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[ CAS No. 62581-82-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 62581-82-2
Chemical Structure| 62581-82-2
Chemical Structure| 62581-82-2
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Quality Control of [ 62581-82-2 ]

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Product Details of [ 62581-82-2 ]

CAS No. :62581-82-2 MDL No. :MFCD00045267
Formula : C10H11ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BNLRVFJSVGTTGG-UHFFFAOYSA-N
M.W : 198.65 Pubchem ID :2776723
Synonyms :

Calculated chemistry of [ 62581-82-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.89
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 2.03
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.695 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (Ali) : -2.15
Solubility : 1.41 mg/ml ; 0.00712 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.89
Solubility : 0.0258 mg/ml ; 0.00013 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 62581-82-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 62581-82-2 ]

* 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.

  • Downstream synthetic route of [ 62581-82-2 ]

[ 62581-82-2 ] Synthesis Path-Downstream   1~74

  • 1
  • [ 908094-01-9 ]
  • [ 24085-05-0 ]
  • [ 62581-82-2 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether
  • 2
  • [ 62581-82-2 ]
  • [ 143-33-9 ]
  • [ 403499-85-4 ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 3
  • [ 62581-82-2 ]
  • [ 531-99-7 ]
YieldReaction ConditionsOperation in experiment
With ethanol; hexamethylenetetramine
  • 4
  • [ 50-00-0 ]
  • [ 100-06-1 ]
  • [ 62581-82-2 ]
YieldReaction ConditionsOperation in experiment
97.4% With hydrogenchloride; water
With hydrogenchloride; water at 30 - 35℃;
With hydrogenchloride; water at 45℃;
With hydrogenchloride at 60℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
With hydrogenchloride for 10h; Heating; 5.1.1. General synthetic procedure of target compounds 5a-s General procedure: CS2 (2.3 mL, 30 mmol) was added dropwise to the mixture ofmethylamine derivative (30 mmol) and triethylamine (12 mL) inTHF (25 mL) at 0 C within 30 min. After stirring for 1 h at roomtemperature, the mixture was then cooled down to 0 C and thetoluene sulfonyl chloride (6 g, 31.5 mmol) were added in. Afterstirring for another 1 h at room temperature, the mixture wasdiluted with 5% HCl (100 mL) and petroleum ether, sequentiallywashed with water, saturated NaHCO3 solution and brine, driedwith anhydrous Na2SO4 and evaporated in vacuo to obtain compound1. HCl (10.5 mL) was added to the mixture of benzene orbenzene derivatives (6.65 mmol) and paraformaldehyde(11.97 mmol), and then stirred for 10 h at 60 C. After cooling downto room temperature, the mixture was then dispersed with waterand ethyl acetate, and sequentially washed with water, 5% HCl,saturated NaHCO3 solution and brine, dried with anhydrousNa2SO4. The solvent was then removed by evaporation to givecompound 2. Methyl 2-amino-4-hydroxybenzoate (0.01 mol) andisothiocyanate derivatives (0.01 mol) was heated in the presence oftriethylamine and ethanol at reflux temperature for 4 h. Aftercooling down to room temperature, the mixturewas filtered to giveintermediate 3, which was subsequently reacted with intermediate2 (0.01 mmol) in the presence of K2CO3 and 1,4-dioxane underreflux for 10 h. Then, the mixture was cooled down to room temperature,dissolved with ethyl acetate, sequentially washed withwater, 5% HCl, saturated NaHCO3 solution and brine, dried withanhydrous Na2SO4. Removal of the solvent gave a residue, whichwas then recrystallized in ethanol to obtain intermediate 4. Finally,the target compounds 5a-s were prepared by alkylating intermediate4 (5 mmol) with 2-dimethylaminoethyl chloride hydrochloride,2-diethylaminoethyl chloride hydrochloride or 3-dimethylaminopropyl chloride hydrochloride (6 mmol) in thepresence of 1, 4-dioxane and K2CO3, respectively. Spectra of thetarget compounds were shown in the Supplementary Material.
