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CAS No. : | 1459-48-9 | MDL No. : | MFCD00193829 |
Formula : | C16H21N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JMBDVVUBXKXCIU-UHFFFAOYSA-N |
M.W : | 227.34 | Pubchem ID : | 598544 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 72.62 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.23 cm/s |
Log Po/w (iLOGP) : | 2.58 |
Log Po/w (XLOGP3) : | 4.87 |
Log Po/w (WLOGP) : | 3.74 |
Log Po/w (MLOGP) : | 3.98 |
Log Po/w (SILICOS-IT) : | 3.47 |
Consensus Log Po/w : | 3.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.51 |
Solubility : | 0.00698 mg/ml ; 0.0000307 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.15 |
Solubility : | 0.0016 mg/ml ; 0.00000706 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.11 |
Solubility : | 0.0176 mg/ml ; 0.0000774 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.67 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
77% | With hydrogenchloride; iron In methanol Reflux; | |
With hydrogen In ethyl acetate | ||
With hydrogen In ethanol |
With hydrogen | ||
With hydrogen In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) aq. NaNO2, aq. H2SO4, AcOH, (ii) aq. NaBr, CuSO4, Cu, H2SO4; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; | General procedure: Compound1a,b (0.15 mol), the specifi ed acetanilide (2a-d) (0.21 mol), andTFA (0.9 mol) were charged into a fl at-bottom fl ask equippedwith a refl ux condenser and electromagnetic stirrer (the reactantmolar ratio 1a,b : 2a-d : TFA = 1 : 1.4 : 6). The reaction mixturewas stirred for 3 h at 80 C. After completion of the reaction, TFAwas distilled off , the residue was hydrolyzed with 10% hydrochloricacid and fi ltered. A 20% sodium hydroxide solution wasadded to the fi ltrate with cooling (up to highly alkaline medium).The precipitate was collected on a fi lter and dried in vacuo. 4-(Tricyclo[3.3.1.13,7]dec-1-yl)aniline (3a). Yield 96%, maincomponent content 99%, m.p. 105-106 C. IR, ν/cm-1: 3360(NH2), 2896, 2846, 2646 (CH), 1685 (NH2), 1620 (C-CAr),1451 (CH2), 1305, 1282 (C-N), 1256, 1183, 1005, 965, 881,742, 674. MS (EI, 70 eV), m/z (Irel (%)): 228 [M + 1]+ (33.4),227 []+ (100), 185 [ - C3H6(Ad)] (1.2), 184 (5.4), 170[ - C3H6(Ad) - CH3] (75), 168 [ - C3H6(Ad) - CH3 - 2 H](1.2), 133 (disubstituted Ad) (10.6), 130 (2.4), 119 (1.2), 106(6.2), 91 (4), 77 (4.0). 1H NMR (300 MHz, CCl4, δ): 1.74 (s, 6 H,H(δ)); 1.87 (s, 6 H, H(β)); 2.04 (s, 3 H, H(γ)); 3.68 (s, 2 H,NH2); 6.44 (s, 2 H, H(2), H(6)); 7.18 (s, 2 H, H(3), H(5)). | |
5 g | Add HCl (1mol/L) solution to the reaction solution, After 40 hours of refluxing reaction, a white solid precipitated. Post-treatment: After cooling the reaction solution to 60C, Slowly add NaOH particles to the reaction solution, Exothermic heat is obvious, a lot of bubbles are formed, After no more bubbles were generated, a large amount of deionized water was added to the reaction solution to remove excess NaOH, and the organic phase was extracted with DCM, dried with anhydrous MgSO4 and filtered and concentrated. After passing through a silica gel column with DCM: n-hexane=1:5 as the eluent, and recrystallizing from n-hexane, intermediate 216-1, 5 g of white product is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene at 15℃; other temperatures; ΔS(excit.), ΔH(excit.); | ||
With triethylamine In toluene at 15℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene at 15℃; other temperatures; ΔS(excit.), ΔH(excit.); | ||
With triethylamine In toluene at 15℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene at 15℃; other temperatures; ΔS(excit.), ΔH(excit.); | ||
With triethylamine In toluene at 15℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With aniline; aluminium anilide In various solvent(s) at 175℃; for 9h; Further byproducts given; | |
51.2% | With aniline; aluminium anilide at 175℃; for 9h; Further byproducts given; | |
1: 23% 2: 51.3% 3: 10.1% 4: 1% | With aniline; aluminium anilide at 200℃; for 9h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 51.3% 3: 1% 4: 10.1% 5: 8.1% 6: 6.5% | With aniline; aluminium anilide at 200℃; for 9h; var. solvents, temp., and time, also aniline hydrochloride as catalyst; other N-metylated anilines; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aniline; aluminium anilide at 250℃; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 51.3% 3: 8.1% 4: 10.1% | With aniline; aluminium anilide at 200℃; for 9h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 51.3% 3: 10.1% 4: 6.5% | With aniline; aluminium anilide at 200℃; for 9h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; for 12h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In toluene at 15℃; other temperatures; ΔS(excit.), ΔH(excit.); | ||
