the same as that described for Example 2, starting from 3-aminocarbazole (Pharmazie (1993) 48(11), 817-820) and 4-nitrophenylbutyric acid. Light beige solid. Melting point>250° C. MS: MH+: 452.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17 N'-(9H-Carbazol-3-yl)-2-thiophenecarboximidamide: Example 17 N'-(9H-Carbazol-3-yl)-2-thiophenecarboximidamide: 17 The experimental protocol used is the same as that described for Example 1, starting from 3-aminocarbazole (Pharmazie (1993) 48(11), 817-820). The product is isolated in the form of a free base. Light beige solid. Melting point: 243-244° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine | 4 EXAMPLE 4 EXAMPLE 4 115 g (1.05 mols) of p-hydroquinone, 180 g (0.99 mol) of 3-aminocarbazole, 30 ml of dimethyldiglycol (diglycol dimethyl ether) and 1 g of iodine are heated to 220° C. under nitrogen for 7 hours and a total of 50 ml (water of reaction+dimethyldiglycol) is distilled off over a small column. The yield of 3-(4-hydroxy-anilino)-carbazole is virtually quantitative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid In methanol | 7.b EXAMPLE 7 (b) The carbazoleazomethine required for the preparation of the above sulphur dyestuff, 3-(4-nitrobenzalamino)-carbazole, is prepared as follows A mixture of 1.5 l of ethylene glycol monoethyl ether, 300 g of 3-aminocarbazole, 250 g of p-nitrobenzaldehyde and 15 ml of formic acid is boiled under reflux for 4 hours, while stirring. The solvent is then driven off on a rotary evaporator, the residue is boiled up with 1 l of methanol and the suspension is filtered. The filter residue is rinsed with approx. 100 ml of methanol and is dried. Red crystals with a melting point of 198°-200° C.; yield 360 g (~70% of theory). The 9-ethyl derivative is obtained if 346 g of 3-amino-9-ethylcarbazole are reacted with p-nitrobenzaldehyde in accordance with the above instructions, intead of the 300 g of 3-aminocarbazole. The yield is 85% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With lanthanum(III) triflate In 1,4-dioxane at 150 - 160℃; for 12h; optical yield given as %de; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With indium(III) chloride; 1-ethyl-3-methylimidazolium tetrafluoroborate at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With oxygen; copper(I) bromide In dimethyl sulfoxide at 80℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 1 h / 80 °C 2: trichlorophosphate / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 1 h / 80 °C 2: trichlorophosphate / 1 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 6h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine In toluene for 24h; Inert atmosphere; Reflux; | 4.2 N′-(N-R-Carbazole-1)-2,3-bis(2,3,5-trimethylthienyl)maleimide (7-17) and N′-(N-R-carbazole-3)-2,3-bis(2,3,5-trimethylthienyl)-maleimide (18-27) General procedure: ‘One-pot’ reaction method was employed: N-R-1-nitrocarbazole or N-R-3-nitrocarbazole (1 mmol, 5a-k, 6a-j), 2,3-bis(2,3,5-trimethylthienyl)maleic anhydride (0.38 g, 1.1 mmol) were added to toluene (20 mL). Et3N (0.5 mL) was injected when the solution was heated to boiling point under N2 atmosphere, and the reaction was continued to reflux for 24 h. Cooled down, the solution was extracted with ethyl ether and distilled. Crude product was further purified by column chromatography (silica gel, eluent: hexane and ethyl acetate) and recrystallization with ethanol, giving light yellow crystal (or solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.4% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; | Procedure for the synthesis of (E)-(9H-carbazol-3-yl)-3-((methoxy)nphenyl)acrylamide (BS 1) To a solution of 3-methoxycinnamic acid (0.66 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 0.83 mmol) and 4-dimethylaminopyridine (4-DMAP, 0.22 mmol) in tetrahydrofuran anhydrous (20 mL) was added 9H-carbazol-3-amine (3, 0.55 mmol). The reaction mixture was stirred at room temperature for 24 h. The crude mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain BS 1. Yield 81.4 %, Ivory colored solid, mp: 246.0 , Rf = 0.60 (1:2 n-hexane-ethyl acetate); 1H NMR (400 MHz, DMSO-d6): δH 11.19 (s, NH), 10.13 (s, NH), 8.51 (s, 1H), 8.04 (d, J = 8.0 Hz, 1H), 7.58 (m, 4H), 7.46 (m, 2H), 7.37 (t, J = 7.6 Hz, 1H), 7.14 (t, J = 7.4 Hz, 1H), 7.02 (d, J = 8.8 Hz, 2H), 6.75 (d, J = 15.6 Hz, 1H), 3.80 (s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δC; 163.6, 160.6, 140.4, 139.2, 136.4, 131.3, 129.3, 127.5, 125.6, 122.4, 122.2, 120.2, 120.1, 118.9, 118.4, 114.5, 111.1, 111.0, 110.9, 55.2; IT-TOF/MS: m/z = 365.1190 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; | Procedure for the synthesis of (E)-N-(9H-carbazol-3-yl)-3-(3,4-dimethoxyphenyl)acrylamide (BS 2) To a solution of 3,4-dimethoxycinnamic acid (0.66 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 0.83 mmol) and 4-dimethylaminopyridine (4-DMAP, 0.22 mmol) in tetrahydrofuran anhydrous (20 mL) was added 9H-carbazol-3-amine (3, 0.55 mmol). The reaction mixture was stirred at room temperature for 24 h. The crude mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain BS 2. Yield 76.5%, Yellow colored solid, mp: 194.6 , Rf = 0.18 (1:1 n-hexane-ethyl acetate); 1H NMR(400MHz, DMSO-d6): δH 11.20 (s, NH), 10.14 (s, NH), 8.53 (s, 1H), 8.04 (d, J = 7.6 Hz, 1H), 7.60 (d, J = 8.8 Hz, 1H), 7.54 (d, J = 16.4 Hz, 1H), 7.46 (m, 2H), 7.38 (t, J = 7.4 Hz, 1H), 7.23 (s, 1H), 7.20 (d, J = 8.4 Hz, 1H), 7.15 (t, J = 7.4 Hz, 1H), 7.02 (d, J = 7.6 Hz, 1H), 6.77 (d, J = 15.2 Hz, 1H), 3.84 (s, 3H, OCH3), 3.80(s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δC; 163.6, 150.3, 149.0, 140.4, 139.6, 136.4, 131.3, 127.7, 125.7, 122.4, 122.2, 121.6, 120.4, 120.1, 118.8, 118.4, 111.8, 111.1, 111.0, 110.9, 110.0, 55.5, 55.4; IT-TOF/MS: m/z = 395.1314 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.2% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; | Procedure for the synthesis of (E)-N-(9H-carbazol-3-yl)-3-(3,4-dimethoxyphenyl)acrylamide (BS 3) To a solution of 3,4,5-trimethoxycinnamic acid (0.66 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC, 0.83 mmol) and 4-dimethylaminopyridine (4-DMAP, 0.22 mmol) in tetrahydrofuran anhydrous (20 mL) was added 9H-carbazol-3-amine (3, 0.55 mmol). The reaction mixture was stirred at room temperature for 24 h. The crude mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain BS 3. Yield 56.2 %, Yellow colored solid, mp: 204.0 , Rf = 0.31 (2:3 n-hexane-ethyl acetate); 1H NMR (400 MHz, DMSO-d6): δH 11.21 (s, NH), 10.20 (s, NH), 8.53 (s, 1H), 8.04 (d, J = 7.6 Hz, 1H), 7.60 (d, J = 8.8 Hz, 1H), 7.55 (d, J = 16.0 Hz, 1H), 7.46 (m, 2H), 7.38 (t, J = 7.6 Hz, 1H), 7.15 (t, J = 7.2 Hz, 1H), 6.98 (s, 2H), 6.84 (d, J = 15.6 Hz, 1H), 3.85 (s, 6H, OCH3 x 2), 3.71 (s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δC; 163.1, 153.1, 140.2, 139.5, 138.7, 136.3, 131.1, 130.5, 125.6, 122.3, 122.1, 122.0, 120.0, 118.7, 118.4, 111.0, 110.9, 110.7, 104.9, 56.2, 55.5 IT-TOF/MS: m/z = 425.1453 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.6% | In tetrahydrofuran at 25℃; for 24h; | 336 1- (9H-carbazol-3-yl) -3-phenylpropylurea To the anhydrous THF solution (10 ml) of 3-amino-9-methyl-9H-carbazole (1.098 mmol) was added the respective isocyanate compound (1.318 mmol) and the mixture was stirred at room temperature (25 ° C) for 24 hours. The stirred mixture was filtered, washed with ethyl acetate, and the powder on the filter paper was dissolved in acetone and subjected to column chromatography to obtain a pure compound |
80.6% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
In tetrahydrofuran at 20℃; for 24h; | 336 To the anhydrous THF solution (10 ml) of 3-amino-9-methyl-9H-carbazole (1.098 mmol) was added the respective isocyanate compound (1.318 mmol) and the mixture was stirred at room temperature (25 ° C) for 24 hours. The stirred mixture was filtered, washed with ethyl acetate, and the powder on the filter paper was dissolved in acetone and subjected to column chromatography to obtain a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: cesium fluoride / dimethyl sulfoxide / 24 h / 150 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 24 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: cesium fluoride / dimethyl sulfoxide / 24 h / 150 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 24 h / 110 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrazine hydrate / ethanol / 24 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With cesium fluoride In dimethyl sulfoxide at 150℃; for 24h; Inert atmosphere; | 6.3 (3) Synthesis of Intermediate N, N-bis (4-nitrophenyl) -9H-carbazol-3-amine The 1.822g (0.01mol) 9H-carbazol-3-amine and 5.305ml (0.05mol) difluoronitrobenzene was added to the flask 100ml three, DMSO as solvent, magnetically stirred and argon gas was heated to an oil bath at 150 , was added 3.038g (0.02mol), cesium fluoride (of CsF), the reaction was refluxed for 24h; the reaction mixture was poured into ice water, extracted with methylene chloride, the solvent was distilled off under reduced pressure, the product with dichloromethane: n-hexane = 1 : 1 (by volume) as the