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Product Details of [ 1643-15-8 ]

CAS No. :1643-15-8 MDL No. :MFCD00014358
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VZECTCSEONQIPP-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :74235
Synonyms :

Calculated chemistry of [ 1643-15-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.48
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.14 mg/ml ; 0.00686 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.7 mg/ml ; 0.00421 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.842 mg/ml ; 0.00507 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 1643-15-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1643-15-8 ]

* 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 [ 1643-15-8 ]

[ 1643-15-8 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 110-86-1 ]
  • [ 1643-15-8 ]
  • [ 54914-85-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide at 30℃; Electrolysis;
  • 2
  • [ 67-56-1 ]
  • [ 1643-15-8 ]
  • [ 63051-20-7 ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid at 25℃; for 2h;
With hydrogenchloride
With toluene-4-sulfonic acid at 25℃; for 3h;
  • 3
  • [ 1643-15-8 ]
  • [ 40926-72-5 ]
YieldReaction ConditionsOperation in experiment
91% With thionyl chloride In benzene for 3h; Reflux;
With thionyl chloride
With thionyl chloride In ethyl acetate; benzene for 8h; Heating;
With thionyl chloride In methanol; ethyl acetate for 7h; Heating;
With thionyl chloride In methanol; ethyl acetate; benzene for 8h; Heating;
With thionyl chloride for 8h; Heating;
With thionyl chloride In benzene for 1h; Heating;
With thionyl chloride In chloroform Heating;
With thionyl chloride In benzene Heating;
With thionyl chloride In hexane Heating;
With thionyl chloride for 12h; 18.1 Excess thionyl chloride was added to two equivalents of substituted phenoxyacetic acid and was stirred for 12h. The reaction was concentrated and the corresponding acid chloride was added to a solution of one equivalent aromatic diamine and two equivalent of diisopropylethyl amine in anhydrous methylene chloride and stirred for 12 h. The reaction mixture was washed with IN HCI, 10% w/w NaHC03 and dried (MgS04), and concentrated in vacuo. The crude reaction was purified by flash chromatography (Si02, methylene chloride/methanol (98:2). The product identity and purity was confirmed by electrospray LC-MS using method A.
With thionyl chloride
With thionyl chloride at 80℃; for 4h; 3.1. Synthesis of the compound 3 series General procedure: The intermediates 2 were synthesized via methods reported previously.17 Compounds 2 (20 mmol) and thionyl chloride (15 mL, 200 mmol) were added to a 50 mL round-bottomed flask, the mixture was refluxed for 4 h, and then thionyl chloride was evaporated at reduced pressure. Anhydrous toluene (10 mL) was added to the acyl chloride, and the yielded solution was added dropwise to aqueous ammonia (10 mL) in a 100 mL three-necked flask equipped with a drying tube at 0-5 °C. The mixture was stirred at that temperature for another 1.5 h. After filtration the solvent was removed, the remaining residue was solved in hot acetone, the insoluble was discarded. Crude product was obtained by evaporating the solvent and purified by recrystallization from ethanol-water to obtain compounds 3.
With thionyl chloride for 6h; Reflux;
With thionyl chloride for 4h; Reflux; General Procedure forSynthesis of Compounds 51-54 General procedure: Phenoxyaceticacids (50 mmol) was added to thionylchloride (50 mL) at room temperature under a calcium chloride tube.The mixture was then heated under reflux for 4 h. After cooling to roomtemperature, the mixture was evaporated in vacuo. The residue was dissolved in50 mL of dichloromethaneand aluminium chloride (13 g, 98 mmol) was addedslowly to the solution at 0°C. After stirring at 0°C for 15min, the reactionstirred at room temperature for 30min. The mixture was then poured into icewater, extracted with portions of ethyl acetate (3×50 mL). The organic layerwas washed with brine, dried over anhydrous sodium sulfate and the solventremoved in vacuo. The residue was purified by column chromatography to get theproduct.
With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h; General procedure for the synthesis of HY-1a-HY-1f General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; General synthetic procedure for compounds 8-11 and 13-36 General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 °C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 °C. The solution was stirred for another 2 hrs at 25 °C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.
With thionyl chloride Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h;

Reference: [1]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[2]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541]
[3]Jain; Srivastava [Journal of the Indian Chemical Society, 1990, vol. 67, # 9, p. 775 - 776]
[4]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[5]Chaurasia; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 2, p. 106 - 107]
[6]Chaurasia, Sunita; Srivastava, Savitri D. [Journal of the Indian Chemical Society, 1992, vol. 69, # 1, p. 45 - 46]
[7]Osman; Botros; Kandeel; Khalil; Abd El-Latif [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 446 - 455]
[8]Bhatt, P.; Srivastava, S. D.; Mehta, P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 514 - 516]
[9]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]
[10]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]
[11]Current Patent Assignee: PARK FUNDING - WO2005/97119, 2005, A2 Location in patent: Page/Page column 62
[12]Location in patent: scheme or table He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[13]Location in patent: experimental part Li, Ting; Liu, Guyue; Li, Hongcai; Yang, Xinmei; Jing, Yongkui; Zhao, Guisen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2316 - 2322]
[14]Location in patent: experimental part Han, Liang; Zhu, Qiong-Yan; Jia, Jian-Hong; Li, Yu-Jin; Gao, Jian-Rong [Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1223 - 1226]
[15]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]
[16]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]
[17]Li, Zheng; Wang, Xuekun; Xu, Xue; Yang, Jianyong; Qiu, Qianqian; Qiang, Hao; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6666 - 6672]
[18]Sheng, Xijun; Zhou, Yuan; Zhang, Shasha; Peng, Hao; He, Hongwu [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 165 - 170]
[19]Noncovich, Alain; Priest, Chad; Ung, Jane; Patron, Andrew P.; Servant, Guy; Brust, Paul; Servant, Nicole; Faber, Nathan; Liu, Hanghui; Gonsalves, Nicole S.; Ditschun, Tanya L. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3931 - 3938]
[20]Lei, Kang; Li, Pan; Yang, Xue-Fang; Wang, Shi-Ben; Wang, Xue-Kun; Hua, Xue-Wen; Sun, Bin; Ji, Lu-Sha; Xu, Xiao-Hua [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 37, p. 10489 - 10497]
  • 4
  • [ 1643-15-8 ]
  • [ 13605-19-1 ]
YieldReaction ConditionsOperation in experiment
90% With borohydride exchange resin In methanol for 0.5h; Ambient temperature;
With lithium aluminium tetrahydride; diethyl ether
  • 5
  • [ 108-39-4 ]
  • [ 79-11-8 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide In ethanol; water for 4h; Heating;
85% With sodium hydroxide In water at 60℃; for 7h;
57% With potassium hydroxide In water Reflux; 4.1.3. Synthesis of Phenoxy Acetic Acid Derivatives (PAA1-PAA5) General procedure: The phenol derivative (19.2 mmol) was mixed with a solutionof potassium hydroxide (71.4 mmol, 4 g) in 8mL ofwater in a two necked round bottom flask until homogeneoussolution was produced. As the mixture began to boil, 6mL of50% w/v solution (g/ml) of chloroacetic acid was addeddrop-wise using dropping funnel placed in the side arm ofthe flask. The reaction mixture was refluxed until reactionwas completed (monitored by TLC). The solution was transferredto a beaker, cooled to room temperature and acidifiedby drop-wise addition of HCl (monitor using pH paper). Theresultant mixture was cooled in an ice bath, the crude productwas filtered and re-crystallized from boiling water.