With triethylamine In toluene at 15℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NaNO2, aq. H2SO4, AcOH, (ii) CuCl, aq. HCl; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.9% | With zinc(II) chloride at 195 - 225℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
die freie Base ist wenig haltbar; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. HNO3, aq. H2SO4 2: H2 / Ni / methanol / 15200 Torr | ||
Multi-step reaction with 2 steps 1: HNO3, CF3CO2H 2: H2 / Pd-C | ||
Multi-step reaction with 2 steps 1: acetic anhydride; nitric acid; sulfuric acid / -15 - -5 °C 2: hydrogenchloride; iron / methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O 3: aq. H2SO4 4: LiAlH4 / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O 3: aq. H2SO4 4: LiAlH4 / diethyl ether 5: aq. HBr / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O 3: aq. H2SO4 4: LiAlH4 / diethyl ether 5: aq. HBr / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O 3: aq. H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: (i) aq. NaNO2, H2SO4, (ii) /BRN= 3587243/, CuCN 2: KOH / methanol; H2O 3: aq. H2SO4 4: LiAlH4 / diethyl ether 5: aq. HBr / benzene 6: Mg / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 145 °C 2: aq. HCl | ||
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 48 h / Inert atmosphere 2.1: hydrogenchloride / methanol; water-d2 / 40 h / Reflux 2.2: 60 °C | ||
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 20 °C / Inert atmosphere 2: acetic anhydride; nitric acid; sulfuric acid / -15 - -5 °C 3: hydrogenchloride; iron / methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 145 °C 2: aq. HCl | ||
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 48 h / Inert atmosphere 2.1: hydrogenchloride / methanol; water-d2 / 40 h / Reflux 2.2: 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrogenchloride; sodium hydroxide; aniline In nitrogen; water | 3 EXAMPLE 3 EXAMPLE 3 14.0 parts of aniline, 15.3 parts of 36% w/w hydrochloric acid, 10.2 parts of zinc chloride and 11.4 parts of 1-adamantanol are sealed into a glass tube and placed in a rocking autoclave pressurised to 20 atmospheres with nitrogen. After rocking at 175° C. for 33 hours, the reaction product, after decomposition with 50 parts of sodium hydroxide in 100 parts of water, yields 13.3 parts of 4-(1-adamantyl)aniline mb0.7 174°-6° C. (78% yield). Crystallisation from ethanol gives colourless plates m.p. 106°-8° C. (literature 105° C.) with the following percentage composition by weight: |
Multi-step reaction with 5 steps 1: trifluoroacetic acid / 12 h / 20 °C 2: potassium permanganate; pyridine / water / 25 - 100 °C 3: sodium azide / water; acetone 4: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 5: hydrogenchloride / water | ||
Multi-step reaction with 6 steps 1: trifluoroacetic acid / 12 h / 20 °C 2: potassium permanganate; pyridine / water / 25 - 100 °C 3: thionyl chloride / water / Reflux 4: sodium azide / water; acetone 5: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 6: hydrogenchloride / water |
Multi-step reaction with 7 steps 1.1: trifluoroacetic acid / 12 h / 20 °C 2.1: potassium permanganate; pyridine / water / 25 - 100 °C 2.2: Reflux 2.3: Reflux 3.1: sodium hydroxide / water; ethanol / Reflux 4.1: thionyl chloride / water / Reflux 5.1: sodium azide / water; acetone 6.1: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 7.1: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine In dichloromethane at 0 - 20℃; for 12h; | Ethyl {(adamantan-1-yl)methyl]amino}oxoacetate (11a) General procedure: A solution of 400 mg (2.91 mmol) of ethyl chloroxoacetate in 1 mL of methylene chloride was added to a cold (0 °C) solution of 500 mg (3.03 mmol) of [(adamantan-1-yl)methyl]amine and 920 mg (9.09 mmol) of triethylamine in 10 mL of methylene chloride. The reaction mixture was stirred for 12 h at room temperature, after which the product was extracted with 50 mL of ether, and the ether extract was washed with 30 mL of 1N HCl and two 50-mL portions of distilled water, dried over Na2SO4, and evaporated to dryness. The remaining solid material was dried in a vacuum. |
