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Product Details of [ 614-61-9 ]

CAS No. :614-61-9 MDL No. :MFCD00004298
Formula : C8H7ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OPQYFNRLWBWCST-UHFFFAOYSA-N
M.W : 186.59 Pubchem ID :11969
Synonyms :

Calculated chemistry of [ 614-61-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.52
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) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.852 mg/ml ; 0.00456 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.649 mg/ml ; 0.00348 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.547 mg/ml ; 0.00293 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 614-61-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 614-61-9 ]

* 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 [ 614-61-9 ]

[ 614-61-9 ] Synthesis Path-Downstream   1~101

  • 2
  • [ 614-61-9 ]
  • [ 64-17-5 ]
  • [ 52094-97-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;Reflux; General procedure: Each substituted benzoic acid or aroyloxy acetic acid (7a-s) 0.088 mol was refluxed for 2-12 h in 2.4 mol of HCl gas saturated anhydrous ethanol. Then a hot solution was poured into 300 mL of water (no hydrochloride separates) to which solid Na2CO3 was added until the solution turns neutral. Precipitated ester was filtered by suction, dried and recrystallized from ethanol or methanol. In case of liquid esters, the neutralized solution was extracted with chloroform (25 mL x 3), the combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a clear liquid.
With sulfuric acid; for 6h;Reflux; General procedure: The substituted acid (0.1 mole) and ethanol (50 ml) were taken with a few drops of concentrated sulfuric acid and it was refluxed for 6 hours.The reaction mixture was concentrated bydistilling of the excess of ethanol under reduced pressure and treated with a saturated solution of sodium bicarbonate. The ester obtained used for the preparation of hydrazide directly. The ester(0.1 mole) was dissolved in appropriate quantity of ethanol and to this hydrazine hydrate (0.1 mole) was added. The reaction mixture was taken in a round bottomed flask and refluxed for a period of 12-18 hours. Excess of ethanol was distilled off under reduced pressure. It was then poured into ice cold water and the solid obtained was filtered. It was crystallized from ethanol.
  • 3
  • [ 614-61-9 ]
  • [ 94-75-7 ]
YieldReaction ConditionsOperation in experiment
99.7% With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; In acetonitrile; at 20 - 25℃; for 0.0833333h;Green chemistry; General procedure: To a solution of 4-nitroaniline, 1a (0.99 g, 7.2 mmol) in 7 mL specially dried MeCN was added N-chloro-N-(phenylsulfonyl)benzene sulfonamide (2.4 g, 7.2 mmol) in a 25 mL round bottom flask. The reaction mixture was stirred for 10-15 minutes at 20-25 C (0 C for 1-methyl-1H-imidazole, and N-methylindole), monitored by GC. After completion of the reaction, MeCN was distilled under vacuum at 40-45 C. The residue was treated with 20 mL mixture of MDC and water, stirred the mixture for 10-15 minutes; MDC layer was separated and washed with 5 % sodium bicarbonate solution, after separation MDC layer was dried over sodium sulfate and evaporated under vacuum to obtain 2-chloro-4-nitroaniline, 2a, 1.22 g (98.5 % yield, 98.9 % purity) as a yellow powder.
  • 4
  • [ 614-61-9 ]
  • [ 18800-42-5 ]
  • 5
  • [ 614-61-9 ]
  • [ 5037-04-7 ]
YieldReaction ConditionsOperation in experiment
With nitric acid
  • 6
  • [ 614-61-9 ]
  • [ 20143-41-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;Reflux; General procedure: The 2-amino-5-mercapto-1,3,4-thiadiazole 1 (5 mmol) was dissolved in NaOH(5 mmol, 15 mL) at room temperature. Ethyl 2-bromopropionate (5 mmol) was addedto the solution obtained and the mixture was stirred for 20 min. After that, the solid precipitatewas filtered off, washed with cold water, air dried, and then recrystallized from ethanolto give 2-(5-amino-1,3,4-thiadiazol-2-ylthio) propanoate 2 in 78% yield as pale yellowsolid. Mp 79-80C; 1H NMR(CDCl3, 400 MHz) δH: 1.25-1.28 (t, 3H, CH3, J = 6.0 Hz),1.57-1.59 (d, 3H, CH3, J = 8.0 Hz), 4.03-4.08 (q, 1H, SCH, J = 12.0 Hz), 4.16-4.22(q, 2H, OCH2, J = 16.0 Hz).4.35 (s, 2H, NH2); 13C NMR (CDCl3, 400 MHz) δC: 14.0,17.5, 46.0, 61.8, 150.0, 170.9, 171.4; IR (KBr) ν: 3266 (NH2), 1736 (OC O), 1501,1449, 1321, 1094 (C N N C S) cm-1; Anal. calcd for C7H11N3O2S2: C36.04, H 4.75,N 18.01; found C 36.10, H 4.77, N 17.93.To a 50 mL round-bottom flask was added phenoxyalkanoic acid 4 (5 mmol) andSOCl2 (5 mL). The mixture was refluxed for 4 h, and the excess SOCl2 was removedunder vacuum. The crude diacyl chloride was dissolved in CH3CN (5 mL) and addeddropwise through a dropping funnel to themixture of 2-(5-amino-1,3,4-thiadiazol-2-ylthio)propanoate 2 (4.5 mmol) and Et3N (4.2 mL, 30 mmol) in CH3CN (15 mL) on an ice bath.This mixture was vigorously stirred at room temperature for an additional 12 h aftercompletion of the addition. The product was evaporated under reduced pressure washedwith water and brine, dried and recrystallized from ethanol to give the title compounds 6.