With sodium hydroxide Erhitzen auf dem Dampfbad;
With alkali
With sodium hydroxide Heating;
With sodium hydroxide In water Heating;
With sodium hydroxide Heating;
With sodium hydroxide In water for 2h;
With sodium hydroxide
With potassium carbonate In acetone for 8h; Reflux;
With sodium hydroxide
With sodium hydroxide
Stage #1: 3-methyl-phenol; chloroacetic acid With sodium hydroxide at 100℃; Stage #2: With hydrogenchloride In water
Stage #1: 3-methyl-phenol With sodium hydroxide In water Stage #2: chloroacetic acid In water at 40 - 85℃; for 2h; Stage #3: With hydrogenchloride In water at 20℃; 4.5.1. Phenoxyacetic acids (7) General procedure: An appropriately substituted phenol (50 mmol) was added to a solution of NaOH (187.5 mmol) in 15 mL of H2O. Chloroacetic acid (85 mmol) was added slowly at to the resulting solution at 40 °C and the reaction mixture was heated to 85 °C. Stirring was continued for 2 h, the reaction was cooled to room temperature and 100 mL H2O was added. The reaction was filtered and the filtrate was acidified with concentrated HCl to pH 1-2. The brown oil fraction which formed was extracted to diethylether (2 × 50 ml). The ether fraction, in turn, was extracted with an aqueous solution of 5% Na2CO3 (2 × 37.5 ml). The combined Na2CO3 fractions were acidified to pH 1-2 with concentrated HCl and the resulting precipitate was collected by filtration and oven dried to obtain the required acids.24
With sodium hydroxide In water General procedure for the synthesis of aryloxy acetic/propionicacids (2a-q and 3a-q) General procedure: Equimolar quantities of 2-chloro acetic acid/3-chloro propionicacid (0.05 mol) and appropriate phenol (1a-q) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH(0.12 mol in 25 mL water) was slowly added with constant stirring.The solution was stirred for 2 h until the solution turned clear,brown or yellow and then the reaction mixture was evaporatedin a evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified byadding con. HCl. The precipitated aryloxy acetic/propionic acidwas filtered and recrystallized from water or ethanol

Reference: [1]Ramalingam, T.; Sattur, P. B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1204 - 1207]
[2]Del Carmen Cruz, María; Tamariz, Joaquín [Tetrahedron, 2005, vol. 61, # 42, p. 10061 - 10072]
[3]Singh, Gurmeet; Bansal, Yogita; Bansal, Gulshan; Goel, Rajesh Kumar [Medicinal Chemistry, 2014, vol. 10, # 4, p. 418 - 425]
[4]Koelsch [Journal of the American Chemical Society, 1931, vol. 53, p. 304]
[5]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541] Brueckner [Angewandte Chemie, 1928, vol. 41, p. 1046][Fresenius' Zeitschrift fuer Analytische Chemie, 1928, vol. 75, p. 290]
[6]BAKER; LEE; SKINNER; MARTINEZ; TONG [Journal of medicinal and pharmaceutical chemistry, 1960, vol. 2, p. 633 - 657]
[7]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[8]Purohit; Shah [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 618 - 622]
[9]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]
[10]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]
[11]Location in patent: body text Khanum, Shaukath Ara; Khanum, Noor Fatima; Shashikanth [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4597 - 4601]
[12]Location in patent: scheme or table Azam, M. Afzal; Suresh, Bhojraj; Kalsi, Sandip S.; Antony, A. Shinesh [South African Journal of Chemistry, 2010, vol. 63, p. 114 - 122]
[13]Location in patent: scheme or table He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[14]Location in patent: scheme or table Li, Ting; Liu, Guyue; Li, Hongcai; Yang, Xinmei; Jing, Yongkui; Zhao, Guisen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2316 - 2322]
[15]Location in patent: experimental part Okaecwe, Thokozile; Swanepoel, Abraham J.; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4336 - 4347]
[16]Joshi, Shrinivas D.; More, Uttam A.; Koli, Deepshikha; Kulkarni, Manoj S.; Nadagouda, Mallikarjuna N.; Aminabhavi, Tejraj M. [Bioorganic Chemistry, 2015, vol. 59, p. 151 - 167]
  • 13
  • [ 1643-15-8 ]
  • [ 588-20-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium chlorate In acetic acid
  • 15
  • [ 1643-15-8 ]
  • [ 158941-63-0 ]
  • 3-[2-hydroxy-4-phenyl-3-(2-<i>m</i>-tolyloxy-acetylamino)-butyryl]-thiazolidine-4-carboxylic acid <i>tert</i>-butylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide
  • 16
  • [ 63051-20-7 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In methanol
With water; sodium hydroxide Microwave irradiation;
With lithium hydroxide monohydrate In methanol; water for 2h; Reflux; General Procedure for Synthesis of Substituted acetamides (4a-4hh, 4' and 4'') General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH•H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.
