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[ CAS No. 83558-37-6 ] {[proInfo.proName]}

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Product Details of [ 83558-37-6 ]

CAS No. :83558-37-6 MDL No. :MFCD02663861
Formula : C10H10N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :NUMMWUVARLSQFR-UHFFFAOYSA-N
M.W :206.26 Pubchem ID :734629
Synonyms :

Calculated chemistry of [ 83558-37-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.45
TPSA : 76.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.41
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.216 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0684 mg/ml ; 0.000331 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.0535 mg/ml ; 0.000259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 83558-37-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83558-37-6 ]

* 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 [ 83558-37-6 ]

[ 83558-37-6 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 4755-77-5 ]
  • [ 83558-37-6 ]
  • [ 74604-51-6 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine In tetrahydrofuran for 3h; Ambient temperature;
  • 4
  • [ 5000-65-7 ]
  • [ 17356-08-0 ]
  • [ 83558-37-6 ]
YieldReaction ConditionsOperation in experiment
94.3% In ethanol at 20℃; 5.19 2-BROMO-1- (3-METHOXY-PHENYL)-ETHANONE (0.7291 g, 3.183 mmol) and thiourea (0.2665 g, 3.501 mmol) were dissolved in a 20 mL of ethanol. The reaction mixture was allowed to stir overnight at room temperature. The ethanol was evaporated to dryness and the crude product was dissolved in a minimum of dichloromethane. The crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness to yield the product (0. 619 g, 3.00 mmol, 94. 3 %). ESI-MS M/Z calc. 206.3, found 207.0 (M1) + Retention time 1.86 MINUTES. 1H NMR (400 MHz, CD3CN) 6 3.84 (s, 3H), 5.67 (s, 2H), 6.85- 6.91 (m, 2H), 7.31 (t, J = 7.9 Hz, 1H), 7.36-7. 43 (m, 2H).
90% In ethanol for 6h; Reflux;
With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL In acetonitrile at 20℃; for 0.25h;
In ethanol for 3h; Reflux;
In ethanol for 3h; Reflux; General procedure: (iii) A mixture of the above synthetic 9a-10n(calculate to yield 100% for last step, 4 mmol, 1.0 equiv.) and thiourea (4.4 mmol,1.1 equiv.) in anhydrous ethanol (50 mL) was refluxed for 3 h. After that, thesolvent was removed in vacuo andwashed with cold ether. Then the mixture was extracted dichloromethane (3*15mL) and washed with saturated aqueous NaHCO3. The combined organicphases were dried with anhydrous Na2SO4. Then removingthe solvent, the residue was purified by silica gel column (hexane/EtOAc=8:1 to4:1) and dried under vacuum to give 4-arylthiazol-2-amine 10a-10n, yieldwas 50~90%.