With potassium carbonate In tetrahydrofuran at 0 - 20℃; | 106.iii (iii) Ethyl [4-(adamantan-1-yl)phenyl]amino}(oxo)acetate 5 mL of THF was added to 400 mg (1.76 mmol) of 4-(adamantan-1-yl)aniline, after which 292 mg (2.11 mmol) of potassium carbonate was added. 291 mg (1.94 mmol) of ethyl chloroglyoxylate was added at 0° C., and the mixture was stirred at room temperature for 2 hours. Thereafter, the mixture was filtered using silica gel, and the filtrate was condensed. The obtained crude product was then separated and purified by silica gel column chromatography, thereby quantitatively giving ethyl [4-(adamantan-1-yl)phenyl]amino}(oxo)acetate. 1H-NMR (CDCl3) δ: 1.43 (3H, t, J=7.2 Hz), 1.64-2.18 (15H, m), 4.42 (2H, q, J=7.2 Hz), 7.32-7.41 (2H, m), 7.53-7.62 (2H, m), 8.85 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; diphenylphosphoranyl azide / tetrahydrofuran / 0 - 80 °C 2: hydrogenchloride / ethyl acetate / 10 h / 0 - 20 °C | ||
Multi-step reaction with 4 steps 1: thionyl chloride / water / Reflux 2: sodium azide / water; acetone 3: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 4: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tert-butyl [4-(adamantan-1-yl)phenyl]carbamate With hydrogenchloride In ethyl acetate at 0 - 20℃; for 10h; Stage #2: With sodium hydrogencarbonate In water | 106.ii (ii) 4-(Adamantan-1-yl)aniline 4 mL of ethyl acetate was added to 678 mg (2.07 mmol) of tert-butyl [4-(adamantan-1-yl)phenyl]carbamate, and then 4 mL of 4N hydrogen chloride/ethyl acetate was added at 0° C. The mixture was stirred at room temperature for 10 hours. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue. The resultant was washed with an aqueous sodium hydrogen carbonate solution and saturated saline in this order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, thereby quantitatively giving 4-(adamantan-1-yl)aniline. 1H-NMR (CDCl3) δ: 1.60-2.17 (15H, m), 3.46 (2H, brs), 6.61-6.71 (2H, m), 7.11-7.21 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane Reflux; | 5.1.1. General procedure for synthesis of N-cycloalkyl-(cycloalkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides (4.1-4.10) General procedure: Method A. The thionyl chloride (1.2 g, 0.011 mol) was added to the solution of proper acid (3.1-3.4) (0.01 mol) in 10 mL of anhydrous dioxane with subsequent adding of the 2-3 drops of DMF. Mixture was heated at the water bath at 60-80° till full elimination of hydrochloric acid. Then proper amine (0.01 mol) was added to the resulting mixture with stirring and refluxing for 2-3 h. The mixture was poured in the water, neutralized to pH 6-7 by acetic acid. The precipitate was filtered, dried and recrystallized from dioxane-water (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane Reflux; | 5.1.1. General procedure for synthesis of N-cycloalkyl-(cycloalkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides (4.1-4.10) General procedure: Method A. The thionyl chloride (1.2 g, 0.011 mol) was added to the solution of proper acid (3.1-3.4) (0.01 mol) in 10 mL of anhydrous dioxane with subsequent adding of the 2-3 drops of DMF. Mixture was heated at the water bath at 60-80° till full elimination of hydrochloric acid. Then proper amine (0.01 mol) was added to the resulting mixture with stirring and refluxing for 2-3 h. The mixture was poured in the water, neutralized to pH 6-7 by acetic acid. The precipitate was filtered, dried and recrystallized from dioxane-water (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reflux; | 5.1.1. General procedure for synthesis of N-cycloalkyl-(cycloalkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides (4.1-4.10) General procedure: Method B. N,N'-carbonyldiimidazole (1.95 g, 0.011 mol) was added to a solution of proper acid (3.1-3.4) (0.01 mol) in 10 mL of anhydrous dioxane or DMF and heated at the water bath at 60-80°C for 1 h with calcium chloride tube. The proper amine (0.01 mol) was added with stirring to the resulting mixture and refluxed for 2-3 h. The mixture was poured in the water, neutralized to pH 6-7 by acetic acid. The precipitate was filtered, dried and recrystallized from the dioxane-water (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reflux; | 5.1.1. General procedure for synthesis of N-cycloalkyl-(cycloalkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides (4.1-4.10) General procedure: Method B. N,N'-carbonyldiimidazole (1.95 g, 0.011 mol) was added to a solution of proper acid (3.1-3.4) (0.01 mol) in 10 mL of anhydrous dioxane or DMF and heated at the water bath