With lithium hydroxide In methanol; water at 50℃; for 12h;

  • 17
  • [ 1643-15-8 ]
  • [ 36304-38-8 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In methanol for 25h; Heating;
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating
  • 18
  • [ 1643-15-8 ]
  • [ 2231-57-4 ]
  • 4-amino-5-mercapto-3-(3-tolyloxymethyl)-s-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% at 180℃; for 0.25h;
  • 19
  • [ 1643-15-8 ]
  • [ 98-09-9 ]
  • C15H14O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; PEG 400 In acetonitrile for 0.5h; Heating;
With potassium carbonate for 0.0833333h;
  • 20
  • [ 1643-15-8 ]
  • [ 16078-71-0 ]
  • 1-phenyl-5-(2-<i>m</i>-tolyloxy-acetylamino)-1<i>H</i>-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With phosphorus trichloride In xylene for 3h; Heating;
  • 21
  • [ 1643-15-8 ]
  • [ 713517-90-9 ]
  • 5-(2,6-dichloro-benzyl)-9b-phenyl-1-<i>m</i>-tolyloxy-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 0 - 20℃;
  • 22
  • [ 3926-62-3 ]
  • [ 108-39-4 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
75.7% With sodium hydroxide In ethanol; water for 1h; Reflux;
With sodium hydroxide In water at 60℃; for 8h;
  • 23
  • [ 66047-01-6 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: ethyl 3-methylphenoxyacetate With sodium hydroxide In tetrahydrofuran for 2h; Reflux; Stage #2: With hydrogenchloride In water
With potassium hydroxide In water for 1h; Heating;
With sodium hydroxide; water In methanol
With potassium hydroxide In ethanol; water at 20℃; for 1.5h; General procedure for the synthesis of 5a-f General procedure: A mixture of phenols (0.3 mmol), acetone (10 ml), dimethylformamide(10 ml), ethyl chloroacetate (2.5 ml, 0.26 mmol), potassiumcarbonate (2 g) and potassium iodide (0.15 g) was heated at75 C for 12 h. Afterwards, the solid was filtered and the solventof the filtrate was removed in vacuo. The colorless liquid (4a-f)obtained was dissolved in ethanol (20 ml). A solution of potassiumhydroxide (7.2%, 5 ml) was added and stirred at room temperaturefor 1.5 h. The mixture was poured into hydrochloric acid (1 mol/L)and a white precipitate was formed. Purification by recrystallizationfrom methanol afforded the corresponding aryloxyl acid (5a-f)
With sodium hydroxide In methanol at 20℃; for 0.166667h;

  • 24
  • [ 1643-15-8 ]
  • [ 79-19-6 ]
  • [ 84138-76-1 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 2-(m-tolyloxy)acetic acid; thiosemicarbazide With trichlorophosphate for 0.5h; Reflux; Stage #2: With water for 4h; Reflux;
With poly(ethylene glycol)-supported dichlorophosphate at 120℃; microwave irradiation;
With trichlorophosphate at 100℃; for 4h;
Stage #1: 2-(m-tolyloxy)acetic acid; thiosemicarbazide With trichlorophosphate at 75℃; for 0.5h; Stage #2: In water for 4h; Reflux; General procedure for the preparation of 2-((phenoxy orsubstituted phenoxy)methyl/ethyl)-1,3,4-thiadiazol-5-amines (4a-qand 5a-q) General procedure: A mixture of benzoic acid (50 mmol), N-aminothiourea(50 mmol) and POCl3 (13 mL) was heated at 75 C for 0.5 h. Themixture was cooled to which water (10 mL) was added and thereaction mixture was refluxed for 4 h. The mixture was cooled and pH was adjusted to 8.0 by adding 50% sodium hydroxide solution.The separated solid was filtered and recrystallized from ethanolto give desired compounds.

  • 25
  • [ 1643-15-8 ]
  • 3-(4-chlorophenyl)-4-amino-5-mercapto-[1,2,4]-triazole [ No CAS ]
  • C21H15N4O2SCl [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With trichlorophosphate microwave irradiation;
  • 26
  • [ 1643-15-8 ]
  • [ 79-03-8 ]
  • [ 1006585-37-0 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride In carbon disulfide
  • 27
  • [ 1643-15-8 ]
  • C13H14O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3 / CS2 2: 27.3 percent / K2CO3
  • 28
  • [ 1643-15-8 ]
  • [ 1148-36-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3 / CS2 2: 33.3 percent / K2CO3
  • 29
  • [ 1643-15-8 ]
  • 3-cyano-2,4-dimethyl-benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / hexane / Heating 2: 92 percent / CH2Cl2 / 12 h / 20 °C 3: 70 percent / 0.12 h / microwave irradiation
  • 30
  • [ 1643-15-8 ]
  • [ 826990-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / hexane / Heating 2: 92 percent / CH2Cl2 / 12 h / 20 °C
  • 31
  • [ 108-39-4 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / acetone / 3 h / Heating 2: potassium hydroxide / H2O / 1 h / Heating
  • 32
  • [ 1643-15-8 ]
  • rac-(SR)-[(5SR)-1-(2,6-dichlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-m-tolyloxyacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 99 percent / Et3N; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH2Cl2 / 0 - 20 °C 2: 82 percent / aq. LiOH / tetrahydrofuran; methanol / 45 - 60 °C
  • 33
  • [ 1643-15-8 ]
  • 5-amino-1-phenyl-6-<i>m</i>-tolyloxymethyl-1,5-dihydro-pyrazolo[3,4-<i>d</i>]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 62 percent / phosphorus trichloride / xylene / 3 h / Heating 2: 84 percent / hydrazine hydrate / butan-1-ol / Heating
  • 34
  • [ 1643-15-8 ]
  • 2-(3-methylphenyloxyacetylamido)-5-phenyloxymethyl-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating
  • 35
  • [ 1643-15-8 ]
  • 2-(3-methylphenyloxyacetylamido)-5-(4-methoxyphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating
  • 36
  • [ 1643-15-8 ]
  • 2-(3-methylphenyloxyacetylamido)-5-(2-methylphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating
  • 37
  • [ 1643-15-8 ]
  • 2-(3-methylphenyloxyacetylamido)-5-(4-methylphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating
  • 38
  • [ 1643-15-8 ]
  • 2-(3-methylphenyloxyacetylamido)-5-(1-naphthyloxymethyl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating
  • 39
  • [ 1643-15-8 ]
  • 3-(3-tolyloxymethyl)-6,11-dioxonaphtho[5,6:2,3][1,3,4]thiadiazino[2,3-c]-s-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / 0.25 h / 180 °C 2: 76 percent / Et3N / dimethylformamide / 12 h / Heating
  • 40
  • [ 1643-15-8 ]
  • [ 372164-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating 3: aq. HCl / 4 h / Heating 4: 85.3 percent / 8 percent aq. NaOH / 4 h / 95 °C
  • 41
  • [ 1643-15-8 ]
  • [ 372164-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating 3: aq. HCl / 4 h / Heating
  • 42
  • [ 1643-15-8 ]
  • 3-(3-methylphenoxymethyl)-4-N-[pyrazin-2-carboxamido]-1,2,4-triazole-5-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / conc. H2SO4 / methanol / 25 h / Heating 2: KOH / ethanol / 2 h 3: 68 percent / 6 h / 160 - 180 °C / Heating
  • 43
  • [ 1643-15-8 ]
  • 4-N-(3-methylphenoxymethyl carboxamido)-3-(pyrazin-2-yl)-1,2,4-triazole-5-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / conc. H2SO4 / methanol / 25 h / Heating 2: 82 percent / 8 h / 160 - 180 °C / Heating
  • 44
  • [ 1643-15-8 ]
  • C10H11N2O2S2(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / conc. H2SO4 / methanol / 25 h / Heating 2: KOH / ethanol / 2 h
  • 45
  • [ 1643-15-8 ]
  • [ 109395-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C
  • 46
  • [ 1643-15-8 ]
  • 3-amino-2-<i>m</i>-tolyloxymethyl-3<i>H</i>-quinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C 3: N2H4*H2O / ethanol / 6 h / Heating 4: ethanol / Heating
  • 47
  • [ 1643-15-8 ]
  • [ 1026862-02-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C 3: N2H4*H2O / ethanol / 6 h / Heating
  • 48
  • [ 1643-15-8 ]
  • 3-amino-2-<i>m</i>-tolyloxymethyl-5,6,7,8-tetrahydro-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C 3: N2H4*H2O / ethanol / 6 h / Heating 4: ethanol / Heating
  • 49
  • [ 1643-15-8 ]
  • [ 300828-26-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C
  • 50
  • [ 1643-15-8 ]
  • [ 1025937-20-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / benzene / Heating 2: acetic acid / 1 h / 0 - 5 °C 3: N2H4*H2O / ethanol / 6 h / Heating
  • 52
  • [ 1643-15-8 ]
  • 1-(2-m-Tolyloxy-acetyl)-pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3 / Heating 2: 76 percent / NaOH / toluene; methanol; acetone
  • 53
  • [ 1643-15-8 ]
  • C10H14N4O2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / benzene / 1 h / Heating 2: 86 percent / benzene / 4 h / Heating
  • 54
  • [ 1643-15-8 ]
  • [ 2021-05-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 8 h / Heating 2: 4N NaOH / H2O / 0.75 h
  • 55
  • [ 1643-15-8 ]
  • 1-Piperazin-1-yl-2-m-tolyloxy-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 8 h / Heating 2: 4N NaOH / H2O / 0.75 h
  • 56
  • [ 1643-15-8 ]
  • [ 137537-10-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / ethyl acetate; methanol / 7 h / Heating 2: 67 percent / 4N NaOH / methanol
  • 57
  • [ 1643-15-8 ]
  • [ 136776-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / benzene; ethyl acetate; methanol / 8 h / Heating 2: 70 percent / 4N NaOH / ethyl acetate; methanol; diethyl ether
  • 58
  • [ 1643-15-8 ]
  • [ 134145-74-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / benzene; ethyl acetate / 8 h / Heating 2: 2N NaOH / ethyl acetate
  • 59
  • [ 1643-15-8 ]
  • [ 20895-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride 2: aluminium chloride; carbon disulfide
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Reflux 2: aluminum (III) chloride / dichloromethane / 0.75 h / 0 - 20 °C / Reflux
  • 60
  • [ 1643-15-8 ]
  • [ 6500-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: bromine / chloroform 3: potassium acetate / methanol
  • 61
  • [ 1643-15-8 ]
  • [ 6464-28-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: bromine / chloroform
  • 63
  • [ 1643-15-8 ]
  • 3-Methyl-4-p-tolylthioacetylphenoxyessigsaeure [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide / ethanol
  • 64
  • [ 1643-15-8 ]
  • [ 6467-73-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide 3: (i) Me2NH*HCl, AcOH, iPrOH, (ii) aq. NaHCO3
  • 65
  • [ 1643-15-8 ]
  • [ 1681-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol / 100 °C
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol
  • 66
  • [ 1643-15-8 ]
  • [ 1237-51-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide / ethanol / Heating
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide / ethanol
  • 67
  • [ 1643-15-8 ]
  • [ 1237-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide / ethanol
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide
  • 68
  • [ 1643-15-8 ]
  • [3-Methyl-4-(2-phenylsulfanyl-acetyl)-phenoxy]-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide / ethanol / Heating
  • 69
  • [ 1643-15-8 ]
  • [ 6501-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aluminium trichloride / carbon disulfide 2: sodium hydroxide 3: (i) Me2NH*HCl, AcOH, iPrOH, (ii) aq. NaHCO3 4: hydrogenchloride
  • 70
  • [ 1643-15-8 ]
  • [ 6467-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol 3: acetic acid 4: sodium hydrogencarbonate
  • 71
  • [ 1643-15-8 ]
  • [ 801139-64-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol 3: acetic acid
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol / 100 °C 3: acetic acid / 100 °C
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol 3: acetic acid
Multi-step reaction with 3 steps 1: aluminium trichloride / carbon disulfide 2: potassium hydroxide / ethanol 3: acetic acid

  • 72
  • [ 1643-15-8 ]
  • [ 1151-81-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: acetic acid / 100 °C
Multi-step reaction with 2 steps 1: aluminium trichloride / carbon disulfide 2: acetic acid