Reflux;
In ethanol for 1h; Reflux; Inert atmosphere; 31.i (i) 4-(3-Methoxyphenyl)thiazol-2-amine To a solution of 2-bromo-1 -(3-methoxyphenyl)ethan-1 -one (305 mg) in 8 mL dry EtOH was added thiourea (106 mg) in portions and heated to reflux for 1 h. After completion of the reaction as monitored by LCMS the solvent was removed under reduced pressure and a sat. solution of NaHC03 was added. The resulting solution was extracted three times with ethyl acetate and the combined organic phases were washed with brine, dried over Na2S04 and the solvents were removed under reduced pressure. The crude product was used without further purification. (0717) Yield: 232 mg MS (ES+) [M+H]+: m/e = 207.1 , RT: 0.897 min
In ethanol Reflux;

Reference: [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2005/26137, 2005, A2 Location in patent: Page/Page column 247-248
[2]Parvizi, Jafar; Mahmoodi, Nosrat O.; Ghanbari Pirbasti, Fateme [Journal of Sulfur Chemistry, 2018, vol. 39, # 2, p. 140 - 150]
[3]Habermann, Joerg; Levy, Steven V.; Scicinski, Jan J.; Scott, James S.; Smits, Rene; Thomas, Andrew W. [Journal of the Chemical Society. Perkin transactions I, 1999, # 17, p. 2425 - 2428]
[4]Luo, Yong; Zhu, Yongxia; Ran, Kai; Liu, Zhihao; Wang, Ningyu; Feng, Qiang; Zeng, Jun; Zhang, Lidan; He, Bing; Ye, Tinghong; Zhu, Shirui; Qiu, Xiaolong; Yu, Luoting [MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042]
[5]Ran, Kai; Gao, Chao; Deng, Hongxia; Lei, Qian; You, Xinyu; Wang, Ningyu; Shi, Yaojie; Liu, Zhihao; Wei, Wei; Peng, Cuiting; Xiong, Lu; Xiao, Kunjie; Yu, Luoting [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674]
[6]Gundala, Trivikram Reddy; Godugu, Kumar; Nallagondu, Chinna Gangi Reddy [Journal of the Chinese Chemical Society, 2017, vol. 64, # 12, p. 1408 - 1416]
[7]Current Patent Assignee: FORSCHUNGSVERBUND BERLIN EV - WO2019/234237, 2019, A1 Location in patent: Page/Page column 83; 103
[8]Nasli Esfahani, Anita; Iraji, Aida; Alamir, Amir; Moradi, Shahram; Asgari, Mohammad Sadegh; Hosseini, Samanesadat; Mojtabavi, Somayeh; Nasli-Esfahani, Ensieh; Faramarzi, Mohammad Ali; Bandarian, Fatemeh; Larijani, Bagher; Hamedifar, Haleh; Hajimiri, Mir Hamed; Mahdavi, Mohammad [Molecular Diversity, 2021]
  • 6
  • [ 333-20-0 ]
  • [ 5000-65-7 ]
  • [ 83558-37-6 ]
YieldReaction ConditionsOperation in experiment
60% With aluminum oxide; ammonium acetate; silica gel In benzene at 90℃; for 16h;
  • 7
  • [ 83558-37-6 ]
  • [ 75-36-5 ]
  • <i>N</i>-[4-(3-methoxy-phenyl)-thiazol-2-yl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.1% With pyridine In dichloromethane at 20℃; for 1h;
  • 8
  • [ 586-37-8 ]
  • [ 83558-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polymer-supported pyridinium bromide perbromide / toluene / 10 °C 2: polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 0.25 h / 20 °C
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide / acetonitrile / 20 °C 2: ethanol / 3 h / Reflux
Multi-step reaction with 2 steps 1: tetra-N-butylammonium tribromide / acetonitrile / 12 h / 20 °C 2: ethanol / 3 h / Reflux
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; N-Bromosuccinimide / acetonitrile / 2 h / Reflux 2: ethanol / Reflux

  • 9
  • [ 83558-37-6 ]
  • 2-pyrrolidinoacetamido-4-m-methoxyphenylthiazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / benzene / 3 h / Heating 2: 65 percent / K2CO3 / ethanol / 8 h / Heating 3: 60 percent / HCl (gas) / benzene
  • 10
  • [ 83558-37-6 ]
  • 2-piperidinoacetamido-4-m-methoxyphenylthiazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / benzene / 3 h / Heating 2: 75 percent / K2CO3 / ethanol / 8 h / Heating 3: 75 percent / HCl (gas) / benzene
  • 11
  • [ 83558-37-6 ]