at 60-80°C for 1 h with calcium chloride tube. The proper amine (0.01 mol) was added with stirring to the resulting mixture and refluxed for 2-3 h. The mixture was poured in the water, neutralized to pH 6-7 by acetic acid. The precipitate was filtered, dried and recrystallized from the dioxane-water (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reflux; | 5.1.1. General procedure for synthesis of N-cycloalkyl-(cycloalkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides (4.1-4.10) General procedure: Method B. N,N'-carbonyldiimidazole (1.95 g, 0.011 mol) was added to a solution of proper acid (3.1-3.4) (0.01 mol) in 10 mL of anhydrous dioxane or DMF and heated at the water bath at 60-80°C for 1 h with calcium chloride tube. The proper amine (0.01 mol) was added with stirring to the resulting mixture and refluxed for 2-3 h. The mixture was poured in the water, neutralized to pH 6-7 by acetic acid. The precipitate was filtered, dried and recrystallized from the dioxane-water (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: 1-Adamantyl bromide With zinc In tetrahydrofuran for 2h; Reflux; Stage #2: p-aminoiodobenzene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran Inert atmosphere; Reflux; | Representative Procedures General procedure: Preparation of 1-adamantylzinc bromide (A): In an oven-dried 250 mL round-bottomed flask equipped with a stir bar was added 6.54 g of active zinc (Zn*,100.0 mmol) in 100 mL of THF. Next, 1-bromoadamantane (10.5 g, 50.0 mmol) was cannulated into the flask at room temperature. The resulting mixture was then allowed to reflux for 2 h. The solution was cooled to room temperature and settled down. Then the supernatant was used for the subsequent coupling reactions. Preparation of adamantan-1-yl-(4-methoxyphenyl)methanone (1c): Into a 25 mL round-bottomed flask were placed CuCN (0.02 g, 10 mol %) and LiCl (0.02 g, 20 mol %). The flask was pumped down and recharged with argon gas. Then, 2.0 mL of THF was added to dissolve. The flask was cooled to 0 °C using an ice-bath. 4-Methoxybenzoyl chloride (0.24 g, 1.4 mmol) dissolved in 2.0 mL of THF was added into the flask. Next, 4.0 mL of 1-adamantylzinc bromide (0.5M in THF, 2.0 mmol) was cannulated into the flask under argon atmosphere at 0 °C, then the whole mixture was allowed to warm up gradually to room temperature over 3 h while being stirred. Quenched with saturated 3M HCl solution, then extracted with ethyl ether (10 mL × 3). Washed with saturated NaHCO3, 8% NH4OH solutions, and brine, then dried over anhydrous MgSO4. Purification by flash column chromatography (hexanes/ethyl acetate) afforded 0.16 g of 1c in 42% isolated yield as a pale yellow solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium permanganate; pyridine / water / 25 - 100 °C 2: sodium azide / water; acetone 3: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 4: hydrogenchloride / water | ||
Multi-step reaction with 5 steps 1: potassium permanganate; pyridine / water / 25 - 100 °C 2: thionyl chloride / water / Reflux 3: sodium azide / water; acetone 4: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 5: hydrogenchloride / water | ||
Multi-step reaction with 6 steps 1.1: potassium permanganate; pyridine / water / 25 - 100 °C 1.2: Reflux 1.3: Reflux 2.1: sodium hydroxide / water; ethanol / Reflux 3.1: thionyl chloride / water / Reflux 4.1: sodium azide / water; acetone 5.1: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 6.1: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium hydroxide / water; ethanol / Reflux 2: thionyl chloride / water / Reflux 3: sodium azide / water; acetone 4: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 5: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium azide / water; acetone 2: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 3: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With bis-(2-chloroethyl)amine hydrochloride at 150℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydrogencarbonate In water at 80℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: trifluoroacetic acid / 12 h / 20 °C 2: potassium permanganate; pyridine / water / 25 - 100 °C 3: sodium azide / water; acetone 4: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 5: hydrogenchloride / water | ||
Multi-step reaction with 6 steps 1: trifluoroacetic acid / 12 h / 20 °C 2: potassium permanganate; pyridine / water / 25 - 100 °C 3: thionyl chloride / water / Reflux 4: sodium azide / water; acetone 5: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 6: hydrogenchloride / water | ||