  • 73
  • [ 1093076-74-4 ]
  • [ 1643-15-8 ]
  • [ 820220-85-7 ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
  • 74
  • [ 5440-00-6 ]
  • [ 1643-15-8 ]
  • C15H18N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4,5-Diamino-1,3-dimethyluracil; 2-(m-tolyloxy)acetic acid With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,4-dioxane; water at 20℃; for 2h; Stage #2: With sodium hydroxide In 1,4-dioxane; water 4.2. Synthesis of 8-phenoxymethylcaffeine derivatives (3a-j) General procedure: The syntheses of 3a-j were accomplished using the literature procedure.22 1,3-Dimethyl-5,6-diaminouracil23 (4 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDAC; 5.36 mmol) were dissolved in 42 mL dioxane/H2O (1:1) and the appropriate phenoxyacetic acid (4 mmol) was added. A thick suspension was obtained and the pH was adjusted to 5-6 with 4 N aqueous HCl. The reaction was stirred for 2 h at room temperature and neutralized with aqueous NaOH (1 N). The precipitate was collected by filtration and subsequently dissolved in 40 mL dioxane/H2O (1:1). The reaction was heated under reflux for 2 h, cooled to 0 °C and acidified to a pH of 4 with 4 N aqueous HCl. The resulting precipitate, the corresponding 1,3-dimethyl-8-substituted-7H-xanthinyl analogue, was collected by filtration, washed with 50 mL H2O and dried at 50 °C. The 7H-xanthinyl analogue was used in the subsequent reaction without further purification. The corresponding 1,3-dimethyl-8-substituted-7H-xanthinyl analogue (2 mmol) was dissolved in a minimum amount of DMF (approximately 20 mL) at 90 °C. K2CO3 (5 mmol), followed by iodomethane (4 mmol), and the reaction mixture was stirred at 90 °C for 1 h. The reaction progress was followed with TLC employing neutral alumina sheets and ethyl acetate/dichloromethane (1:1) as mobile phase. The insoluble materials were removed by filtration. H2O (350 ml) was added to the filtrate and the mixture was cooled on ice for 3 h. The precipitate that formed was collected by filtration and dried overnight at room temperature. The products were recrystallized from methanol/ethyl acetate (7:5).
  • 75
  • [ 1643-15-8 ]
  • [ 622-52-6 ]
  • [ 1392217-13-8 ]
YieldReaction ConditionsOperation in experiment
78% With iron(III) chloride hexahydrate In ethyl acetate at 80℃; for 10h;
  • 76
  • [ 1643-15-8 ]
  • [ 3696-23-9 ]
  • [ 1392217-19-4 ]
YieldReaction ConditionsOperation in experiment
78% With iron(III) chloride hexahydrate In ethyl acetate at 80℃; for 9h;
  • 77
  • [ 108-39-4 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 2 h / Reflux 2.2: pH 1
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C 2: lithium hydroxide monohydrate / methanol; water / 2 h / Reflux
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 12 h / 75 °C 2: potassium hydroxide / ethanol; water / 1.5 h / 20 °C
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 8 h / Reflux 2: hydrogenchloride / water / pH 1
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C 1.2: 12 h / 50 °C 2.1: lithium hydroxide / methanol; water / 12 h / 50 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2: sodium hydroxide / methanol / 0.17 h / 20 °C

  • 78
  • [ 1643-15-8 ]
  • [ 130-15-4 ]
  • [ 1449692-24-3 ]
YieldReaction ConditionsOperation in experiment
89% With ammonium peroxydisulfate; silver nitrate In water; acetonitrile at 80℃; for 0.0833333h;
  • 79
  • [ 2963-77-1 ]
  • [ 1643-15-8 ]
  • [ 654053-36-8 ]
YieldReaction ConditionsOperation in experiment
47% General procedure: The mixture of 0.1mol of phenoxy acetic acid derivative(PAA1-PAA5) and 0.1mol of dicyclohexyl carbodiimide in10 mL dichloromethane was stirred at room temperature.After 30 minutes, a solution of AB or APB in 20 ml of dichloromethaneand 5 ml of pyridine was added. The reactionmixture was stirred initially at 0C for 2 h followed by stirring at room temperature for 12 h. The precipitated dicyclohexylureawas removed by filtration and the solvent wasdistilled at reduced pressure on rotary vacuum evaporator.The dried product was dissolved in ethyl acetate (10 mL) andthe solution was washed with 10% aqueous solution of sodiumbicarbonate followed by distilled water to remove thetraces of residual dicyclohexylurea. The ethyl acetate layerwas dried with anhydrous magnesium sulphate and then solventwas distilled off to obtain the crude product which wasrecrystallized from ethanol-water mixture.
  • 80
  • [ 934-32-7 ]
  • [ 1643-15-8 ]
  • [ 70345-66-3 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2-(m-tolyloxy)acetic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Stage #2: 1H-benzimidazol-2-amine With pyridine In dichloromethane at 0 - 20℃; for 14h; 4.1.4.Synthesis of Target Compounds (AB and APB Series) General procedure: The mixture of 0.1mol of phenoxy acetic acid derivative(PAA1-PAA5) and 0.1mol of dicyclohexyl carbodiimide in10 mL dichloromethane was stirred at room temperature.After 30 minutes, a solution of AB or APB in 20 ml of dichloromethaneand 5 ml of pyridine was added. The reactionmixture was stirred initially at 0°C for 2 h followed by stirring at room temperature for 12 h. The precipitated dicyclohexylureawas removed by filtration and the solvent wasdistilled at reduced pressure on rotary vacuum evaporator.The dried product was dissolved in ethyl acetate (10 mL) andthe solution was washed with 10% aqueous solution of sodiumbicarbonate followed by distilled water to remove thetraces of residual dicyclohexylurea. The ethyl acetate layerwas dried with anhydrous magnesium sulphate and then solventwas distilled off to obtain the crude product which wasrecrystallized from ethanol-water mixture.