With hydrogenchloride In water at 60℃; for 10h;

  • 6
  • [ 2253-44-3 ]
  • [ 62581-82-2 ]
  • [ 107724-59-4 ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate In benzene Heating;
  • 7
  • [ 2253-52-3 ]
  • [ 62581-82-2 ]
  • [ 107699-95-6 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate In benzene Heating;
  • 8
  • [ 32650-55-8 ]
  • [ 62581-82-2 ]
  • [ 107699-96-7 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In benzene Heating;
  • 9
  • [ 62581-82-2 ]
  • [ 298-06-6 ]
  • [ 107699-92-3 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate In benzene Heating;
  • 10
  • [ 62581-82-2 ]
  • [ 756-80-9 ]
  • [ 7205-23-4 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In benzene for 3h; Heating;
  • 11
  • [ 38870-89-2 ]
  • [ 100-06-1 ]
  • [ 62581-82-2 ]
YieldReaction ConditionsOperation in experiment
99% With aluminium trichloride In nitromethane Friedel-Crafts conditions; other solvent: carbon disulphide;
  • 12
  • [ 62581-82-2 ]
  • [ 107-56-2 ]
  • [ 107699-94-5 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In benzene Heating;
  • 13
  • [ 62581-82-2 ]
  • [ 2253-43-2 ]
  • [ 107699-93-4 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In benzene Heating;
  • 14
  • [ 62581-82-2 ]
  • [ 451-13-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aqueous ethanol 3: HBr; acetic acid 4: peroxyacetic acid; acetic acid
  • 15
  • [ 62581-82-2 ]
  • [ 81860-95-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous ethanol 2: peroxyacetic acid; acetic acid
  • 16
  • [ 62581-82-2 ]
  • [ 90844-05-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aqueous ethanol 3: NaClO; aqueous NaOH
  • 17
  • [ 62581-82-2 ]
  • [ 81720-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aqueous ethanol 3: peroxyacetic acid; acetic acid
  • 18
  • [ 62581-82-2 ]
  • [ 81720-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aqueous ethanol 3: HBr; acetic acid
  • 19
  • [ 62581-82-2 ]
  • [ 116296-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous ethanol
  • 20
  • [ 62581-82-2 ]
  • (4-methoxy-<i>m</i>-phenylene)-di-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aqueous ethanol 3: sulfur / Behandeln des Reaktionsprodukts mit wss. Aethanol 4: acetic acid; aqueous H2SO4
  • 21
  • [ 62581-82-2 ]
  • [ 858453-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aqueous ethanol 3: sulfur / Behandeln des Reaktionsprodukts mit wss. Aethanol
  • 22
  • [ 99-93-4 ]
  • [ 62581-82-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; HCl 2: diethyl ether
  • 23
  • [ 62581-82-2 ]
  • [ 90536-48-4 ]
YieldReaction ConditionsOperation in experiment
66% With potassium hydroxide; calcium hypochlorite; potassium carbonate In 1,4-dioxane; water at 20 - 70℃; for 4.5h; H-00e Onto a warm solution of Ca(OCl)2 (7.14 g, 49.95 mmol, 3.3 eq.) in water (25 ml) isadded a warm solution of K2CO3 (5.14 g, 37.35 mmol, 2.49 eq.) and KOH (1.46 g, 26.1mmol, 1.74 eq.) in water (25 ml) . After 30 min of vigourous stirring, the undesiredsolid formed is filtered and rinsed with little water. The solution obtained is pouredonto a suspension of l-(3-chloromethyl-4-methoxy-phenyl)~ethanone (2.98 g, 15mmol) in 1,4-dioxane (10 ml). The resulting suspension is stirred 2 h at rt and 2 h at70°C.Under cooling of the suspension in an ice bath, are subsequently added solidNaHSOs (100 mg), then 96% sulfuric acid until pH = 3. The aqueous phase thusobtained is extracted four times with AcOEt. The combined organic phase is washedwith brine and dried over NaiSO^ Evaporation of the solvent in vacuo yields the titlecompound (1.8 g) in 66% as a white solid, fa = 0.72 min (LC-3), ESI-MS (pos.): m/z182.99 [M+Hf.
  • 24
  • [ 10273-89-9 ]
  • [ 62581-82-2 ]
  • [ 1192764-92-3 ]
YieldReaction ConditionsOperation in experiment
83% With 1-Adamantanecarboxylic acid; [RuCl2(p-cymene)]2; potassium carbonate In toluene at 100℃; for 20h; Inert atmosphere; regioselective reaction;
  • 25
  • [ 62581-82-2 ]
  • [ 43221-62-1 ]
  • [ 1192764-81-0 ]
YieldReaction ConditionsOperation in experiment
61% With 1-Adamantanecarboxylic acid; [RuCl2(p-cymene)]2; potassium carbonate In toluene at 100℃; for 20h; Inert atmosphere; regioselective reaction;
  • 26
  • [ 62581-82-2 ]
  • [ 75-98-9 ]
  • [ 1201798-94-8 ]
YieldReaction ConditionsOperation in experiment
87.5% With potassium carbonate 1.b b) 5-acetyl-2-methoxybenzyl pivalate Pivalic acid (868.4 mg, 8.51 mmol), potassium carbonate (1.2 g, 8.70 mmol) was dissolved in dimethylformamide, and 1-(3-(chloromethyl)-4-methoxyphenyl)ethanone(1.2 g, 6.06 mmol) obtained as above dissolved in 3 mL of dimethylformamide was added thereto under argon. The mixture was heated to 65° C. and reacted for 4 hours, added with water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography eluting with petroleum ether/ethyl acetate (V/V=8:1) to afford 1.4 g of the title compound as a yellow oil with a yield of 87.5%. MS(EI): 264. 1H NMR (400 MHz, CDCl3) δ 8.01-7.88 (m, 2H), 6.92 (d, J=9.1 Hz, 1H), 5.17 (s, 2H), 3.91 (s, 3H), 2.56 (s, 3H), 1.27 (s, 9H).