Multi-step reaction with 7 steps 1.1: trifluoroacetic acid / 12 h / 20 °C 2.1: potassium permanganate; pyridine / water / 25 - 100 °C 2.2: Reflux 2.3: Reflux 3.1: sodium hydroxide / water; ethanol / Reflux 4.1: thionyl chloride / water / Reflux 5.1: sodium azide / water; acetone 6.1: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 105 - 130 °C 7.1: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h; | General Procedure for the synthesis of thioureas. General procedure: To the 1 equiv. of corresponding amine in 30 equiv. of DMF was added 1 equiv. of 1-isothiocyanatoadamantane and 1 equiv. (2 equiv. in case of amine hydrochloride) of Et3N at room temperature. The reaction mass was heated at 80 °C for 12 h. After cooling down to room temperature 0.5N HCl and water was added and the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h; | General Procedure for the synthesis of thioureas. General procedure: To the 1 equiv. of corresponding amine in 30 equiv. of DMF was added 1 equiv. of 1-isothiocyanatoadamantane and 1 equiv. (2 equiv. in case of amine hydrochloride) of Et3N at room temperature. The reaction mass was heated at 80 °C for 12 h. After cooling down to room temperature 0.5N HCl and water was added and the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 8h; | 5 General procedure for the synthesis of ureas 3a-j General procedure: To 1 equiv. of corresponding amine 2a-j in 40 equiv. of DMF was added 1 equiv. of 2-fluorophenyl isocyanate and 1 equiv. of Et3N (2 equiv. when amine used in form of hydrochloride) at 0°C. The reaction mixture was stirred at room temperature overnight. After adding 1N HCl and water, the resulting white precipitates were collected by suction filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 4-(tricyclo[3.3.1.13,7]dec-1-yl)aniline; toluene-4-sulfonic acid With acetic acid In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: With tert.-butylnitrite In tetrahydrofuran at 0 - 20℃; for 1.16667h; | Diazonium Tosylates 4a-k; General Procedure General procedure: To a stirred ice-cooled solution/suspension of the corresponding aniline(15.0 mmol) in THF (5 mL), a solution of p-toluenesulfonic acidmonohydrate (3.043 mg, 16.0 mmol) in glacial acetic acid (15 mL) wasadded. The resulting suspension was stirred for 5 min and t-BuONO(2.44 mL, 22.5 mmol) was added in one portion. The mixture wasstirred at 0 °C for 20 min, then the ice bath was removed and stirringwas continued for 50 min at ambient temperature. The resulting solutionwas poured into Et2O (150 mL) and the mixture was stirred for 30min. The precipitate was collected by filtration, washed with Et2O(2 × 50 mL) and dried under reduced pressure at 30 °C. The obtainedarenediazonium tosylates were used without any further purification. |
Stage #1: 4-(tricyclo[3.3.1.13,7]dec-1-yl)aniline; toluene-4-sulfonic acid With acetic acid In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: With tert.-butylnitrite In tetrahydrofuran at 0 - 20℃; for 1.16667h; | 3-Arylglutaconic acids 1a - p General procedure: To a stirred ice-cooled solution or suspension of the respective aniline (15.0 mmol) in THF (5 mL) was added a solution of p-TsOH·H2O (3.04 g, 16.0 mmol) in glacial AcOH (15 mL). The resulting suspension was stirred for 5 min whereupon t-BuONO (2.44 mL, 22.5 mmol) was added in one portion. The mixture was stirred at 0 °C for 20 min, the ice bath was removed, and the stirring was continued for 50 min at r.t. The resulting solution was poured into Et2O (150 mL) and the mixture was stirred for 30 min. The precipitate of 9 (crystalline in all cases ex- cept for 9d) was separated, washed with Et2O, and dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid / tetrahydrofuran / 0.08 h / 0 °C 1.2: 1.17 h / 0 - 20 °C 2.1: palladium diacetate / methanol / 15 h / 20 °C 3.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid / tetrahydrofuran / 0.08 h / 0 °C 1.2: 1.17 h / 0 - 20 °C 2.1: palladium diacetate / methanol / 15 h / 20 °C 3.