With phosphorus pentachloride; In dichloromethane;Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
With thionyl chloride; In toluene;Reflux; Acid 2 (2.20mmol; 0.42g) was dissolved in 12mL toluene and SOCl2 (82.3mmol; 6.00mL) was added. The mixture was refluxed overnight, and the solvent was removed on high vacuum to give the crude acyl chloride. This product was dissolved in a small amount of THF and added to a solution of methyl 2-amino-4-cyanobenzoate (2.00mmol; 0.35g) and K2CO3 (4.00mmol; 0.55g) in THF (29ml) stirred for 15minat RT. The reaction mixture was stirred at RT for 4h until the reaction was complete. The reaction was diluted with water (30mL) and extracted with EtOAc (3×30mL). The combined organics were washed with brine, dried with Na2SO4 and evaporated to dryness. The crude product was recrystallized in acetonitrile to give white crystals (0.55g; 80%). 1H NMR (400MHz, CDCl3) δ 11.90 (s, 1H), 9.16 (d, J=1.4Hz, 1H), 8.13 (d, J=8.2Hz, 1H), 7.42 (ddd, J=12.3, 8.0, 1.5Hz, 2H), 7.25 (td, J=8.0, 1.6Hz, 1H), 7.05-6.96 (m, 2H), 4.72 (s, 2H), 3.95 (s, 3H). 13C NMR (101MHz, CDCl3) δ 167.45, 166.71, 153.10, 140.55, 131.72, 130.96, 128.10, 126.38, 124.51, 123.86, 123.53, 119.61, 117.77 (d, J=5.3Hz), 114.82, 69.11, 53.13. HRMS m/z [M+ H]+ calcd for C17H14ClN2O4 345.0637, found: 345.0627. mp: 159.6-160.1C.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 3h; General procedure: To a solution of the acid (22a-g) (1.2 eq.) in DCM, oxalyl chlorideand 1 drop DMF were added dropwise at 0 C. After 3 h, DCM wasremoved by rotary evaporation. The resulting acyl chloride dissolvedin THF and pyridine was added dropwise into a solution of26 (1.0 eq.) in THF at 0 C, then slowly warmed to r.t. and continuedstirring for 5e6 h. 1 M HCl was added and extracted with ethylacetate for three times. The organic layer was combined, washedwith brine for once, dried over anhydrous Na2SO4 and concentratedto afford compounds 27a-g. To the solution of 27a-g in ethyl acetate,HCl gaswas added for 0.5 h, and the resulting solidwas filteredto obtain desired compounds 28a-g.

Reference: [1]Journal of the Chemical Society,1922,vol. 121,p. 1603
[2]Journal of Medicinal Chemistry,1972,vol. 15,p. 940 - 944
[3]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4426 - 4434
[4]Archiv der Pharmazie,1983,vol. 316,p. 431 - 434
[5]Journal of the Indian Chemical Society,1991,vol. 68,p. 163 - 165
[6]Journal of the Indian Chemical Society,1992,vol. 69,p. 45 - 46
[7]Journal of the Indian Chemical Society,1992,vol. 69,p. 402 - 403
[8]Journal of the Indian Chemical Society,1996,vol. 73,p. 627 - 628
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 514 - 516
[10]Russian Journal of Organic Chemistry,2000,vol. 36,p. 240 - 244
[11]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4726 - 4733
[12]Asian Journal of Chemistry,2012,vol. 24,p. 1223 - 1226
[13]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 7581 - 7587
[14]Phosphorus, Sulfur and Silicon and the Related Elements,2013,vol. 188,p. 989 - 994
[15]Journal of Medicinal Chemistry,2014,vol. 57,p. 2380 - 2392
[16]Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,p. 1337 - 1345
[17]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 183 - 187
[18]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 165 - 170
[19]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 6267 - 6272
[20]British Journal of Pharmacology,2018,vol. 175,p. 2504 - 2519
[21]European Journal of Medicinal Chemistry,2019,vol. 166,p. 167 - 177
[22]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 10489 - 10497
[23]European Journal of Medicinal Chemistry,2020,vol. 185
[24]Russian Journal of Organic Chemistry,2020,vol. 56,p. 802 - 812
    Zh. Org. Khim.,2020,vol. 56,p. 753 - 765,13
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  • [ 122-88-3 ]
  • 9
  • [ 95-57-8 ]
  • [ 79-11-8 ]
  • [ 614-61-9 ]
YieldReaction ConditionsOperation in experiment
65% With potassium hydroxide; In water;Reflux; 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.
General procedure: Equimolar quantities of chloroacetic acid (0.05 mol) and appropriate phenol (6k-s) (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 evaporated in an evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified by adding con. HCl. The precipitated aryloxy acetic acid was filtered and recrystallized from water or ethanol.
With sodium hydroxide; In water; 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
  • 10
  • [ 52094-97-0 ]
  • [ 614-61-9 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; water; at 20℃; for 1h; General procedure: The ester compound (6a-7a & 15a-17a) was dissolved in methanol (30 ml) then subjected to basic hydrolysis with 30% aq. KOH (15ml) in a round-bottomedflask, the resultingmixturewas stirredat roomtemperature for 1 h. After completion of reaction,methanolwas removed under reduced pressure subsequently neutralized with dil.HCl. The resulted white solid was filtered and dried in vacuum produced the respective acid (6b-7b & 15b-17b) in good yields.