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 65℃; for 2h; Inert atmosphere; 1 Example 1; Pivalate Ester Route5-acetyl-2-methoxybenzyl pivalate (1) ;Pivalic acid (33.42 g, 327.2 mmol) was added to NMP (200 mL) and potassium carbonate (45.2 g, 327.2 mmol) at RT under an atmosphere of nitrogen. To the resulting suspension was added 1-[3-(chloromethyl)-4-methoxyphenyl]ethanone (50 g, 251.7 mmol) suspended in NMP (100 mL). Further NMP (50 mL) was added to the reaction vessel. The mixture was heated to 65° C. and held there for 120 minutes. Water (600 mL) was then added followed by toluene (400 mL). The resulting solution was allowed to settle and the upper organic layer retained. The lower aqueous layer was extracted with further toluene (200 mL) and the organic layers combined. The resulting organic layer was washed with water (250 mL) and concentrated in vacuo to afford a colourless oil (125 mL) containing the desired product (1) and toluene.NMR Spectrum: 1H NMR (400.132 MHz, DMSO-d6) δ 1.19 (9H, s), 2.52 (3H, s), 3.92 (3H, s) 5.12 (2H, s), 7.12-7.17 (1H, d), 7.88 (1H, d), 7.98 (1H, dd).
  • 27
  • [ 23012-14-8 ]
  • [ 62581-82-2 ]
  • [ 1309576-12-2 ]
  • 28
  • [ 62581-82-2 ]
  • [ 108-39-4 ]
  • [ 1152976-64-1 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; 5.1.1. General procedure for the synthesis of compounds 4a-c General procedure: A mixture of 2a-c (1.1 equiv), 3a-b (1 equiv) and K2CO3 (1.1 equiv) in DMF was stirred at 80 °C for 3 h. After cooling to room temperature, the mixture was diluted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc) to give the desired products 4a-c.
  • 29
  • [ 62581-82-2 ]
  • [ 106-48-9 ]
  • [ 1360060-03-2 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; 5.1.1. General procedure for the synthesis of compounds 4a-c General procedure: A mixture of 2a-c (1.1 equiv), 3a-b (1 equiv) and K2CO3 (1.1 equiv) in DMF was stirred at 80 °C for 3 h. After cooling to room temperature, the mixture was diluted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc) to give the desired products 4a-c.
  • 30
  • [ 877628-64-3 ]
  • [ 62581-82-2 ]
  • tert-butyl 2-{2-[(5-acetyl-2-methoxybenzyl)thio]-5-fluoro-1H-benzo[d]imidazol-1-yl}acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate In acetone for 0.5h; Inert atmosphere; Reflux; tert-Butyl 2-{2-[(5-acetyl-2-methoxybenzyl)thio]-5-fluoro-1H-benzo[d]imidazol-1-yl}acetate An orange suspension of tert-butyl 2-(5-fluoro-2-mercapto-1H-benzo[d]imidazol-1-yl)acetate (150 mg, 0.531 mmol), 1-[3-(chloromethyl)-4-methoxyphenyl]-1-ethanone (106 mg, 0.531 mmol, 1eq.) and K2CO3 (147 mg, 1.06 mmol, 2 eq.) in acetone (3 mL) is stirred at reflux for 30 min. After cooling, water (50 ml) is added and the resulting aqueous phase is extracted twice with CH2Cl2. The combined organic phase is washed with water, brine and evaporated in vacuo. The brown residue is purified by flash chromatography on 5g silica gel (eluent: gradient of heptane/AcOEt from 99:1 to 75:25). This yields 181 mg of the title compound as white foam (0.47 mmol, 76%).
  • 31
  • [ 877623-39-7 ]
  • [ 62581-82-2 ]
  • [ 877624-36-7 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; tert-Butyl 2-{2-[(5-acetyl-2-methoxybenzyl)thio]-1H-benzo[d]imidazol-1-yl}acetate An suspension of tert-butyl 2-(2-mercapto-1H-benzo[d]imidazol-1-yl)acetate (225 mg, 0.85 mmol), 1-[3-(chloromethyl)-4-methoxyphenyl]-1-ethanone (169 mg, 0.85 mmol, 1eq.) and K2CO3 (235 mg, 1.7 mmol, 2 eq.) in acetone (0.8 mL) is stirred at reflux for 1 h. The crude slurry is filtered over a sintered funnel and the solid rinsed with acetone. The combined organic phase is evaporated in vacuo. The residue is purified by flash chromatography on 5 g silica gel (eluent: gradient of heptane/AcOEt from 99:1 to 40:60). This yields 285 mg of the title compound as colorless gel which solidifies on standing (0.67 mmol, 79%).