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 20 °C 4.1: toluene / 16 h / Reflux; Dean-Stark |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid / tetrahydrofuran / 0.08 h / 0 °C 1.2: 1.17 h / 0 - 20 °C 2.1: palladium diacetate / methanol / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] In dichloromethane at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In dichloromethane at 20℃; for 20.5h; | N1,N2-Bis(adamantan-1-yl)oxamide (12a) General procedure: A solution of 210 mg (1 mmol) of oxalyl chloride in 5 mL of methylene chloride was added dropwise to a solution of 500 mg (2 mmol ) of (adamantan-1-yl)amine in 5 mL of methylene chloride at room temperature over the course of 30 min. The reaction mixture was stirred for 20 h at room temperature, after which the product was filtered off and dried in a vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 3 h / 80 °C 2: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid / tetrahydrofuran / 0.08 h / Cooling with ice 1.2: 1.17 h / 0 - 20 °C 2.1: silver nitrate; 1,4-diaza-bicyclo[2.2.2]octane / tetrahydrofuran; N,N-dimethyl-formamide / 0.08 h / 0 °C 2.2: 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With triethylamine In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With triethylamine In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In methanol; water at 100℃; for 8h; | Step-c: Synthesis of 4-((3r,5r,7r)-adamantan-1-yl)-2-chloroaniline (Intermediate-I) General procedure: To a solution of N-(4-((3r,5r,7r)-adamantan-1-yl)-2-chlorophenyl)acetamide (17 g, 56 mmol, 1.0 eq.) in methanol (150 mL), cone. HCl (150 mL) was added and refluxed at 100 °C for 8h. Excess methanol was removed in vacuo. The white ppt. obtained was filtered off. The filtered solid was washed with a solution of Sodium bicarbonate followed by water and dried under vacuum. Desired product was obtained as a white solid (13 g, 88%). 1H NMR (400 MHz, DMSO-d6) d 7.08 (d, 7=2.4 Hz, 1H), 7.02 (dd, Ji=l.9 Hz, 72= 8.3 Hz, 1H), 6.73 (d, ,7=8.3 Hz, 1H), 5.09 (bs, 2H), 2.01 (s, 3H), 1.76 (s, 6H), 1.66 (s, 6H); LC-MS: m/z 262.2 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-(tricyclo[3.3.1.13,7]dec-1-yl)aniline; C14H10BrF3N2O2 With sodium t-butanolate In toluene for 0.0833333h; Schlenk technique; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0) In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; | General procedure: To an oven-dried Schlenk tube was added amine (1 mmol) and bromide (1 mmol) and toluene (3 mL). To the above homogeneous solution t-BuONa (1.5 mmol) was added. After stirring for 5 minutes, Pd2(dba)3(0.05 mmol) and Bu3P (0.075 mmol), were added under nitrogen atmosphere. The mixture was stirred for 24 h at 110 °C. After cooling to r.t., the reaction mixture was diluted with ethyl acetate (50 mL) and filtered through bed of diatomaceous earth. The organic solution was dried with MgSO4, concentrated in vacuo and purified by flash column chromatography with hexane/ethyl acetate (gradient of pure hexane to 10/1 hexane/ethyl acetate) as eluent to give desired product. Yield 50-54% For Compound 3f 1H NMR (500 MHz, CDCl3): d 9.45 (s, 1H), 8.01(s, 1H), 7.49-7.33. (d, 2H), 7.23-7.01 (m, 5H), 6.91-7.04 (d, 2H), 6.94 (s, 1H), 3.93 (s, 3H), 5.99 (s, 1H) 2.21-1.98 (m, 15H) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; | Step-a: Synthesis of methyl 2-(4-bromobenzamido)benzoate (Intermediate-IV) General procedure: A solution of methyl 2-aminobenzoate (5 g, 33.1 mmol, 1.0 eq.) in DCM (50 mL) was added with triethylamine (11 g, 108 mmol, 3 eq.) followed by 4-bromobenzoyl chloride (7.2 g, 33.1 mmol, 1.0 eq.) and stirred at RT overnight. Reaction mixture was extracted with ethyl acetate from water and concentrated in vacuo. The crude was washed with n-pentane and dried to afford title product (9 g, 85%). 1H NMR (400 MHz, DMSO-d6) d 11.52 (s, 1H), 8.47 (d, J= 8.3 Hz, 1H), 8.04 (d, J=8.4 Hz,1H), 7.89 (d, =8.8 Hz, 2H), 7.83 (d, J= 8.8 Hz, 2H), 7.67 (t, =7.3 Hz, 1H), 7.24 (t, J=1 Hz, 1H), 3.87 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; | Step-a: Synthesis of methyl 2-(4-bromobenzamido)benzoate (Intermediate-IV) General procedure: A solution of methyl 2-aminobenzoate (5 g, 33.1 mmol, 1.0 eq.) in DCM (50 mL) was added with triethylamine (11 g, 108 mmol, 3 eq.) followed by 4-bromobenzoyl chloride (7.2 g, 33.1 mmol, 1.0 eq.) and stirred at RT overnight. Reaction mixture was extracted with ethyl acetate from water and concentrated in vacuo. The crude was washed with n-pentane and dried to afford title product (9 g, 85%). 