With sodium hydroxide; In methanol; at 20℃; for 1h; General procedure: To a stirred solution of 4j (2.5 g, 9.8 mmol) in MeOH (30 mL) was added 3N NaOH solution (13.1 mL, 39.3 mmol). After being stirred at room temperature for 1 h, the mixture was diluted with water (100 mL), acidified with 3N HCl, and extracted with dichloromethane (100 mL × 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title compound (2.12 g, 97% yield) . 1H NMR (300MHz, DMSO-d6) δ 7.49(d, J = 8.8 Hz, 1H), 7.21 (s, 1H), 6.92 (d, J = 8.8 Hz, 1H),4.73 (s, 2H).
With sodium hydroxide; In 1,4-dioxane; at 0 - 20℃; for 1h; General procedure: 1MNaOH was added dropwise to a solution of 21a-g in dioxaneat 0 C. After stirring at r.t. for 1 h, the dioxane was evaporated andthe residue was washed with ethyl acetate. Then the water layerwas acidified with 1M HCl to pH 3 and extracted with ethyl acetate.The combined organic layer was washed with brine (50 mL),dried over anhydrous Na2SO4, and concentrated or directly filteredthe solid to give 22a-g as a white solid.
  • 12
  • [ 614-61-9 ]
  • [ 102-71-6 ]
  • [ 105377-49-9 ]
YieldReaction ConditionsOperation in experiment
95% In ethanol; at 20 - 65℃; General procedure: A solution of tris(2-hydroxyethyl)amine (triethanolamine) and the corresponding acid in ethyl alcohol (molar ratio 1 : 1) was heated for 15-30 min at 65 C and maintained for 1 h at 20-22 C. The mixture was poured into diethyl ether (anhydrous) and maintained for 12 h at 5-10 C. A precipitate was collected by filtration, washed with ether, and dried in vacuo. The products were isolated as colorless powders, well soluble in water and ethanol.
  • 14
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  • [ 4413-45-0 ]
  • [ 137266-08-1 ]
  • 16
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  • [ 614-61-9 ]
  • [ 122-88-3 ]
  • 17
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  • [ 116-02-9 ]
  • [ 58327-07-4 ]
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  • [ 59-46-1 ]
  • [ 54393-09-8 ]
  • 19
  • [ 614-61-9 ]
  • [ 181136-47-0 ]
  • 3-(3-Bromo-4-methoxy-phenyl)-6-(2-chloro-phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole [ No CAS ]
  • 20
  • [ 614-61-9 ]
  • [ 223753-22-8 ]
  • C22H16Cl2N8O2S2 [ No CAS ]
  • 24
  • [ 614-61-9 ]
  • [ 713517-90-9 ]
  • 1-(2-chloro-phenoxy)-5-(2,6-dichloro-benzyl)-9b-phenyl-5,9b-dihydro-1<i>H</i>-2a,5-diaza-benzo[<i>a</i>]cyclobuta[<i>c</i>]cycloheptene-2,4-dione [ No CAS ]
  • 25
  • [ 6956-85-0 ]
  • [ 614-61-9 ]
YieldReaction ConditionsOperation in experiment
95% General procedure: Compound C (0.1 mol), K2CO3 (0.15 mol) and water (50 mL) were added to a 100mL clean eggplant flask. After the reaction mixture was stirred for 5-10 h at 65 ,the reaction mixture was cooled to room temperature and was acidified with aqueous HCl solution (10%) to pH = 2-3. A white solid was afforded by filtration. After vacuum drying, product D was used in the next step. The analytical data corresponded to the literature [9-14].
  • 26
  • [ 614-61-9 ]
  • N-((1R,10S,13R)-5-Amino-tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-yl)-benzenesulfonamide [ No CAS ]
  • N-((1R,10S,13R)-13-Benzenesulfonylamino-tricyclo[8.2.1.03,8]trideca-3,5,7-trien-5-yl)-2-(2-chloro-phenoxy)-acetamide [ No CAS ]
  • 27
  • [ 614-61-9 ]
  • [ 79-19-6 ]
  • [ 84138-74-9 ]
YieldReaction ConditionsOperation in experiment
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.
In trichlorophosphate; for 4h;Reflux; General procedure: A solution of 5j (2.4 g, 11.0 mmol) and thiosemicarbazide (2.0 g, 22.0 mmol) in phosphorus oxychloride (30 mL) was stirred at reflux for 4 h. After cooling,water (50 mL) was added. After being stirred at reflux for 12 h, the mixture was cooled to room temperature and neutralized with 5N NaOH. The resulting solid was separated by filtration, washed with water, and dried in vacuo to give the titlec ompound (2.9 g, 95% yield). 1H NMR (300 MHz, DMSOd6)δ 7.52 (d, J = 9.0 Hz, 1H), 7.36 (s, 1H), 7.03 (d, J = 9.0Hz, 1H), 5.31 (s, 2H).