  • 32
  • [ 877623-39-7 ]
  • [ 62581-82-2 ]
  • 2-{2-[(5-acetyl-2-methoxybenzyl)thio]-1H-benzo[d]imidazol-1-yl}acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
  • 33
  • [ 62581-82-2 ]
  • [ 1414663-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium iodide / acetonitrile / 1 h / Reflux; Inert atmosphere 1.2: 6 h / Reflux 2.1: bromine / chloroform / 40 °C / Darkness 3.1: potassium carbonate / acetonitrile / 0.75 h / 20 °C / Darkness
  • 34
  • [ 62581-82-2 ]
  • [ 1414663-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium iodide / acetonitrile / 1 h / Reflux; Inert atmosphere 1.2: 6 h / Reflux 2.1: bromine / chloroform / 40 °C / Darkness 3.1: potassium carbonate / acetonitrile / 0.75 h / 20 °C / Darkness 4.1: acetonitrile / 3 h / Photolysis
  • 35
  • [ 62581-82-2 ]
  • [ 1414663-10-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium iodide / acetonitrile / 1 h / Reflux; Inert atmosphere 1.2: 6 h / Reflux 2.1: bromine / chloroform / 40 °C / Darkness
  • 36
  • [ 62581-82-2 ]
  • Bis[N-2-(N',N''-trimethylacetyl)aminoethyl]amine [ No CAS ]
  • [ 1414663-09-4 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 1-[3-(chloromethyl)-4-methoxyphenyl]-1-ethanone With sodium iodide In acetonitrile for 1h; Reflux; Inert atmosphere; Stage #2: Bis[N-2-(N',N''-trimethylacetyl)aminoethyl]amine With potassium carbonate for 6h; Reflux;
  • 37
  • [ 100-06-1 ]
  • [ 62581-82-2 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; formaldehyd In water at 60℃; 1.a a)
1-(3-(chloromethyl)-4-methoxyphenyl)ethanone To p-methoxyacetophenone (1.0 g, 6.65 mmol), paraformaldehyde (362 mg, 11.97 mmol) and concentrated hydrochloric acid (10.5 mL) were added, and stirred overnight under 60° C. The reaction mixture was then cooled to room temperature, poured onto crushed ice, extracted with ethyl acetate, washed successively with water, saturated sodium bicarbonate aqueous solution, brine, dried over anhydrous sodium sulfate, and distilled off the organic solvent under reduced pressure to give 1.2 g of the title compound as a gray solid with a yield of 92%. 1H NMR (400 MHz, CDCl3): δ 8.03-7.91 (m, 2H), 6.94 (dd, J=8.6, 2.0 Hz, 1H), 4.67 (s, 2H), 3.95 (s, 3H), 2.57 (s, 3H).
  • 38
  • [ 62581-82-2 ]
  • [ 1201798-95-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate 2: 6 h / 54 °C
  • 39
  • [ 62581-82-2 ]
  • [ 1201798-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate 2.1: 6 h / 54 °C 3.1: acetic acid / water / 99 °C 3.2: 3 h / 99 °C
  • 40
  • [ 62581-82-2 ]
  • [ 1201798-97-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate 2.1: 6 h / 54 °C 3.1: acetic acid / water / 99 °C 3.2: 3 h / 99 °C 4.1: methoxybenzene; N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 20 - 80 °C
  • 41
  • [ 62581-82-2 ]
  • 5-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-chloropyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzyl pivalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate 2.1: 6 h / 54 °C 3.1: acetic acid / water / 99 °C 3.2: 3 h / 99 °C 4.1: methoxybenzene; N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 20 - 80 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C 5.2: 20 °C
  • 42
  • [ 62581-82-2 ]
  • 5-(2,4-di(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzyl pivalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate 2.1: 6 h / 54 °C 3.1: acetic acid / water / 99 °C 3.2: 3 h / 99 °C 4.1: methoxybenzene; N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 20 - 80 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C 5.2: 20 °C 6.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1.33 h / 160 °C / Microwave irradiation
  • 43
  • [ 62581-82-2 ]
  • (5-(2,4-bis(3-oxa-8-azabicyclo[3.2.1]octane-8-yl)pyrido[2,3-d]pyrimidin-7-yl)2-methoxy phenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate 2.1: 6 h / 54 °C 3.1: acetic acid / water / 99 °C 3.2: 3 h / 99 °C 4.1: methoxybenzene; N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 20 - 80 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C 5.2: 20 °C 6.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1.33 h / 160 °C / Microwave irradiation 7.1: potassium hydroxide / tetrahydrofuran; methanol / 20 °C
  • 44
  • [ 62581-82-2 ]
  • [ 91759-68-1 ]
  • 3-(5-acetyl-2-methoxybenzylsulfanyl)-5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.3% With potassium hydroxide Reflux; 5-(4-Alkoxyphenyl)-3-(R-sulfanyl)-4-phenyl-4H-1,2,4-triazoles (2h-2o). General procedure: 10 mmol of ethylene chlorohydrin [or chloroacetamide, 3-bromo-4-methoxybenzylchloride, 2-methoxy-5-acetylbenzyl chloride, 2-(2-chlorophenoxy)ethyl chloride] was added to a solution of 10 mmol of KOH and 10 mmol of triazole-3-thiol 1a-1d in 40 mL of EtOH (MeOH). The mixture was refluxed during 45-60 min and then cooled to ambient; 60 mL of water was added. The formed solid was filtered off, washed with water, and recrystallized from ethanol.