  • 2-(N,N-diisobutylaminoacetamido)-4-m-methoxyphenylthiazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / benzene / 3 h / Heating 2: 70 percent / K2CO3 / ethanol / 8 h / Heating 3: 65 percent / HCl (gas) / benzene
  • 12
  • [ 83558-37-6 ]
  • 2-(N,N-dibenzylaminoacetamido)-4-m-methoxyphenylthiazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / benzene / 3 h / Heating 2: 72 percent / K2CO3 / ethanol / 8 h / Heating 3: 75 percent / HCl (gas) / benzene
  • 13
  • [ 83558-37-6 ]
  • [ 83558-24-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / benzene / 3 h / Heating 2: 65 percent / K2CO3 / ethanol / 8 h / Heating
  • 14
  • [ 83558-37-6 ]
  • [ 83558-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / benzene / 3 h / Heating 2: 75 percent / K2CO3 / ethanol / 8 h / Heating
  • 15
  • [ 83558-37-6 ]
  • [ 83558-21-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / benzene / 3 h / Heating 2: 70 percent / K2CO3 / ethanol / 8 h / Heating
  • 16
  • [ 83558-37-6 ]
  • [ 83558-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / benzene / 3 h / Heating 2: 72 percent / K2CO3 / ethanol / 8 h / Heating
YieldReaction ConditionsOperation in experiment
In ethanol for 2h; Reflux; Example 1 Synthesis of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4-phenylthiazol-2-yl)benzamide (ZA1) General procedure: Compound 1a and p-toluenesulfonic acid (TsOH, 0.1 eq)Dissolved in anhydrous dichloromethane,Stir at room temperature,N-Bromosuccinimide (NBS, 1.0 eq) was added in batches,Heating to reflux, after 12h, TLC detected that the reaction was complete,The reaction solution changed from pale yellow to reddish brown.After cooling to room temperature, add an appropriate amount of saturated salt water to wash the silk.Extracted with dichloromethane, dried over anhydrous sodium sulfate,The solvent was evaporated under reduced pressure, and the residue was separated by column chromatography to give a brown-red oil.Thiourea (1.2eq) was dissolved in ethanol, stirred at room temperature,An ethanol solution of brown-red oil was added and heated to reflux.After 2h, TLC detected that the reaction was complete, and the reaction solution changed from light yellow to dark yellow.After cooling, the solvent was evaporated under reduced pressure, and an appropriate amount of saturated sodium bicarbonate solution was added for washing.Extraction with ethyl acetate, drying over anhydrous sodium sulfate, evaporation of the solvent under reduced pressure,The residue was separated by column chromatography to give pale yellow solid 4a in 63% yield.
  • 18
  • [ 66377-37-5 ]
  • [ 83558-37-6 ]
  • (E)-N-(4-(3-methoxyphenyl)thiazol-2-yl)-3-(4-morpholinophenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: p-Morpholino-cinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Stage #2: 4-(3-methoxyphenyl)-2-aminothiazole In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
  • 19
  • [ 17954-81-3 ]
  • [ 83558-37-6 ]
  • 4-(3-(4-(3-methoxyphenyl)thiazol-2-ylamino)propoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.3% With potassium carbonate In N,N-dimethyl-formamide for 12h; Reflux; 4.1.1. 4-(3-(4-Phenylthiazol-2-ylamino)propoxy)benzaldehyde (3a) General procedure: To a solution of 4-(3-bromopropoxy)benzaldehyde (200.00 mg, 0.82 mmol)and 4-phenylthiazol-2-amine (144.50 mg, 0.82 mmol) in DMF (15 mL),potassium carbonate (170.00 mg, 1.23 mmol) was added. The reaction mixturewas refluxed for 12 h. The reaction mixture was quenched with water,and extracted with toluene (20 mL*3). The combined organic layer waswashed with brine, dried with anhydrous sodium sulphate, concentratedunder vacuum, then purified by flash chromatography (petroleum ether:ethyl acetate = 3:1) to afford a colorless solid. Yield 32.3%. The procedure described for the synthesis of compound 3a can also beapplied to the synthesis of compounds 3b-o.