  • 28
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  • [ 141-75-3 ]
  • [ 27366-24-1 ]
  • 29
  • [ 614-61-9 ]
  • [ 62-53-3 ]
  • polyaniline salt with 2-chlorophenoxyacetic acid; monomer(s): aniline; 2-chlorophenoxyacetic acid [ No CAS ]
  • 30
  • [ 614-61-9 ]
  • potassium; [2-chloro-4-(2-methyl-acryloyl)-phenoxy]-acetate [ No CAS ]
  • 31
  • [ 614-61-9 ]
  • [2-chloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid [ No CAS ]
  • 32
  • [ 95-57-8 ]
  • (+-)-ethylphosphonic acid ethyl ester chloride [ No CAS ]
  • [ 614-61-9 ]
  • 33
  • [ 614-61-9 ]
  • rac-(SR)-(2-chlorophenoxy)-[(5SR)-1-(2,6-dichlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]acetic acid [ No CAS ]
  • 34
  • [ 614-61-9 ]
  • 4-N-(2-chlorophenoxymethyl carboxamido)-3-(pyrazin-2-yl)-1,2,4-triazole-5-thiol [ No CAS ]
  • 35
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  • 36
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  • [ 87657-93-0 ]
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  • [ 87658-20-6 ]
  • 38
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  • [ 86148-99-4 ]
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  • [ 87658-05-7 ]
  • 42
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  • 45
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  • 48
  • [ 614-61-9 ]
  • [ 1009733-85-0 ]
  • [ 1009733-93-0 ]
  • 49
  • [ 614-61-9 ]
  • [ 1023699-54-8 ]
  • [ 1023698-89-6 ]
  • 50
  • [ 614-61-9 ]
  • [ 943138-96-3 ]
  • [ 1023699-12-8 ]
  • 51
  • [ 614-61-9 ]
  • [ 1023699-55-9 ]
  • [ 1023699-25-3 ]
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  • [ 380605-16-3 ]
  • [ 1023699-34-4 ]
  • 53
  • [ 614-61-9 ]
  • [ 62553-49-5 ]
  • [ 1023698-65-8 ]
  • 54
  • [ 614-61-9 ]
  • [ 91971-96-9 ]
  • [ 1023698-77-2 ]
  • 55
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  • [ 21627-59-8 ]
  • [ 1023698-55-6 ]
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  • [ 62552-57-2 ]
  • [ 1023699-00-4 ]
  • 57
  • [ 614-61-9 ]
  • [ 79-19-6 ]
  • [ 119869-02-2 ]
YieldReaction ConditionsOperation in experiment
87% Three coupling reactions were carried out simultaneously on 10 g scale. A solution of 2- chlorophenoxyacetic acid (10 g, 54 mmol), HATU (22.4 g, 59 mmol) and NEt3 (11.1 ml_, 80 mmol) in DMF was stirred at room temperature for 1 hour. Hydrazinecarbothioamide (5.9 g, 64 mmol) was added, and the reaction mixture was stirred at room temperature for two days. After evaporation of the solvent under reduced pressure of the three combined mixtures, the residue was diluted with water and the formed precipitate was filtered and dried to give the title compound as a pale yellow powder (36.6 g, 87%). LC/MS: m/z 260 (M+H)+, Rt: 2.09 min.
87% A solution of 2-chlorophenoxyacetic acid (10 g, 54 mmol), HATU (22.4 g, 59 mmol) and NEt3 (1 1.1 ml_, 80 mmol) in DMF was stirred at room temperature for 1 hour.Hydrazinecarbothioamide (5.9 g, 64 mmol) was added, and the reaction mixture was stirred at room temperature for two days. After evaporation under reduced pressure of the solvent of the three combined mixtures, the residue was diluted with water and the formed precipitate was filtered and dried to give the title compound as a pale yellow powder.Total yield: 36.6 g, 87%.LC/MS: m/z 260 (M+H)+, Rt: 2.09 min.
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  • [ 1000698-88-3 ]
  • [ 931-53-3 ]
  • [ 2043-61-0 ]
  • C33H42ClF2N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.5 mg (34%) To a solution of <strong>[1000698-88-3](2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester</strong> (24.42 mg, 0.10 mmol, 1.0 equiv; Intermediate C) in MeOH (1.0 mL) was added cyclohexanecarbaldehyde (16.83 mg, 18.05 mul, 0.15 mmol, 1.5 equiv; [2043-61-0]) and the mixture stirred at rt. After 30 min, (2-chloro-phenoxy)-acetic acid (18.66 mg, 0.10 mmol, 1.0 equiv; [CAS RN 614-61-9]) and cyclohexyl isocyanide (10.92 mg, 12.27 pi, 0.10 mmol, 1.0 equiv; [931-53-3]) were added and stirring continued at rt for 2 h. A solution of 4 M HCl in dioxane (0.2 mL) was added and the reaction mixture stirred at rt overnight. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile I water provided 17.5 mg (34%) of the title compound. MS (ISP): 516.2 [M+H]+.
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  • [ 931-53-3 ]
  • [ 2043-61-0 ]
  • C33H43ClFN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of (2-amino-5-fluoro-phenyl)-carbamic acid tert-butyl ester (22.63 mg, 0.10 mmol, 1.0 equiv, Intermediate B) in MeOH (1.0 mL) was added cyclohexanecarbaldehyde (16.83 mg, 18.05 μl 0.15 mmol, 1.5 equiv; [2043-61-0]) and the mixture stirred at rt. After 30 min, (2-chloro-phenoxy)-acetic acid (18.66 mg, 0.10 mmol, 1.0 equiv; [CAS RN 614-61-9]) and cyclohexyl isocyanide (10.92 mg, 12.27 μl, 0.10 mmol, 1.0 equiv; [931-53-3]) were added and stirring continued at rt for 2 h. A solution of 4 M HCl in dioxane (0.2 mL) was added and the reaction mixture stirred at rt overnight. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 6.3 mg (13%) of the title compound. MS (ISP): 498.1 [M+H]+.