  • 45
  • C18H19N3OS [ No CAS ]
  • [ 62581-82-2 ]
  • 3-(5-acetyl-2-methoxybenzylsulfanyl)-5-(4-butoxyphenyl)-4-phenyl-4H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide Reflux; 5-(4-Alkoxyphenyl)-3-(R-sulfanyl)-4-phenyl-4H-1,2,4-triazoles (2h-2o). General procedure: 10 mmol of ethylene chlorohydrin [or chloroacetamide, 3-bromo-4-methoxybenzylchloride, 2-methoxy-5-acetylbenzyl chloride, 2-(2-chlorophenoxy)ethyl chloride] was added to a solution of 10 mmol of KOH and 10 mmol of triazole-3-thiol 1a-1d in 40 mL of EtOH (MeOH). The mixture was refluxed during 45-60 min and then cooled to ambient; 60 mL of water was added. The formed solid was filtered off, washed with water, and recrystallized from ethanol.
  • 46
  • [ 62581-82-2 ]
  • 6-iodo-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-iodo-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
  • 47
  • [ 62581-82-2 ]
  • 6-methyl-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-methyl-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
  • 48
  • [ 62581-82-2 ]
  • 6-hydroxy-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-hydroxy-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
With potassium carbonate In 1,4-dioxane for 4h; Reflux; 10 2-((5-acetyl-2-methoxybenzyl) thio) -3- (thiophene-2-methylene) -6- (2- (dimethylamino) ethoxy) quinazoline -4 (3H) -one (I10) In a similar manner as in Example 1,2-thio-3- (thiophene-2-methylene) -6-hydroxy-2,3-dihydroquinazolin-4 (1H) -one (0.44 g, 1.5 mmol)And anhydrous potassium carbonate (1.24g, 9mmol)Dissolved in 1.4-dioxane (1.5mL),Add 5-acetyl-2-methoxybenzyl chloride (0.3g, 1.5mmol) and reflux for 4h,Add 5mL of water to stop the reaction,Recover the solvent under reduced pressure,Get compound2-((5-acetyl-2-methoxybenzyl) thio) -3- (thiophene-2-methylene) -6-hydroxy-quinazolin-4 (3H) -one,
With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1. General synthetic procedure of target compounds 5a-s General procedure: CS2 (2.3 mL, 30 mmol) was added dropwise to the mixture ofmethylamine derivative (30 mmol) and triethylamine (12 mL) inTHF (25 mL) at 0 C within 30 min. After stirring for 1 h at roomtemperature, the mixture was then cooled down to 0 C and thetoluene sulfonyl chloride (6 g, 31.5 mmol) were added in. Afterstirring for another 1 h at room temperature, the mixture wasdiluted with 5% HCl (100 mL) and petroleum ether, sequentiallywashed with water, saturated NaHCO3 solution and brine, driedwith anhydrous Na2SO4 and evaporated in vacuo to obtain compound1. HCl (10.5 mL) was added to the mixture of benzene orbenzene derivatives (6.65 mmol) and paraformaldehyde(11.97 mmol), and then stirred for 10 h at 60 C. After cooling downto room temperature, the mixture was then dispersed with waterand ethyl acetate, and sequentially washed with water, 5% HCl,saturated NaHCO3 solution and brine, dried with anhydrousNa2SO4. The solvent was then removed by evaporation to givecompound 2. Methyl 2-amino-4-hydroxybenzoate (0.01 mol) andisothiocyanate derivatives (0.01 mol) was heated in the presence oftriethylamine and ethanol at reflux temperature for 4 h. Aftercooling down to room temperature, the mixturewas filtered to giveintermediate 3, which was subsequently reacted with intermediate2 (0.01 mmol) in the presence of K2CO3 and 1,4-dioxane underreflux for 10 h. Then, the mixture was cooled down to room temperature,dissolved with ethyl acetate, sequentially washed withwater, 5% HCl, saturated NaHCO3 solution and brine, dried withanhydrous Na2SO4. Removal of the solvent gave a residue, whichwas then recrystallized in ethanol to obtain intermediate 4. Finally,the target compounds 5a-s were prepared by alkylating intermediate4 (5 mmol) with 2-dimethylaminoethyl chloride hydrochloride,2-diethylaminoethyl chloride hydrochloride or 3-dimethylaminopropyl chloride hydrochloride (6 mmol) in thepresence of 1, 4-dioxane and K2CO3, respectively. Spectra of thetarget compounds were shown in the Supplementary Material.