  • 20
  • [ 17954-81-3 ]
  • [ 83558-37-6 ]
  • ethyl (E)-2-(4-(3-(4-(3-methoxyphenyl)thiazol-2-ylamino)propoxy)phenyl)ethenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere
  • 21
  • [ 83558-37-6 ]
  • 5-amino-N-(4-(3-methoxyphenyl)thiazol-2-yl)furan-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h / 20 °C 2: iron; ammonium chloride / ethanol; water / 6 h / Reflux
  • 22
  • [ 88-14-2 ]
  • [ 83558-37-6 ]
  • N-(4-(3-methoxyphenyl)thiazol-2-yl)furan-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; General procedure: (iv) 10a-10n (2 mmol, 1.0 equiv.) wasdissolved in dry dichloromethane (10 mL), and the reaction was followed to add 5-nitro-2-furoicacid (2.4 mmol, 1.2 equiv.), DMAP (2.4 mmol, 1.2 equiv.), EDCI (4 mmol, 2.0 equiv.),then stirred under room temperature for 1 day. The reaction mixture wasquenched with H2O (10 mL) and extracted with dichloromethane (2*30 mL).The combined organic layers were washed in turn with 2N HCl (20 mL), H2O(20 mL) and brine (20 mL). The organic layer was collected, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel (hexane/EtOAc=8:1 to 4:1) toprovide 12a-12n. 11a and 11b were prepared by thesame way, just starting from 10b and replacing 5-nitro- furic with2-furoic acid and 4-nitrobenzoic acid. The yield was 29~80%.
  • 23
  • [ 83558-37-6 ]
  • [ 62-23-7 ]
  • N-(4-(3-methoxyphenyl)thiazol-2-yl)-4-nitrobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.6% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; General procedure: (iv) 10a-10n (2 mmol, 1.0 equiv.) wasdissolved in dry dichloromethane (10 mL), and the reaction was followed to add 5-nitro-2-furoicacid (2.4 mmol, 1.2 equiv.), DMAP (2.4 mmol, 1.2 equiv.), EDCI (4 mmol, 2.0 equiv.),then stirred under room temperature for 1 day. The reaction mixture wasquenched with H2O (10 mL) and extracted with dichloromethane (2*30 mL).The combined organic layers were washed in turn with 2N HCl (20 mL), H2O(20 mL) and brine (20 mL). The organic layer was collected, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel (hexane/EtOAc=8:1 to 4:1) toprovide 12a-12n. 11a and 11b were prepared by thesame way, just starting from 10b and replacing 5-nitro- furic with2-furoic acid and 4-nitrobenzoic acid. The yield was 29~80%.
  • 24
  • [ 645-12-5 ]
  • [ 83558-37-6 ]
  • N-(4-(3-methoxyphenyl)thiazol-2-yl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.7% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; General procedure: (iv) 10a-10n (2 mmol, 1.0 equiv.) wasdissolved in dry dichloromethane (10 mL), and the reaction was followed to add 5-nitro-2-furoicacid (2.4 mmol, 1.2 equiv.), DMAP (2.4 mmol, 1.2 equiv.), EDCI (4 mmol, 2.0 equiv.),then stirred under room temperature for 1 day. The reaction mixture wasquenched with H2O (10 mL) and extracted with dichloromethane (2*30 mL).The combined organic layers were washed in turn with 2N HCl (20 mL), H2O(20 mL) and brine (20 mL). The organic layer was collected, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel (hexane/EtOAc=8:1 to 4:1) toprovide 12a-12n. 11a and 11b were prepared by thesame way, just starting from 10b and replacing 5-nitro- furic with2-furoic acid and 4-nitrobenzoic acid. The yield was 29~80%.