1H NMR (400 MHz, DMSO-d6) d 11.52 (s, 1H), 8.47 (d, J= 8.3 Hz, 1H), 8.04 (d, J=8.4 Hz,1H), 7.89 (d, =8.8 Hz, 2H), 7.83 (d, J= 8.8 Hz, 2H), 7.67 (t, =7.3 Hz, 1H), 7.24 (t, J=1 Hz, 1H), 3.87 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: triethylamine / tetrahydrofuran / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | 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 at 20℃; for 16h; Cooling with ice; | a Step-a: Synthesis of methyl 2-((4-((4-((3R,5S)-adamantan-1-yl )phenyl)carbamoyl)phenyl)amino)benzoate (Intermediate-XV) A solution of compound-XIV (0.2 g, 0.74 mmol, 1 eq.) and Intermediate-I.1 (0.185 g, 0.81 mmol, 1.1 eq.) was cooled in ice. HATU (0.34 g, 0.89 mmol, 1.2 eq.) followed by DIPEA (0.39 mL, 2.22 mmol, 3 eq.) were added and allowed to stir at RT for 16h. Reaction mass was added to ice water slowly under stirring. The obtained precipitate was filtered, washed with cold water twice followed by n-pentane twice and dried in vacuo to afford title compound as cream coloured solid (0.35 g, 98%). 1H NMR (400 MHz, DMSO-d6) d 10.01 (s, 1H), 9.43 (s, 1H), 7.96-7.91 (m, 3H), 7.69 (d, J=8.4 Hz, 2H), 7.54-7.49 (m, 1H), 7.45 (d, J= 8.0 Hz, 1H), 7.34-7.31 (m, 4H), 6.95 (t, J= 6.8 Hz, 1H), 3.86 (s, 3H), 2.06 (s, 3H), 1.87 (s, 6H), 1.74 (s, 6H); LC-MS: m/z 481.1 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-(tricyclo[3.3.1.13,7]dec-1-yl)aniline; methyl 2-[(3-bromophenyl)amino]benzoate With sodium t-butanolate In toluene for 0.0833333h; Schlenk technique; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0) In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; | General procedure: To an oven-dried Schlenk tube was added amine (1 mmol) and bromide (1 mmol) and toluene (3 mL). To the above homogeneous solution t-BuONa (1.5 mmol) was added. After stirring for 5 minutes, Pd2(dba)3(0.05 mmol) and Bu3P (0.075 mmol), were added under nitrogen atmosphere. The mixture was stirred for 24 h at 110 °C. After cooling to r.t., the reaction mixture was diluted with ethyl acetate (50 mL) and filtered through bed of diatomaceous earth. The organic solution was dried with MgSO4, concentrated in vacuo and purified by flash column chromatography with hexane/ethyl acetate (gradient of pure hexane to 10/1 hexane/ethyl acetate) as eluent to give desired product. Yield 42-55% For Compound 3a1H NMR (500 MHz, CDCl3): d 9.45 (s, 1H), 8.01(s, 1H), 7.5-7.7.30 (m, 2H), 7.2-7.1 (m, 2H), 6.98 (s, 1H), 6.8 (s, 1H) 6.78-6,26 (m, 4H), 5.99 (s, 1H) 3.90 (s, 3H),2.23-1.97 (m, 15H) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine In dichloromethane at 0 - 20℃; for 3h; | a Step-a: Synthesis of N-(4-(N-(4-((3r,5r,7r)-adamantan-1-yl) phenyl )sulfamoyl )phenyl )acetamide (Intermediate-XVI) A solution of Intermediate- 1 (0.5 g, 2.2 mmol) in dichloromethane (10 mL) was cooled to 0 °C and added with triethylamine (0.66 g, 6.6 mmol, 3 eq.) followed by 4-acetamidobenzenesulfonyl chloride (0.51 g, 2.2 mmol) and stirred at RT for 3h. Reaction mass was concentrated in vacuo and added with cold water. The obtained solid was filtered and dried under vacuum to afford title product (0.88 g, 94%). LC-MS: m/z 425.1 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine In dichloromethane at 20℃; for 2h; | a Step-a: Synthesis of phenyl (4-((3r,5r,7r)-adamantan-1-yl)phenyl)carbamate (XlXa) A solution of Intermediate-I.l (0.5 g, 2.2 mmol, 1 eq.) and phenyl chloroformate (0.42 g, 2.64 mmol, 1.2 eq.) in DCM was added with triethylamine (0.44 g, 4.4 mmol, 2 eq.) and stirred at RT for 2h. Reaction mixture was washed with water, concentrated in vacuo and purified by combi- flash to afford title compound as white solid (0.48 g, 63%). 1H NMR (400 MHz, DMSO-d6) d 10.10 (s, 1H), 7.44-7.39 (m, 4H), 7.31-7.19 (m, 5H), 2.05 (s, 3H), 1.84 (s, 6H), 1.73 (s, 6H); LC-MS: m/z 348.1 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tris-(dibenzylideneacetone)dipalladium(0); XPhos In toluene at 110℃; for 16h; Inert atmosphere; | a Step-a: Synthesis of methyl 2-((4-((4-((3R,5R)-adamantan-1-yl)phenyl )amino) phenyl) amino) benzoate (Intermediate-VI): A solution of Intermediate-II (0.5 g, 1.63 mmol, 1.0 eq.) and Intermediate- 1 (0.37 g, 1.63 mmol, 1.0 eq.) in toluene (10 mL) was de-gassed with N2 gas for 15 min. Pd2dba3(0.12 g, 0.13 mmol, 0.08 eq.) and XPhos (0.16 g, 0.326 mmol, 0.2 eq.) were added and de-gassed for 5 min. Reaction mass was heated at 110 °C for 16h. Reaction mass was filtered through celite, concentrated in vacuo and purified by combi-flash to afford the title product as pale yellow solid (0.26 g, 35%). 