  • 49
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-(2-(dimethylamino)ethoxy)-3-((thiophene-2-yl)methyl)quinazoline-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane
  • 50
  • [ 62581-82-2 ]
  • 6-fluoro-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-fluoro-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With potassium carbonate In 1,4-dioxane for 10h; Reflux; 1 2-((5-acetyl-2-methoxybenzyl)thio)-6-fluoro-3-(thiophene-2-methylene)quinazolin-4(3H)-one(I1) a mixture of methyl 2-amino-5-fluorobenzoate (1.69 g, 10 mmol) and 2-(isothiocyanate)thiophene (1.84 g, 12 mmol) and triethylamine (2 mL) in ethanol (50 mL) Heat to reflux for 4 hours.After cooling, the reaction mixture was suction filtered.Drying gave the compound 6-fluoro-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one. 6-Fluoro-3-(thien-2-ylmethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (0.44 g, 1.5 mmol) and anhydrous potassium carbonate (1.24 g, 9 mmol) in a mixture of 1.4-dioxane (1.5 mL),Add 3-(chloromethyl)-4-methoxyacetophenone(0.3 g, 1.5 mmol) was refluxed for 10 hours, quenched by adding 5 mL of water, and solvent was evaporated under reduced pressure.The obtained residue was dissolved in CH22Cl2 Recrystallization from ethanol gave the title compound (0.16 g, 17%).
17% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively. 5.1.1.1 2-((5-Acetyl-2-methoxybenzyl)thio)-6-fluoro-3-(thiophen-2-ylmethyl)quinazolin-4(3H)-one (4a) As a yellow powder, yield: 17%; m.p.158.3-162.8°C. Analytical data for 4a: 1H NMR (400MHz, CDCl3) δ ppm: 8.24 (d, J=2.0Hz, 1H, Ar-H), 8.00 (s, 1H, Ar-H), 7.89 (dd, J=8.4Hz, 2.4Hz, 1H, Ar-H), 7.84 (dd, J=8.4, 3.2Hz, 1H, Ar-H), 7.68 (dd, J=8.8, 4.8Hz, 1H, Ar-H), 7.44 (m, 1H, Ar-H), 7.20 (m, 1H, Ar-H), 6.91 (m, 2H, Ar-H), 5.42 (s, 2H, CH2), 4.56 (s, 2H, CH2), 3.96 (s, 3H, CH3), 2.50 (s, 3H, CH3); 13C NMR (100MHz, CDCl3) δ ppm: 196.65, 162.64, 161.58, 155.27, 144.18, 136.98, 132.01, 130.48, 129.93, 128.87, 128.40, 126.47, 126.31, 125.07, 123.35, 123.11, 112.06, 111.83, 110.11, 56.01, 42.52, 31.56, 26.39; ESI-MS: m/z 454.9 [M+H]+.
  • 51
  • [ 62581-82-2 ]
  • 6-chloro-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-chloro-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
  • 52
  • [ 62581-82-2 ]
  • 6-bromo-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-bromo-3-((thiophene-2-yl)methyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1 General procedure for the synthesis of compounds 1-4 General procedure: CS2 (2.3mL, 30mmol) was added dropwise to the mixture of 2-thiophenemethylamine (30mmol) and triethylamine (12mL) in THF (25mL) at 0°C within 30min. After stirring at room temperature for 1h, the mixture was cooled down to 0°C and then add the toluene sulfonyl chloride (6g, 31.5mmol). After stirring at room temperature for 1h, the mixture was dispersed in 5% HCl (100mL) and petroleum ether, washed sequentially with water, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4 and evaporated in vacuo to give compound 1. HCl (10.5mL) was added to the mixture of benzene or benzene derivatives (6.65mmol) and paraformaldehyde (11.97mmol). After stirring at 60°C for 10h, the mixture was cooled down to room temperature and then the mixture was dispersed in water and ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue to afford compound 2. A solution of methyl anthranilate or methyl anthranilate derivatives (0.01mol) and 2-(isothiocyanatomethyl)thiophene (1.55g, 0.01mol) in the mixture of triethylamine and ethanol was heated at reflux temperature for 4h. The reaction mixture was cooled down to room temperature and then filtered to give intermediate 3, which was then reacted with compound 2 (0.01mmol) mentioned above in the presence of K2CO3 and 1,4-dioxane. After reflux for 10h, the mixture was cooled down to room temperature and dissolved in ethyl acetate, washed sequentially with water, 5% HCl, saturated NaHCO3 solution and brine, dried with anhydrous Na2SO4. Removal of the solvent gave a residue which was recrystallized from ethanol to obtain target compound 4, respectively.