  • 25
  • [ 83558-37-6 ]
  • [ 129-64-6 ]
  • (3aR,4S,7R,7aS)-2-(4-(3-methoxyphenyl)thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In toluene for 36h; Reflux;
  • 26
  • bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic anhydride [ No CAS ]
  • [ 83558-37-6 ]
  • (4R,7S)-2-(4-(3-methoxyphenyl)thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 4-(3-methoxyphenyl)-2-aminothiazole With triethylamine In toluene for 0.166667h; Stage #2: bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic anhydride In toluene for 48h; Reflux; General procedure for synthesis of (4R,7S)-2-(4-phenylthiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives (9a-j) General procedure: Thiazole derivative (3a-h and 5a,b) (1 mmol) was dissolved in toluene (7.5 mL) and NEt3 (1 mL) and stirred forabout 10 min. Then, dicarboxylicanhydride (8) (1 mmol)in toluene (7.5 mL) was added drop wise into the reaction mixture. The reaction mixture was reuxed for 48 h.Toluene was removed by a rotovap. The residue wasextracted with chloroform, the organic layer was driedover Na2SO4 and solvent was removed by rotovap. Thecrude product was crystallized in chloroform/hexane (3/7)mixture.
  • 27
  • [ 78912-11-5 ]
  • [ 83558-37-6 ]
  • C25H23N9OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With base for 12h; Heating;
  • 28
  • [ 19847-10-0 ]
  • [ 83558-37-6 ]
  • N-(4-(3-methoxyphenyl)thiazol-2-yl)pyrazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.22% In pyridine; acetone at 20℃;
  • 29
  • [ 83558-37-6 ]
  • [ 598-21-0 ]
  • 2-bromo-N-(4-(3-methoxyphenyl)thiazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64 mg Stage #1: 4-(3-methoxyphenyl)-2-aminothiazole With triethylamine In dichloromethane for 0.166667h; Inert atmosphere; Stage #2: 2-Bromoacetyl bromide In dichloromethane at 20 - 25℃; for 5h; Inert atmosphere; 31.ii ii) 2-Bromo-A/-(4-(3-methoxyphenyl)thiazol-2-yl)acetamide To a solution of 4-(3-methoxyphenyl)thiazol-2-amine (100 mg) in 7 mL dry DCM was added dropwise dry E3N (54 mg). After stirring for 10 min was added 2-bromoacetyl bromide (97 mg) and the resulting mixture was additional stirred for 5 h at RT. After completion of the reaction as monitored by LCMS water was added and the organic phase was separated. The water phase was extracted three times with DCM and the combined organic layers were dried with Na2S04, the solvent were removed under reduced pressure and the crude product was purified by silica gel chromatography using a gradient of ethyl acetate/cyclohexane as eluent. (0720) Yield: 64 mg MS (ES+) [M+H]+: m/e = 327.0, RT: 1.150 min
  • 30
  • [ 83558-37-6 ]
  • N-(4-(3-methoxyphenyl)thiazol-2-yl)-2-((4-oxo-3-phenethyl-3,4-dihydropteridin-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / Inert atmosphere 1.2: 5 h / 20 - 25 °C / Inert atmosphere 2.1: triethylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
  • 31
  • [ 83558-37-6 ]
  • [ 2927-71-1 ]
  • 4-(3-methoxyphenyl)-N-(5-fluoro-2-chloropyrimidin-4-yl)thiazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.1% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; 4 4-(3-methoxyphenyl)-N-(5-fluoro-2-chloropyrimidin-4-yl)thiazol-2-amine (II-4) In a test tube reactor, add 5-fluoro-2,4-dichloropyrimidine (0.166 g, 1 mmol), 4-(3-methoxyphenyl)-2-aminothiazole (0.206 g, 1 mmol), K2CO3 (0.207 g, 1.5mmol) and DMF (2ml), placed in an oil bath at 100 for 8h. To the reaction solution, 30 ml of ethyl acetate was added, washed 3 times with 30 ml of water, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and eluted with petroleum ether/ethyl acetate (V/V=10/1) as the elution The reagent was subjected to silica gel column chromatography to obtain the compound of formula (II-4) (0.178 g, yield 53.1%).