  • 81
  • [ 1643-15-8 ]
  • [ 530-62-1 ]
  • [ 139554-51-1 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃; for 1h; General Procedure for Synthesis of Substituted acetamides (4a-4hh, 4' and 4'') General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH•H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.
In tetrahydrofuran for 1h;
In acetonitrile at 20℃; for 8h;
  • 82
  • [ 96-32-2 ]
  • [ 108-39-4 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; General Procedure forSynthesis of Compounds 47-50 General procedure: To a solution of phenols (50 mmol) in DMF (80 mL) was added potassium carbonate(10.4 g, 75 mmol) and methyl bromoacetate (5.7 mL, 60mmol). After stirring at room temperature for 12 h, the solution was dilutedwith ethyl acetate (200 mL) and washed with brine, dried over anhydrous sodiumsulfate, filtered and concentrated under vacuum to afford the productas awhite solid.
  • 83
  • [ 58590-46-8 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In water 2.1 Synthesis of phenoxyacetic acid and ring-substituted phenoxyacetic acids General procedure: General procedure: To a solution of phenol or ring-substituted phenol (20 mmol) in water (20 mL) was added sodium chloroacetate (22 mmol) at rt. The mixture was heated and stirred at reflux for 8 h. The reaction mixture was cooled and the pH was adjusted to a value of 1.0 with 5 N HCl. The solution was filtered and the obtained solid was recrystallized from dehydrated ethanol to afford the pure product. 3-Methylphenoxyacetic acid (1l) Following the general procedure the compound 1l was obtained in 74 % yield as a white solid. m.p. 135-137 °C. 1H NMR (400 MHz, CDCl3) δ 9.42 (s, 1H), 7.19 (t, J = 7.90 Hz, 1H),6.84 (d, J = 7.5 Hz, 1H), 6.81-6.67 (m, 2H), 4.67 (s, 2H), 2.34 (s, 3H).MS (ESI) m/z: 166 [M]+. (S4)
  • 84
  • [ 1643-15-8 ]
  • [ 504-02-9 ]
  • C15H16O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine; 2-hydroxy-2-methylpropanenitrile; 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 12h;
  • 85
  • [ 105-36-2 ]
  • [ 108-39-4 ]
  • [ 1643-15-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl bromoacetate; 3-methyl-phenol With potassium carbonate In dimethyl sulfoxide at 50℃; for 6h; Stage #2: With water; sodium hydroxide In acetone at 50℃; for 3h; Stage #3: With hydrogenchloride In water at 25℃;
  • 86
  • [ 1643-15-8 ]
  • N-(thiophen-2-ylmethyl)-1H-pyrazol-3-amine [ No CAS ]
  • N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(m-tolyloxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(m-tolyloxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at -45 - 20℃; for 3h; Inert atmosphere; Stage #2: N-(thiophen-2-ylmethyl)-1H-pyrazol-3-amine In dichloromethane at 110℃; Inert atmosphere; 1.1 Example 1.1: Synthesis and Characterization of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(m-tolyloxy)acetamide (Compound 101) 2-(m-tolyloxy)acetic acid (1.25 g, 7.52 mmol, 1 equiv) was suspended in anhydrous dichloromethane (DCM; 40 mL) under nitrogen and cooled to -45° C. CDI (1.26 g, 7.77 mmol, 1.03 equiv) was then added as a solution in anhydrous DCM (18 mL). The mixture was allowed to warm to room temperature and then stirred for 3 hours. Approximately 95% of the DCM solvent was then removed under vacuum to give a residue. To this residue was then added N-(thiophen-2-ylmethyl)-1H-pyrazol-3-amine (1.62 g, 9.04 mmol, 1.2 equiv) dissolved in anhydrous DCM (15 mL). The mixture was heated to a 110° C. in an oil bath, under nitrogen, set up in a way which allowed all the DCM to escape, to give a neat reaction mixture, which was stirred overnight. The resulting residue was then dissolved in MeOH and purified by HPLC using a 0.1% formic acid in water: ACN gradient (35% ACN to 45% ACN over 30 minutes). The pure fractions were combined, and sodium carbonate was added until basic, in order to neutralize all the formic acid. The ACN was then removed under vacuum, but the water layer was left behind and extracted with DCM. The DCM was then washed with brine, dried with magnesium sulfate, and concentrated to give a residue. The residue was dissolved in a mixture of EtOH and water, then frozen, and lyophilized to give the product as a solid. 1H NMR (DMSO-d6, 400 MHz): 12.90 (s, 1H), 7.79 (s, 1H), 7.41 (m, 1H), 7.12 (t, J=7.6 Hz, 1H), 6.91 (m, 2H), 6.73 (m, 1H), 6.58 (m, 2H), 6.23 (s, 1H), 4.98 (s, 2H), 4.61 (s, 2H), 2.23 (s, 3H) ppm. MS=328 (MH+)
  • 87
  • [ 58255-25-7 ]
  • [ 1643-15-8 ]
  • [ 1374762-60-3 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation;
  • 88
  • [ 1643-15-8 ]
  • tert-butyl 3-(4-[hydrazinyl(thioxo)acetyl]amino}phenyl)propanoate [ No CAS ]
  • 3-{4-[({5-[(3-methylphenoxy)methyl]-1,3,4-thiadiazol-2-yl}carbonyl)amino]phenyl}propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 2-(m-tolyloxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 3-(4-[hydrazinyl(thioxo)acetyl]amino}phenyl)propanoate In dichloromethane at 20℃; for 16h; Inert atmosphere; Further stages; General procedure for the preparation of compounds 4a-uand 5a-q General procedure: To a solution of the respective carboxylic acid (8a-u or 9,0.5 mmol) in DCM (4 mL) carbonyl-1,10-diimidazole (0.55 mmol,90 mg) was added and the mixture was stirred at r. t. for 30 min. Tothe resulting solution of the carboxylic acid imidazolide, respectivethiohydrazide (7 or 10a-q) was added and the reaction mixturewasstirred at r. t. for 16 h. The solvent was removed in vacuo, the residuewasdissolved in glacial acetic acid (3 mL) and the solutionwasheated at reflux for 30 min. It was then cooled down to r. t., pouredinto water (50 mL), the resulting precipitate was collected byfiltration and dried in vacuo. It was then combined with 4 M solutionof HCl in 1,4-dioxane (5 mL); the mixture was stirred at r. t.for 16 h and poured into water (50 mL). The precipitate wascollected by filtration, washed with water and air-dried to providethe title compounds in yields indicated.