1H NMR (400 MHz, DMSO-d6) d 9.14 (s, 1H), 8.02 (s, 1H), 7.86 (dd, Ji=A Hz, 72=7.8 Hz, 1H), 7.35 (t, 7=1.4 Hz, 1H), 7.21 (d, 7=8.8 Hz, 2H), 7.12-6.96 (m, 7H), 6.69 (t, 7=6.8 Hz, 1H), 3.85 (s, 3H), 2.04 (s, 3H), 1.83 (s, 6H), 1.72 (s, 6H); LC-MS: m/z 452.4 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium cyanoborohydride / methanol / 0.25 h / 20 °C 2: toluene-4-sulfonic acid; sodium tetrahydroborate / methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium cyanoborohydride In methanol at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.5% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 108℃; for 3h; Inert atmosphere; | 2 Intermediate 216-1 (5g, 21.9mmol), intermediate A1 (6.4g, 21.9mmol), tris(dibenzylideneacetone) dipalladium (0.2g, 0.20mmol), 2-dicyclohexylphosphorus-2 ',6'-Dimethoxybiphenyl (0.4g, 0.2mmol) and sodium tert-butoxide (3.1g, 32.9mmol) were added to toluene (40mL), heated to 108 under nitrogen protection, stirred for 3h; then cooled At room temperature, the reaction solution was washed with water and dried with magnesium sulfate. After filtration, the filtrate was decompressed to remove the solvent; the crude product was purified by recrystallization using a toluene system to obtain a white solid intermediate 216-2 (6.1 g, yield 63.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 20 °C / Inert atmosphere 2: acetic anhydride; nitric acid; sulfuric acid / -15 - -5 °C 3: hydrogenchloride; iron / methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: Glyoxal; 4-(tricyclo[3.3.1.13,7]dec-1-yl)aniline In methanol at 20℃; for 19h; Stage #2: formaldehyd With ammonium chloride In methanol for 1h; Reflux; Stage #3: With phosphoric acid In methanol for 19h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium hydrogencarbonate In methanol for 16h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In ethanol for 26h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In ethanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 0.5 h / 20 °C 2: di-<i>tert</i>-butyl dicarbonate; dmap / ethanol / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: cesium fluoride / dimethyl sulfoxide / 15 h / 150 °C 2: hydrazine hydrate; palladium 10% on activated carbon / ethanol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride In dimethyl sulfoxide at 150℃; for 15h; | 2 Take 0.5 mol of p-adamantyl aniline and 1.1 mol of p-chloronitrobenzene,Dissolved in a three-necked bottle containing 500 ml of dimethyl sulfoxide with a thermometer and a magnetic rotor,After the dissolution is complete,Add 0.8mol of cesium fluoride,The temperature was raised to 150°C for 15h.After the reaction is complete,Pour the solution into water,Stir quickly, settle for 12h,Suction and wash several times,After drying, a yellow solid crude product was obtained.The crude dinitro compound was recrystallized using acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: cesium fluoride / dimethyl sulfoxide / 15 h / 120 °C 2: hydrazine hydrate; palladium 10% on activated carbon / ethanol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride In dimethyl sulfoxide at 120℃; for 15h; | 1 Take 0.1 mol of p-adamantyl aniline and 0.21 mol of p-fluoronitrobenzene,Dissolved in containing 100One milliliter of dimethyl sulfoxide in a three-necked bottle with a thermometer and a magnetic rotor,After the dissolution is complete,Add 0.16mol of cesium fluoride,The temperature was raised to 120°C for 15h.After the reaction is complete,Pour the solution into water,Stir quickly,Settling for 12h,Suction and wash several times,After drying, a yellow solid crude product was obtained.The crude dinitro compound was recrystallized using acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 85℃; for 8h; Inert atmosphere; | 1-7 Example 6: Under the protection of nitrogen, add 4-(1-adamantyl)aniline (100mmol, 22.7g), p-chlorobromobenzene (100mmol, 19.1g), sodium tert-butoxide (150mmol, 14.4 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1mmol, 0.74g), 1,1'-binaphthyl-2, 2' -bis-diphenylphosphine ( 4mmol, 2.49g), 300mL of toluene, heated to 85 degrees, the reaction was 8h, TLC monitored the completion of the reaction, cooled to room temperature, filtered to remove inorganic salts, the organic phase was concentrated to about 50ml of solvent, a large amount of solid precipitated, filtered to obtain intermediate M- 1 29.1g, yield 86%. |
Tags: 1459-48-9 synthesis path| 1459-48-9 SDS| 1459-48-9 COA| 1459-48-9 purity| 1459-48-9 application| 1459-48-9 NMR| 1459-48-9 COA| 1459-48-9 structure
[ 58788-79-7 ]
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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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