  • 53
  • [ 62581-82-2 ]
  • C15H12N2O2S [ No CAS ]
  • C25H22N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,4-dioxane; water for 4h; Reflux; 55 2-((5-acetyl-2-methoxybenzyl) thio) -3- (benzyl) -6- (2- (dimethylamino) ethoxy) quinazoline-4 (3H)- Ketone (I55) In a similar manner to Example 40, 2-thio-3- (benzyl) -6-hydroxy-2,3-dihydroquinazolin-4 (1H) -one (0.43 g, 1.5 mmol) and Water potassium carbonate (1.24g, 9mmol) was dissolved in 1,4-dioxane (1.5mL), 5-acetyl-2-methoxybenzyl chloride (0.3g, 1.5mmol) was added and refluxed for 4h, and 5mL was added. The reaction was terminated with water, and the solvent was recovered under reduced pressure to obtain compound 2-((5-acetyl-2-methoxybenzyl) thio) -3- (benzyl) -6-hydroxyquinazoline-4 (3H)- ketone,
With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1. General synthetic procedure of target compounds 5a-s General procedure: CS2 (2.3 mL, 30 mmol) was added dropwise to the mixture ofmethylamine derivative (30 mmol) and triethylamine (12 mL) inTHF (25 mL) at 0 C within 30 min. After stirring for 1 h at roomtemperature, the mixture was then cooled down to 0 C and thetoluene sulfonyl chloride (6 g, 31.5 mmol) were added in. Afterstirring for another 1 h at room temperature, the mixture wasdiluted with 5% HCl (100 mL) and petroleum ether, sequentiallywashed with water, saturated NaHCO3 solution and brine, driedwith anhydrous Na2SO4 and evaporated in vacuo to obtain compound1. HCl (10.5 mL) was added to the mixture of benzene orbenzene derivatives (6.65 mmol) and paraformaldehyde(11.97 mmol), and then stirred for 10 h at 60 C. After cooling downto room temperature, the mixture was then dispersed with waterand ethyl acetate, and sequentially washed with water, 5% HCl,saturated NaHCO3 solution and brine, dried with anhydrousNa2SO4. The solvent was then removed by evaporation to givecompound 2. Methyl 2-amino-4-hydroxybenzoate (0.01 mol) andisothiocyanate derivatives (0.01 mol) was heated in the presence oftriethylamine and ethanol at reflux temperature for 4 h. Aftercooling down to room temperature, the mixturewas filtered to giveintermediate 3, which was subsequently reacted with intermediate2 (0.01 mmol) in the presence of K2CO3 and 1,4-dioxane underreflux for 10 h. Then, the mixture was cooled down to room temperature,dissolved with ethyl acetate, sequentially washed withwater, 5% HCl, saturated NaHCO3 solution and brine, dried withanhydrous Na2SO4. Removal of the solvent gave a residue, whichwas then recrystallized in ethanol to obtain intermediate 4. Finally,the target compounds 5a-s were prepared by alkylating intermediate4 (5 mmol) with 2-dimethylaminoethyl chloride hydrochloride,2-diethylaminoethyl chloride hydrochloride or 3-dimethylaminopropyl chloride hydrochloride (6 mmol) in thepresence of 1, 4-dioxane and K2CO3, respectively. Spectra of thetarget compounds were shown in the Supplementary Material.
  • 54
  • [ 62581-82-2 ]
  • C15H18N2O2S [ No CAS ]
  • C25H28N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,4-dioxane for 4h; Reflux; 25 2-((5-acetyl-2-methoxybenzyl) thio) -3- (cyclohexylmethyl) -6- (2- (dimethylamino) ethoxy) quinazoline-4 ( 3H) -one (I25) In a similar manner to Example 20, 2-thio-3- (cyclohexylmethyl) -6-hydroxy-2,3-dihydroquinazolin-4 (1H) -one (0.44 g, 1.5 mmol) And anhydrous potassium carbonate (1.24g, 9mmol) were dissolved in 1,4-dioxane (30mL), 5-acetyl-2-methoxybenzyl chloride (0.3g, 1.5mmol) was added and refluxed for 4h, then added The reaction was terminated with 5 mL of water, and the solvent was recovered under reduced pressure to obtain compound 2-((5-acetyl-2-methoxybenzyl) thio) -3- (cyclohexylmethyl) -6-hydroxyquinazoline-4 (3H) -one,
With potassium carbonate In 1,4-dioxane for 10h; Reflux;
  • 55
  • [ 62581-82-2 ]
  • C13H10N2O3S [ No CAS ]
  • C23H20N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,4-dioxane; water for 4h; Reflux; 40 2-((5-acetyl-2-methoxybenzyl) thio) -6- (2- (dimethylamino) ethoxy) -3- (furan-2-methylene) quinazoline -4 (3H) -one (I40) In a similar manner to Example 30, 2-thio-3- (furan-2-methylene) -6-hydroxy-2,3-dihydroquinazolin-4 (1H) -one (0.41 g, 1.5 mmol) and anhydrous potassium carbonate (1.24 g, 9 mmol) in a solution of 1,4-dioxane (1.5 mL) and mixed with 5-acetyl-2-methoxybenzyl chloride (0.3 g, 1.5 mmol) under reflux for 4 h, 5 mL of water was added to terminate the reaction, and the solvent was recovered under reduced pressure to obtain compound 2-((5-acetyl-2-methoxybenzyl) thio) -3- (furan-2-methylene) -6-hydroxyquinazoline-4 (3H) -one,