  • 89
  • [ 1643-15-8 ]
  • 3-(3-((4-chlorophenoxy)methyl)-1,2,4-oxadiazol-5-yl)bicyclo[1.1.1]pentan-1-amine [ No CAS ]
  • N-(3-{3-[(4-chlorophenoxy)methyl]-1,2,4-oxadiazol-5-yl}bicyclo[1.1.1]pentan-1-yl)-2-(3-methylphenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 20℃; for 18h; 3.3D Example 3D: N-(3-{3-[(4-chlorophenoxy)methyl]-l,2, 4-oxadiazol-5-yl}bicyclo[ 1.1.1 Jpentan-1- yl)-2-(3-methylphenoxy)acetamide To a solution of 2-(m-tolyloxy)acetic acid (16.7 mg, 0.101 mmol) in N,N- dimethylacetamide (0.5 mL) was added N,N-diisopropylethylamine (0.064 mL, 0.366 mmol), l-[bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3-oxid (0579) hexafluorophosphate (104 mg, 0.274 mmol) and Example 3C (30.1 mg, 0.091 mmol). The reaction was stirred at room temperature for 18 hours. The crude reaction was purified by HPLC (2-coupled C8 5 μηι 100 A columns 30 mm χ 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1% trifluoroacetic acid in water)). XH NMR (400 MHz, DMSO-c) δ ppm 8.94 (s, 1H), 7.39 - 7.30 (m, 2H), 7.17 (t, J = 8.0 Hz, 1H), 7.10 - 7.01 (m, 2H), 6.83 - 6.70 (m, 3H), 5.23 (s, 2H), 4.41 (s, 2H), 2.53 (s, 6H), 2.27 (s, 3H). MS (APCI) m/z 440.300 (M+H)+.
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; for 18h; 3D Example 3D: N-(3-[3-[(4-chlorophenoxy)methyl]-1, 2, 4-oxadiazol-5-yl]bicyclo[1. 1.] ]pentan-1 - yl)-2-(3-methylphenoxy)acetamide To a solution of 2-(m-tolyloxy)acetic acid (16.7 mg, 0.10 1 mmol) in N,Ndimethylacetamide (0.5 mL) was added N,N-diisopropylethylamine (0.064 mL, 0.3 66 mmol), 1-[bis(dimethylamino)methylenel - 1H- 1,2,3 -triazolo [4,5 -blpyridinium 3-oxid hexafluorophosphate(104 mg, 0.274 mmol) and Example 3C (30.1 mg, 0.091 mmol). The reaction was stirred atroom temperature for 18 hours. The crude reaction was purified by HPLC (2-coupled C8 5 jim100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrilein buffer (0.1% trifluoroacetic acid in water)). ‘H NMR (400 MHz, DMSO-d6) ö ppm 8.94 (s,1H), 7.39 -7.30 (m, 2H), 7.17 (t, J = 8.0 Hz, 1H), 7.10 -7.01 (m, 2H), 6.83 - 6.70 (m, 3H), 5.23(s, 2H), 4.41 (s, 2H), 2.53 (s, 6H), 2.27 (s, 3H). MS (APCI) m/z 440.300 (M+H)
  • 90
  • [ 1643-15-8 ]
  • N-(3-aminobicyclo[1.1.1 ]pentan-1-yl)-2-(4-chlorophenoxy)acetamide [ No CAS ]
  • 2-(4-chlorophenoxy)-N-{3-[2-(3-methylphenoxy)acetamido]bicyclo[1.1.1]-pentan-1-yl}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 20℃; for 18h; 15 Example 15: 2-(4-chlorophenoxy)-iV-{3-[2-(3-methylphenoxy)acetamido]bicyclo[l.l.l]- pentan-l-yl}acetamide (Compound 114) Example 15: 2-(4-chlorophenoxy)-iV-{3-[2-(3-methylphenoxy)acetamido]bicyclo[l.l.l]- pentan-l-yl}acetamide (Compound 114) To a solution of 2-(m-tolyloxy)acetic acid (13.7 mg, 0.0801 mmol) in N,N- dimethylacetamide (0.5 mL) was added N,N-diisopropylethylamine (0.052 mL, 0.299 mmol), l-[bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-/)]pyridinium 3-oxid [0790] hexafluorophosphate (71.3 mg, 0.187 mmol) and Example 14B (20.1 mg, 0.0701 mmol). The reaction was stirred at ambient temperature for 18 hours. The crude reaction was purified by HPLC (2-coupled C8 5 μπι 100 A columns 30 mm χ 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1% trifluoroacetic acid in water)). XH NMR (400 MHz, DMSO-c) δ ppm 8.74 (d, J = 17.9 Hz, 2H), 7.39 - 7.27 (m, 2H), 7.16 (t, J = 8.1Hz, 1H), 7.05 - 6.91 (m, 2H), 6.86 - 6.64 (m, 3H), 4.39 (d, J = 16.7 Hz, 4H), 2.26 (m, 9H). MS (APCI) m/z 415.370 (M+H)+.