  • 60
  • [ 614-61-9 ]
  • [ 38538-07-7 ]
  • [ 1107603-61-1 ]
  • [ 1107603-62-2 ]
  • 61
  • [ 94-75-7 ]
  • [ 614-61-9 ]
  • [ 122-88-3 ]
  • 62
  • [ 94-75-7 ]
  • [ 614-61-9 ]
  • [ 122-88-3 ]
  • [ 120-83-2 ]
  • 63
  • [ 95-57-8 ]
  • [ 3926-62-3 ]
  • [ 614-61-9 ]
  • 64
  • [ 614-61-9 ]
  • [ 622-52-6 ]
  • [ 1392217-15-0 ]
  • 65
  • [ 614-61-9 ]
  • [ 103-85-5 ]
  • [ 1392217-10-5 ]
  • 66
  • [ 614-61-9 ]
  • [ 3696-23-9 ]
  • [ 1392217-21-8 ]
  • 67
  • [ 614-61-9 ]
  • [ 123-30-8 ]
  • [ 1225506-03-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: A 50 ml round-bottomed flask was charged with a magnetic stirrer, dry benzene (10 ml), acid compound (6b-7b & 15b-17b) and thionyl chloride (1.0 ml). The reaction mixture was refluxed for 2 h, after completion of required time remove the solvent and excess SOCl2 under reduced pressure. This acid chloride was again dissolved in dry benzene (10 ml) followed by addition of 4-hydroxy aniline in excess, the resulted mixture was refluxed until the acid chloride had been completely consumed as judged by TLC. After completion of reaction the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel with MeOH/CH3Cl (0.5:9.5) to afford 4-hydroxy amides (6c-7c & 15c-17c) in good yields.
  • 68
  • [ 614-61-9 ]
  • [ 2381-75-1 ]
  • [ 944701-13-7 ]
  • 69
  • [ 614-61-9 ]
  • tert-butyl (1R,5S)-7-(1H-imidazole-1-carbonyl)-3,7-diazabicyclo[3.3.1]nonan-3-carboxylate [ No CAS ]
  • C20H27ClN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% General procedure: Methyl iodide (570 mg, 4 mmol) was added to a stirred solution of 12 (320 mg, 1 mmol) dissolved in dry MeCN (2 mL) and dry THF (2 mL) at rt. The volatiles were removed under reduced pressure after 24 h, the residue was dissolved in dry MeCN (4 mL), and Et3N (101 mg, 1 mmol) and the appropriate carboxylic acid (1 mmol) were added. The solution was allowed to stir at rt for 12-120 h before the volatiles were removed under reduced pressure. The residue was purified by flash chromatography (silica gel, mixtures of CH2Cl2 and MeOH-40:1, 20:1 or 9:1).
  • 70
  • [ 614-61-9 ]
  • [ 95-02-3 ]
  • [ 1610784-98-9 ]
YieldReaction ConditionsOperation in experiment
65% General procedure: To a solution of corresponding substituted phenoxyacetic acid 3 or 5 (1.5 mmol) and Et3N (0.16 g, 1.6 mmol) in THF (15 mL) was added ethyl chlorocarbonate (0.17g, 1.6 mmol) in THF (2 mL) slowly at -5C. After the addition was complete, the cold mixture was stirred for an additional 15 min. A solution of 2 (0.22 g, 1.6 mmol) in DMF (2 mL) was added dropwise while the temperature was kept at -5C. After the addition was complete, the mixture was stirred at room temperature for 12 h. It was poured into water (30mL), and the precipitate was collected by filtration and dried in the atmospheric pressure. Recrystallization with appropriate solvent afforded the desired solid compounds 6a-6n. 5.3.9 N-((4-Amino-2-methylpyrimidin-5-yl)methyl)-2-(2-chlorophenoxy)acetamide (6i) White solid, yield: 65%, mp 188-190; 1H NMR (CDCl3, 400 MHz): δ 2.47 (s, 3H, CH3), 4.38 (d, 2H, J = 9.6 Hz, CH2), 4.50 (s, 2H, CH2), 5.92 (s, 2H, NH2), 6.83 (d, 2H, J = 4.4 Hz, Ar-H), 7.07 (s, 1H, NH), 7.26 (t, 2H, J = 4.0 Hz, Ar-H), 7.98 (s, 1H, CH); 13C NMR (DMSO-d6, 100 MHz): δ 25.18, 36.48, 67.16, 110.65, 116.62, 125.14, 129.34, 154.89, 156.49, 161.58, 165.78, 168.46. EI-MS m/z (%): 308.2 (M++2, 6.53), 306.2 (M+, 22.59). Anal. Calcd for C14H15ClN4O2: C, 54.82; H, 4.93; N, 18.26. Found: C, 54.57; H, 5.28; N, 18.35.
  • 71
  • [ 614-61-9 ]
  • [ 934-32-7 ]
  • [ 107249-99-0 ]
YieldReaction ConditionsOperation in experiment
38% 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.