With potassium carbonate In 1,4-dioxane at 90℃; for 10h; 5.1.1. General synthetic procedure of target compounds 5a-s General procedure: CS2 (2.3 mL, 30 mmol) was added dropwise to the mixture ofmethylamine derivative (30 mmol) and triethylamine (12 mL) inTHF (25 mL) at 0 C within 30 min. After stirring for 1 h at roomtemperature, the mixture was then cooled down to 0 C and thetoluene sulfonyl chloride (6 g, 31.5 mmol) were added in. Afterstirring for another 1 h at room temperature, the mixture wasdiluted with 5% HCl (100 mL) and petroleum ether, sequentiallywashed with water, saturated NaHCO3 solution and brine, driedwith anhydrous Na2SO4 and evaporated in vacuo to obtain compound1. HCl (10.5 mL) was added to the mixture of benzene orbenzene derivatives (6.65 mmol) and paraformaldehyde(11.97 mmol), and then stirred for 10 h at 60 C. After cooling downto room temperature, the mixture was then dispersed with waterand ethyl acetate, and sequentially washed with water, 5% HCl,saturated NaHCO3 solution and brine, dried with anhydrousNa2SO4. The solvent was then removed by evaporation to givecompound 2. Methyl 2-amino-4-hydroxybenzoate (0.01 mol) andisothiocyanate derivatives (0.01 mol) was heated in the presence oftriethylamine and ethanol at reflux temperature for 4 h. Aftercooling down to room temperature, the mixturewas filtered to giveintermediate 3, which was subsequently reacted with intermediate2 (0.01 mmol) in the presence of K2CO3 and 1,4-dioxane underreflux for 10 h. Then, the mixture was cooled down to room temperature,dissolved with ethyl acetate, sequentially washed withwater, 5% HCl, saturated NaHCO3 solution and brine, dried withanhydrous Na2SO4. Removal of the solvent gave a residue, whichwas then recrystallized in ethanol to obtain intermediate 4. Finally,the target compounds 5a-s were prepared by alkylating intermediate4 (5 mmol) with 2-dimethylaminoethyl chloride hydrochloride,2-diethylaminoethyl chloride hydrochloride or 3-dimethylaminopropyl chloride hydrochloride (6 mmol) in thepresence of 1, 4-dioxane and K2CO3, respectively. Spectra of thetarget compounds were shown in the Supplementary Material.
With potassium carbonate In 1,4-dioxane for 10h; Reflux;
  • 56
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-3-benzyl-6-(2-(dimethylamino)ethoxy)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 57
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-3-benzyl-6-(2-(diethylamino)ethoxy)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 58
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-(2-(dimethylamino)ethoxy)-3-(furan-2-ylmethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 59
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-(2-(diethylamino)ethoxy)-3-(furan-2-ylmethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 60
  • [ 62581-82-2 ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-(3-(dimethylamino)propoxy)-3-(furan-2-ylmethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 61
  • [ 62581-82-2 ]
  • 6-hydroxy-3-(thiophen-2-ylmethyl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-one [ No CAS ]
  • 2-((5-acetyl-2-methoxybenzyl)thio)-6-(3-(dimethylamino)propoxy)-3-(thiophen-2-ylmethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / 90 °C 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 62
  • [ 62581-82-2 ]
  • C26H25ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane
  • 63
  • [ 62581-82-2 ]
  • C28H33ClN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane
  • 64
  • [ 62581-82-2 ]
  • C30H33N3O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 65
  • [ 62581-82-2 ]
  • C30H34N4O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 66
  • [ 62581-82-2 ]
  • C31H36N4O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 67
  • [ 62581-82-2 ]
  • C31H35N3O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 68
  • [ 62581-82-2 ]
  • C32H41N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 69
  • [ 62581-82-2 ]
  • C32H42N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 70
  • [ 62581-82-2 ]
  • C33H44N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 71
  • [ 62581-82-2 ]
  • C32H42N4O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane 3: potassium carbonate / N,N-dimethyl-formamide
  • 72
  • [ 62581-82-2 ]
  • C29H37N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 73
  • [ 62581-82-2 ]
  • C30H39N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane / 90 °C
  • 74
  • [ 62581-82-2 ]
  • C31H41N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 10 h / Reflux 2: potassium carbonate / 1,4-dioxane / 90 °C
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