  • 32
  • α-phthalimido-o-toluoyl chloride [ No CAS ]
  • [ 83558-37-6 ]
  • 2-((1,3-dioxoisoindolin-2-yl)methyl)-N-(4-(3,4,5-trimethoxyphenyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine In dichloromethane at 20℃; 8.2.2 Synthesis of 2-((1,3-dioxoisoindolin-2-yl)methyl)-N-(4-arylthiazol-2-yl)benzamides 7a-h 8.2.2.1 General procedure General procedure: A mixture of compound 5 (0.16g, 0.534mmol), amino-thiazoles 6 (0.534mmol) and triethyl amine (TEA) (0.534mmol) in 15mL abs. Methylene chloride was stirred 4-8h at rt. The reaction was monitored by tlc. The reaction mixture was extracted with ethyl acetate, washed with brine, 1N HCl, NaHCO3 and finally with H2O. The solvent was evaporated and the residue was recrystallized from ethanol-chloroform to give the title compounds.
  • 33
  • 2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-(3-methoxylphenyl)ethan-1-one [ No CAS ]
  • [ 17356-08-0 ]
  • [ 83558-37-6 ]
YieldReaction ConditionsOperation in experiment
63% With bis(1,5-cyclooctadiene)diiridium(I) dichloride In 1,2-dichloro-ethane at 80℃; for 24h; Green chemistry; 2 Example 2: Synthesis of Compound 2 (1) Add (3-methoxy)phenylsulfur ylide in a clean reactor one by one(45.2 mg, 0.2 mmol), thiourea (30.4 mg, 0.4 mmol),Bis(1,5-cyclooctadiene) iridium chloride (I) dimer (4.0 mg, 0.006 mmol)And 1,2-dichloroethane (2 mL), put them in a 80°C oil bath and stir for 24 h.(2) After the reaction, collect the reaction liquid,Remove the solvent under reduced pressure,The residue was separated and purified by silica gel column chromatography to obtain a white color solid with a yield of 63%.
63% With dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; chemoselective reaction; 3. General Procedures for Annulation of Sulfoxonium Ylides and Thiourea General procedure: A mixture of substituted sulfoxonium ylides (1, 0.2 mmol, 1.0 equiv), thiourea (2,0.4 mmol, 2.0 equiv), Rh2(OAc)4 (5 mol%) were weighted in a Schlenk tube equipped with a stir bar. 1,2-Dichloroethane (1.5 mL) was added and the mixture was stirred at 80 °C for 24 h under air. After completion, the solvent of the reaction is distilled under reduced pressure. The purification was performed by flash column chromatography on silica gel with EtOAc/petroleum ether.
  • 34
  • [ 1711-05-3 ]
  • [ 83558-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / Reflux 1.2: 3 h / 0 - 20 °C 2.1: dirhodium tetraacetate / 1,2-dichloro-ethane / 24 h / 80 °C / Schlenk technique
  • 35
  • [ 83558-37-6 ]
  • 2-{4-[4-(1H-1,3-benzodiazol-2-yl)-2-methoxyphenoxymethyl]-1H-1,2,3-triazol-1-yl}-N-[2-(4-methoxyphenyl)-1,3-thiazol-5-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: sodium azide; triethylamine / water; <i>tert</i>-butyl alcohol / 1 h / 20 °C 3: triethylamine; copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 20 °C
  • 36
  • [ 83558-37-6 ]
  • N-[2-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-{4-[4-(6-methyl-1H-1,3-benzodiazol-2-yl)phenoxymethyl]-1H-1,2,3-triazol-1-yl}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: sodium azide; triethylamine / water; <i>tert</i>-butyl alcohol / 1 h / 20 °C 3: triethylamine; copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 20 °C
  • 37
  • [ 83558-37-6 ]
  • C12H11N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: sodium azide; triethylamine / water; <i>tert</i>-butyl alcohol / 1 h / 20 °C
  • 38
  • [ 83558-37-6 ]
  • 2-{4-[4-(1H-1,3-benzodiazol-2-yl)phenoxymethyl]-1H-1,2,3-triazol-1-yl}-N-[2-(4-methoxyphenyl)-1,3-thiazol-5-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: sodium azide; triethylamine / water; <i>tert</i>-butyl alcohol / 1 h / 20 °C 3: triethylamine; copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 20 °C
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