  • 72
  • [ 614-61-9 ]
  • [ 2963-77-1 ]
  • [ 364620-23-5 ]
YieldReaction ConditionsOperation in experiment
55% 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.
  • 73
  • [ 614-61-9 ]
  • [ 33509-43-2 ]
  • [ 1621091-20-0 ]
YieldReaction ConditionsOperation in experiment
74% With trichlorophosphate; at 90℃; for 8h; General procedure: An equimolar mixtures of 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazine-5(H)-one (0.01mol) (3) and substituted aryloxyacetic acids (0.01mol) (4) were condensed in presence of POCl3 at 90C, for 8h. The reactions were carried out in dry condition. The reaction mixtures were cooled and poured into crushed ice drop wise with vigorous shaking, yielded solid product, filtered and recrystallized from ethanol to afford analytical samples (5a-5n) (Scheme 2).
  • 74
  • [ 94-75-7 ]
  • [ 614-61-9 ]
  • [ 122-59-8 ]
YieldReaction ConditionsOperation in experiment
With 0.5% Pd/Sibunit carbon material; hydrogen; In water; at 30℃; under 760.051 Torr; for 100h; General procedure: Two replicates of each hydrodechlorination run were carriedout in a continuous basket stirred tank reactor (Carberry SpinningCatalyst Basket) from Autoclave Engineers, provided with tem-perature, pressure and gas flow control. The aqueous solution ofeach organochlorinated reactant was fed to the reactor at 4 mL/minand H2was continuously passed at 50 N mL/min. A catalyst load-ing of 2.95 g/L was always used, so that the space-time was fixedat 2.95 kgcath/molCl.All the experiments were performed at 30C,atmospheric pressure and 600 rpm stirring velocity. The progressof the reaction was followed by analyzing periodically samplesof the exit liquid stream taken with a fraction collector (FC203B-Gilson) along the 100 h on stream of the experiments. The datareproducibility was better than ±5%. The existence of internal andexternal mass transfer limitations is discarded in our experimentalconditions, as demonstrated in previous studies [30,31]. The organic compounds in the effluent from HDC of 2,4-DCPwere analyzed by GC with a flame ionization detector (GC 3900 Var-ian) using a 30 m long × 0.25 mm i.d. capillary column (CP-Wax 52CB). 2,4-D, MCPA and the aromatic reaction byproducts were quan-tified by HPLC (Varian Prostar 325) with a UV detector using a C18as stationary phase (Valco Microsorb-MW 100-5 C18) at 280 nmand a mixture of acetonitrile and acid water (acetic acid 0.1%) asmobile phase at 0.5 mL/min. Analysis of chloride was performedby ionic chromatography (Metrohm 790 Personal IC). The pH wasmeasured with a pH meter (CRISON) Ecotoxicity measurements were carried out by a bioassay fol-lowing the standard Microtox test procedure (ISO 11348-3, 1998),based on the decrease of light emission by the marine bacteria Vib-rio fischeri (Photobacterium phosphoreum), using a Microtox M500Analyzer (Azur Environmental), in order to determine of EC50val-ues of the reaction compounds.
With hydrogen; In water; at 30℃; under 760.051 Torr; Two replicates of each hydrodechlorination run were carried out in a continuous basket stirred tank reactor (Carberry SpinningCatalyst Basket) from Autoclave Engineers, provided with temperature, pressure and gas flow control. The aqueous solution of each organochlorinated reactant was fed to the reactor at 4 mL/minand H2 was continuously passed at 50 N mL/min. A catalyst loading of 2.95 g/L was always used, so that the space-time was fixedat 2.95 kgcath/molCl. All the experiments were performed at 30C, atmospheric pressure and 600 rpm stirring velocity. The progress of the reaction was followed by analyzing periodically samples of the exit liquid stream taken with a fraction collector (FC203B-Gilson) along the 100 h on stream of the experiments. The data reproducibility was better than ±5%.
  • 75
  • [ 93-76-5 ]
  • [ 614-61-9 ]
  • [ 94-75-7 ]
  • [ 582-54-7 ]
  • [ 122-59-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; sodium hydroxide at 25℃; Inert atmosphere;
  • 76
  • [ 614-61-9 ]
  • [ 107-21-1 ]
  • 2-hydroxyethyl 2-(2-chlorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With iodine; In toluene;Reflux; General procedure: A mixture of phenoxy carboxylic acid 1 (2 mmol), ethylene glycol (10 mmol), I2 (0.025g, 0.1 mmol) in toluene (10 mL) was heated under reflux for 2-3 h. When the reaction was completed (TLC), the mixture was washed with 10% Na2S2O3 (10 mL × 3) and H2O (10 mL × 2). The organic layer was dried over anhydrous Na2SO4. The crude was purified by column chromatography to afford the desired products 3a-3p.
  • 77
  • [ 614-61-9 ]
  • [ 111-46-6 ]
  • 2-(2-hydroxyethoxy)ethyl 2-(2-chlorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With iodine; In toluene;Reflux; General procedure: A mixture of phenoxy carboxylic acid 1 (2 mmol), ethylene glycol (10 mmol), I2 (0.025g, 0.1 mmol) in toluene (10 mL) was heated under reflux for 2-3 h. When the reaction was completed (TLC), the mixture was washed with 10% Na2S2O3 (10 mL × 3) and H2O (10 mL × 2). The organic layer was dried over anhydrous Na2SO4. The crude was purified by column chromatography to afford the desired products 3a-3p.