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; for 18h; 15 Example 15: 2-(4-chlorophenoxy)-N-{3-[2-(3-methylphenoxy)acetamido]bicyclo[l.l.l]- pentan-l-yl}acetamide (Compound 114) To a solution of 2-(m-tolyloxy)acetic acid (13.7 mg, 0.0801 mmol) in N,N- dimethylacetamide (0.5 mL) was added N,N-diisopropylethylamine (0.052 mL, 0.299 mmol), 1- [bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-]pyridinium 3-oxid hexafluorophosphate (71.3 mg, 0.187 mmol) and Example 14B (20.1 mg, 0.0701 mmol). The reaction was stirred at ambient temperature for 18 hours. The crude reaction was purified by HPLC (2-coupled C8 5 μπι 100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1% trifluoroacetic acid in water)).JH NMR (400 MHz, DMSO- ) δ ppm 8.74 (d, J = 17.9 Hz, 2H), 7.39 - 7.27 (m, 2H), 7.16 (t, J = 8.1 Hz, 1H), 7.05 - 6.91 (m, 2H), 6.86 - 6.64 (m, 3H), 4.39 (d, J = 16.7 Hz, 4H), 2.26 (m, 9H). MS (APCI) m/z 415.370 (M+H)+
  • 91
  • [ 1643-15-8 ]
  • [ 518-28-5 ]
  • 8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,7,8,8a,9-hexahydrofuro[2’,3’:6,7]naphtho[2,3-d][1,3]dioxol-5-yl 2-(m-tolyloxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; General procedure for preparation of compoundsM1-M16 General procedure: Fibiric acids derivatives L1-L16 (0.015 mol), podophyllotoxin(0.01 mol), 4-dimethyaminopyridine (DMAP) (0.001mol) and N,N-dicyclohexylcarbodiimide (DCC) (0.02 mol)were dissolved in dichloromethane (30 mL) and stirred for12 h at room temperature. Then, a proper amount of silicagel were added and the solvent was condensed by vacuumconcentration. Finally, the target compounds were collectedby column chromatography (V(acetone): V(dichloromethane)= 1: 50). Chemical structures of the targetcompounds (M1-M16) were shown in Fig. 2. All the targetcompounds were reported for the first time.
  • 92
  • [ 1643-15-8 ]
  • [ 797-63-7 ]
  • (13S,17R)-13-ethyl-17-ethynyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl (3-methylphenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; (General Method 2): General procedure: To a round bottom flaskwas added 1 (1.41 g, 4.5 mmol), (3-methyl-phenoxy)acetic acid (3.0 g,18.1 mmol), and DMAP (550 mg, 4.5 mmol) in DCM (30 ml) at ambienttemperature. Once a homogenous solution was observed, DIC wasadded (2.8 ml, 18.1 mmol). The mixture was allowed to stir overnight.The next morning the mixture was filtered, and the filtrate was rotovapedonto silica gel and subjected to flash chromatography. The resultantfoam was then crystallized from methanol and DCM yielding1.08 g of white crystal (73%). 1H NMR (300 MHz, CDCl3) δ 7.17 (t,J=7.5 Hz, 1H), 6.81 (d, J=7.2 Hz, 1H), 6.73-6.67 (m, 2H), 5.84 (s,1H), 4.59 (s, 2H), 2.66 (s, 1H), 2.33 (s, 3H). IR (cm-1): 3227, 1775,1658, 1611, 1259, 1196, 1158, 1095, 785, 688. MP 187-190 °C.
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; (13S,17R)-13-ethyl-17-ethynyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl (3-methylphenoxy)acetate (General Method No.2) (13S,17R)-13-ethyl-17-ethynyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl (3-methylphenoxy)acetate (General Method No.2) To a round bottom flask was added 1 (1.41 g, 4.5 mmol), (3-methylphenoxy)acetic acid (3.0 g, 18.1 mmol), and DMAP (550 mg, 4.5 mmol) in DCM (30 mL) at ambient temperature. Once a homogenous solution was observed, DIC was added (2.8 ml, 18.1 mmol). The mixture was allowed to stir overnight. The next morning the mixture was filtered, and the filtrate was rotovaped onto silica gel and subjected to flash chromatography. The resultant foam was then crystallized from methanol and DCM yielding 1.08 g of white crystal 5 (73%). 1H NMR (300 MHz, CDCl3) δ 7.17 (t, J=7.5 Hz, 1H), 6.81 (d, J=7.2 Hz, 1H), 6.73-6.67 (m, 2H), 5.84 (s, 1H), 4.59 (s, 2H), 2.66 (s, 1H), 2.33 (s, 3H).
  • 93
  • [ 139554-51-1 ]
  • [ 1643-15-8 ]
  • [ 1415419-08-7 ]
  • (R)-1-nitro-3-(m-tolyloxy)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C 2: glucose dehydrogenase; D-glucose; YGL039w from saccharomyces cerevisiae; nicotinamide adenine dinucleotide phosphate / aq. acetate buffer / 1 h / 30 °C / pH 5 / Enzymatic reaction
  • 94
  • [ 1643-15-8 ]
  • [ 1415419-08-7 ]
  • (R)-1-nitro-3-(m-tolyloxy)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C 3: glucose dehydrogenase; D-glucose; YGL039w from saccharomyces cerevisiae; nicotinamide adenine dinucleotide phosphate / dimethyl sulfoxide / 1 h / 30 °C / Enzymatic reaction
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C 3: glucose dehydrogenase; D-glucose; YGL039w from saccharomyces cerevisiae; nicotinamide adenine dinucleotide phosphate / aq. acetate buffer / 1 h / 30 °C / pH 5 / Enzymatic reaction
  • 95
  • [ 1643-15-8 ]
  • [ 1415419-08-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C 3: glucose dehydrogenase; D-glucose; SyADH from sphingobium yanoikuyae; nicotinamide adenine dinucleotide phosphate / dimethyl sulfoxide / 1 h / 30 °C / Enzymatic reaction
  • 96
  • [ 1643-15-8 ]
  • 1-nitro-3-(m-tolyloxy)propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C
  • 97
  • [ 1643-15-8 ]
  • 1-nitro-3-(m-tolyloxy)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 24 h / 20 °C 3: sodium tetrahydroborate / methanol / 20 °C
  • 98
  • 1-nitro-3-(m-tolyloxy)propan-2-one [ No CAS ]
  • [ 1643-15-8 ]
  • [ 1415419-08-7 ]
  • (R)-1-nitro-3-(m-tolyloxy)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85 % ee With glucose dehydrogenase; D-glucose; YGL039w from saccharomyces cerevisiae; nicotinamide adenine dinucleotide phosphate In aq. acetate buffer at 30℃; for 1h; Enzymatic reaction; stereoselective reaction;
  • 99
  • [ 462-08-8 ]
  • [ 1643-15-8 ]
  • 2-(3-methylphenoxy)-N-(3-pyridyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
  • 100
  • [ 23687-26-5 ]
  • [ 1643-15-8 ]
  • N-(6-isoquinolyl)-2-(3-methylphenoxy)acetamide [ No CAS ]
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