mobile phase, silica as the stationary phase for the column chromatography, the product was collected and spin dry, vacuum dried at 80 24h, to give the product 3.607g, 85% yield. This intermediate structure is as follows |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With iron(III)-acetylacetonate; hydrazine In butan-1-ol for 3h; Reflux; | 1 21 g of 3-azido carbazole,5 mL% 80% hydrate hydrazine,0.13 g catalyst Fe (acac) 3,50 mL of n-butanol into the reaction flask, heated to reflux 3h after the reaction is completed,Except that n-butanol,cool down,The mixture was added to 100 mL of ethyl acetate,Fully mixed,Filter,Removing part of the ethyl acetate solvent,The residue is recrystallized,To give 16 g of a white solid 3-aminocarbazole product (purity 97%, yield 89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1h; | 4.2.4. General procedure for the synthesis of LX2343 and A1-24 General procedure: To a stirred solution of 4 (355 mg, 1 mmol) and HATU (456 mg,1.2 mmol) in CH2Cl2 (6 mL) was added DIPEA (155 mg, 1.2 mmol)and the appropriate amine (1 mmol) at room temperature. Themixturewas continuously stirred for 1 h, and TLC indicated that thereaction was completed. Then the reaction mixture was concentratedand diluted with CH2Cl2 (10 mL) and H2O (10 mL). Theaqueous layer was separated and the organic layer was washedwith saturated Na2CO3 solution (2 10 mL), brine (10 mL) anddried over anhydrous Na2SO4. After filtered, the solvent wasevaporated to dryness under vacuum to obtain the desired crude products. The appropriate compounds (LX2343 and A1-24) wereobtained following purification by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(II) choride dihydrate In dimethyl sulfoxide at 100℃; for 7h; | General procedure for the synthesis of compounds (2a-2q), (7a-7d), (9, 11, 13) General procedure: A mixture of starting compound (2.69 mmol), CuCl2.2H2O (10 mol %) in DMSO (5 mL) stirred at 100 °C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.3% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.1% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.3% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.9% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.2% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.4% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.5% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.5% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.5% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.5% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.5% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.32% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | Procedure for synthesis of 4-nitrophenyl 9H-carbazole-3-ylcarbamate (12a-d, 12f, 12g) General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). The characterization data of 4-nitrophenyl 9H-carbazol-3-ylcarbamate (12a)Yield 85.32%, green gray solid, mp: 178.7 , Rf = 0.2(3:1 n-hexane-ethyl acetate); 1H NMR(DMSO-d6, 400MHz): δH 11.101(s, 1NH), 11.056(s, 1NH), 8.548(s, 1H), 8.277(s, 1H), 8.121(d, J=9Hz, 2H), 8.057(d, J=7.8Hz, 1H), 7.467-7.335(m, 3H), 7.130(dd, J=7.2Hz, 7.2Hz, 1H), 6.931(d, J=9Hz, 2H); 13C NMR(DMSO-d6, 100MHz) : δc 176.893, 167.466, 163.933, 140.282, 139.611, 135.662, 132.109, 131.704, 126.236, 125.446, 122.416, 120.076, 118.675, 118.201, 115.812, 110.975, 110.274. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.69% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | Procedure for synthesis of 4-nitrophenyl 9H-carbazole-3-ylcarbamate (12a-d, 12f, 12g) General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.32% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | Procedure for synthesis of 4-nitrophenyl 9H-carbazole-3-ylcarbamate (12a-d, 12f, 12g) General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.3% | With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3h; | General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.25% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | Procedure for synthesis of 4-nitrophenyl 9H-carbazole-3-ylcarbamate (12a-d, 12f, 12g) General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.71% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | Procedure for synthesis of 4-nitrophenyl 9H-carbazole-3-ylcarbamate (12a-d, 12f, 12g) General procedure: Substituted chloroformate was slowly added to a solution of 3-amino-9H-carbazole (3) and triethylamine in tetrahydrofuran anhydrous at 0. And the reaction mixture was stirred at room temperature for 3 hrs. Then, ethyl acetate and water were added. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel to get compounds (12a-d, 12f, 12g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.4% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.7% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). The characterization data of 1-(9H-carbazole-3-yl)-3-propylurea (5a)Yield 76.7%, gray solid, mp: 249 , Rf = 0.1 (1:1 n-hexane-ethyl acetate); 1H NMR (DMSO-d6, 400 MHz): δH 11.023(s, NH), 8.283(s, NH), 8.142(s,1H), 7.983(d, J=8.0Hz, 1H), 7.415(d, J=8.0Hz, 1H), 7.344-7.264(m, 3H), 7.092(t, J=7.6Hz, 1H), 6.066(t, J=5.6Hz, NH), 3.060(q, J=6.6Hz, 2H), 1.496-1.405(m, 2H), 0.881(t, J=7.4Hz, 3H); 13C NMR(DMSO-d6, 100MHz) : δc 155.836, 140.227, 135.329, 132.324, 125.318, 122.395, 122.329, 119.966, 118.369, 118.081, 110.902, 110.746, 109.741, 40.974, 23.158, 11.402; IT-TOF/MS: m/z 268.1418[M+H]+ . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.6% | In tetrahydrofuran at 20℃; | Procedure for synthesis of compounds (5a-p) General procedure: Substituted isocyanate was added to the solution of 3-amino-9H-carbazole (3, 0.549mmol) in tetrahydrofuran anhydrous. The reaction mixture was stirred at room temperature for 18-24 hrs. This mixture was added with ethyl acetate and water. The layer of ethyl acetate from this mixture was dehydrated by MgSO4, filtered and evaporated under reduced pressure. The residue was column chromatographed in silica gel using n-hexane/ethyl acetate (7:1) to get compounds (5a-p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(I) oxide; ammonium hydroxide; potassium carbonate at 140℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 2: hydrogenchloride / water; diethyl ether / 20 °C |
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 at 20℃; | (R tert Butyl (1-(isoindolin-2-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (7c). General procedure: A literature procedure1 was modified by replacing triethylamine with N,N-diisopropylethylamine. To a stirred mixture of tetrahydroisoindoline (0.11 mL, 1.0 mmol), N-Boc-(R)-phenylalanine (265 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (182 mg, 1.0 mmol) and anhydrous 1-hydroxybenzotriazole (203 mg, 1.5 mmol) in N,N-dimethylformamide (3.0 mL) was added N,N-diisopropylethylamine (1.3 mL, 7.5 mmol). The mixture was stirred at 20 for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 mL) and the solution was washed with water (2 x 20 mL). The combined aqueous fractions were re-extracted with ethyl acetate (2 x 20 mL) and all the combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2 x 20 mL) then with brine (20 mL) filtered and dried (MgSO4). Column chromatography (25:75 ethyl acetate: dichloromethane) of the residue gave 7c (175 mg, 48%) as a cream solid, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; Inert atmosphere; | 4 9H-carbazole-3-amine (23) 0.214 g (1.0 mmol) of compound 22, 0.52 g (2.0 mmol) of PPh3, and 12 mL of o-dichlorobenzene were added to a 50 mL round bottom flask, the system was replaced with N2 for 15 minutes, and then the temperature was raised to 180° C. for 24 hours. After the reaction is complete, cool to room temperature, evaporate and concentrate the solvent,Column separation and purification yielded 0.15 g of flake white crystal 23 with a yield of 81% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: 3-amino-9H-carbazole; 3-Phenoxybenzaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 4h; Stage #2: With trimethoxyboron sodium hydride In tetrahydrofuran; ethanol for 5h; | 4 N-(3-phenoxybenzyl)-9H-carbazole-3-amine (24) Add 0.182g (1.0mmol) of compound 23, 1.1mmol of m-phenoxybenzaldehyde, 0.43g (1.5mmol) of tetraisopropyl titanate (Ti(iOPr)4) and 0.1mL of THF into a 25mL round bottom flask, at room temperature After 4 hours of reaction, 20 mL of ethanol and 1.06 g (5.0 mmol) of NaBH(OAc) 3 were added to the system, and the reaction was continued for 5 hours. After the reaction is completed, 30 mL of ethanol and 2 mL of water are added to the reaction system under stirring to quench the excess tetraisopropyl titanate, filtered through Celite, the filtrate is spin-dried, and the final pure product 24 is obtained by column chromatography. Gray solid, yield: 92%. |
Tags: 6377-12-4 synthesis path| 6377-12-4 SDS| 6377-12-4 COA| 6377-12-4 purity| 6377-12-4 application| 6377-12-4 NMR| 6377-12-4 COA| 6377-12-4 structure
[ 161464-96-6 ]
1H-Indol-5-amine hydrochloride
Similarity: 0.96
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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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