  • 78
  • [ 614-61-9 ]
  • [ 112-27-6 ]
  • 2-(2-(2-hydroxyethoxy)ethoxy)ethyl 2-(2-chlorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With iodine; In toluene;Reflux; General procedure: A mixture of phenoxy carboxylic acid 1 (2 mmol), ethylene glycol (10 mmol), I2 (0.025g, 0.1 mmol) in toluene (10 mL) was heated under reflux for 2-3 h. When the reaction was completed (TLC), the mixture was washed with 10% Na2S2O3 (10 mL × 3) and H2O (10 mL × 2). The organic layer was dried over anhydrous Na2SO4. The crude was purified by column chromatography to afford the desired products 3a-3p.
  • 79
  • [ 614-61-9 ]
  • [ 112-60-7 ]
  • 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 2-(2-chlorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With iodine; In toluene;Reflux; General procedure: A mixture of phenoxy carboxylic acid 1 (2 mmol), ethylene glycol (10 mmol), I2 (0.025g, 0.1 mmol) in toluene (10 mL) was heated under reflux for 2-3 h. When the reaction was completed (TLC), the mixture was washed with 10% Na2S2O3 (10 mL × 3) and H2O (10 mL × 2). The organic layer was dried over anhydrous Na2SO4. The crude was purified by column chromatography to afford the desired products 3a-3p.
  • 80
  • Sodium; (2-chloro-phenoxy)-acetate [ No CAS ]
  • [ 614-61-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water;pH 1; 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. 2-Chlorophenoxyacetic acid (1f) Following the general procedure the compound 1f was obtained in 69 % yield as a white solid. m.p. 151-153 C. 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J= 7.9 Hz, 1H), 7.28-7.18 (m, 1H), 6.99 (t, J = 7.7 Hz, 1H), 6.89 (d,J = 8.2 Hz, 1H), 4.75 (s, 2H). MS (ESI) m/z: 185 [M-H]-.(S4)
  • 82
  • [ 614-61-9 ]
  • Mg(2-chlorophenoxyacetate)<SUB>2</SUB>(H<SUB>2</SUB>O)<SUB>4</SUB> [ No CAS ]
  • 83
  • [ 614-61-9 ]
  • [ 59084-06-9 ]
  • 2-(2-chlorophenoxy)-1-(4-(2-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% General procedure: Thirty-three nitro-containing analogs of GRI392104 (Table 1)were synthesized using a two-step reaction (Scheme 2). To a dryround bottom flask, 190 lmol of carboxylic acid building block,190 lmol of HBTU (O-(benzotriazol-1-yl)-N,N,N0 ,N0-tetramethyluroniumhexafluorophosphate) and 190 lmol of N,N-diisopropylethylamine(DIPEA) were combined in 1 mL of N,Ndimethylformamide(DMF) and stirred for 5 min at room temperature.After the solid carboxylic acid had dissolved and the clearsolution turned amber, 97 lmol of amine building block was dissolvedin 1 mL of DMF and added to the reaction flask. All reactionswere complete within 20 min, as confirmed by analytical thin layerchromatography (TLC) in 60:40 ethyl acetate/hexanes. The resultingamide products were extracted into chloroform and washedwith water (twice), sodium bicarbonate (once), and water again(three times). The organic layers were dried and 1H NMR (in CDCl3)was used to ensure product formation. Individual products (as yellowsolids) were isolated using preparative TLC with a mobilephase of 60:40 ethyl acetate/hexanes followed by extraction fromscraped silica using 50:50 ethyl acetate/methylene chloride. Purityfor all thirty-three compounds was confirmed by 1H NMR, 13C NMRand LC-MS. High resolution MS data for all previously unreportedcompounds gave the expected mass values with absolute errorsranging from 0.5 to 13.9 ppm.
  • 84
  • [ 614-61-9 ]
  • [ 54054-85-2 ]
  • 2-(2-chlorophenoxy)-1-(4-(3-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% General procedure: Thirty-three nitro-containing analogs of GRI392104 (Table 1)were synthesized using a two-step reaction (Scheme 2). To a dryround bottom flask, 190 lmol of carboxylic acid building block,190 lmol of HBTU (O-(benzotriazol-1-yl)-N,N,N0 ,N0-tetramethyluroniumhexafluorophosphate) and 190 lmol of N,N-diisopropylethylamine(DIPEA) were combined in 1 mL of N,Ndimethylformamide(DMF) and stirred for 5 min at room temperature.After the solid carboxylic acid had dissolved and the clearsolution turned amber, 97 lmol of amine building block was dissolvedin 1 mL of DMF and added to the reaction flask. All reactionswere complete within 20 min, as confirmed by analytical thin layerchromatography (TLC) in 60:40 ethyl acetate/hexanes. The resultingamide products were extracted into chloroform and washedwith water (twice), sodium bicarbonate (once), and water again(three times). The organic layers were dried and 1H NMR (in CDCl3)was used to ensure product formation. Individual products (as yellowsolids) were isolated using preparative TLC with a mobilephase of 60:40 ethyl acetate/hexanes followed by extraction fromscraped silica using 50:50 ethyl acetate/methylene chloride. Purityfor all thirty-three compounds was confirmed by 1H NMR, 13C NMRand LC-MS. High resolution MS data for all previously unreportedcompounds gave the expected mass values with absolute errorsranging from 0.5 to 13.9 ppm.
  • 85
  • [ 614-61-9 ]
  • [ 6269-89-2 ]
  • 2-(2-chlorophenoxy)-1-(4-(4-nitrophenyl)piperazin-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% General procedure: Thirty-three nitro-containing analogs of GRI392104 (Table 1)were synthesized using a two-step reaction (Scheme 2). To a dryround bottom flask, 190 lmol of carboxylic acid building block,190 lmol of HBTU (O-(benzotriazol-1-yl)-N,N,N0 ,N0-tetramethyluroniumhexafluorophosphate) and 190 lmol of N,N-diisopropylethylamine(DIPEA) were combined in 1 mL of N,Ndimethylformamide(DMF) and stirred for 5 min at room temperature.After the solid carboxylic acid had dissolved and the clearsolution turned amber, 97 lmol of amine building block was dissolvedin 1 mL of DMF and added to the reaction flask. All reactionswere complete within 20 min, as confirmed by analytical thin layerchromatography (TLC) in 60:40 ethyl acetate/hexanes. The resultingamide products were extracted into chloroform and washedwith water (twice), sodium bicarbonate (once), and water again(three times). The organic layers were dried and 1H NMR (in CDCl3)was used to ensure product formation. Individual products (as yellowsolids) were isolated using preparative TLC with a mobilephase of 60:40 ethyl acetate/hexanes followed by extraction fromscraped silica using 50:50 ethyl acetate/methylene chloride. Purityfor all thirty-three compounds was confirmed by 1H NMR, 13C NMRand LC-MS. High resolution MS data for all previously unreportedcompounds gave the expected mass values with absolute errorsranging from 0.5 to 13.9 ppm.
  • 86
  • [ 614-61-9 ]
  • [ 446831-27-2 ]
  • 2-(4-(2-(2-chlorophenoxy)acetyl)piperazin-1-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% General procedure: Twenty-two carboxy-containing analogs of GRI392104 (Table 1)were synthesized using a two-step reaction (Scheme 2). To a dryround bottom flask, 140 lmol of 2-phenoxyacetic acid buildingblock, 126 lmol of HBTU, and 140 lmol DIPEA were combined in4 mL of dichloromethane (DCM) and sonicated for 5 min beforetransferring 140 lmol of ortho- or meta-carboxy amine buildingblock into the reaction flask with an additional 1 mL of DCM. Thiswas sonicated for 60 min and tracked with analytical TLC in either95:5 ethyl acetate/methanol (ortho compounds) or 90:10 chloroform/methanol (meta compounds). Products were then extractedinto DCM and washed with additional water three times beforedrying the organic layer over sodium sulfate and filtering into atared flask and drying to a white crude powder to confirm synthesisvia 1H NMR (in CDCl3). Once synthesis was confirmed, crudeproduct was mixed with silica and additional chloroform beforedrying the resulting slurry in vacuo and utilizing flash chromatographyto purify the compounds over a 10 g Biotage SNAP column at25 mL/min unless otherwise mentioned (eluents were the samefrom analytical TLC). Purity was confirmed by 1H NMR before dryingthe products to a solid white residue (Supplemental Fig. 1). 13CNMR data was collected for all previously unreported compounds(Supplemental Fig. 2). High resolution MS data for all previouslyunreported compounds gave the expected mass values with absoluteerrors ranging from 0.0 to 20.3 ppm. They were then diluted to3 mM in DMSO for activity analysis.
  • 87
  • [ 614-61-9 ]
  • [ 446831-28-3 ]
  • 3-(4-(2-(2-chlorophenoxy)acetyl)piperazin-1-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% General procedure: Twenty-two carboxy-containing analogs of GRI392104 (Table 1)were synthesized using a two-step reaction (Scheme 2). To a dryround bottom flask, 140 lmol of 2-phenoxyacetic acid buildingblock, 126 lmol of HBTU, and 140 lmol DIPEA were combined in4 mL of dichloromethane (DCM) and sonicated for 5 min beforetransferring 140 lmol of ortho- or meta-carboxy amine buildingblock into the reaction flask with an additional 1 mL of DCM. Thiswas sonicated for 60 min and tracked with analytical TLC in either95:5 ethyl acetate/methanol (ortho compounds) or 90:10 chloroform/methanol (meta compounds). Products were then extractedinto DCM and washed with additional water three times beforedrying the organic layer over sodium sulfate and filtering into atared flask and drying to a white crude powder to confirm synthesisvia 1H NMR (in CDCl3). Once synthesis was confirmed, crudeproduct was mixed with silica and additional chloroform beforedrying the resulting slurry in vacuo and utilizing flash chromatographyto purify the compounds over a 10 g Biotage SNAP column at25 mL/min unless otherwise mentioned (eluents were the samefrom analytical TLC). Purity was confirmed by 1H NMR before dryingthe products to a solid white residue (Supplemental Fig. 1). 13CNMR data was collected for all previously unreported compounds(Supplemental Fig. 2). High resolution MS data for all previouslyunreported compounds gave the expected mass values with absoluteerrors ranging from 0.0 to 20.3 ppm. They were then diluted to3 mM in DMSO for activity analysis.
  • 88
  • [ 614-61-9 ]
  • [ 85474-75-5 ]
  • 4-(4-(2-(2-chlorophenoxy)acetyl)piperazin-1-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% General procedure: For the remaining eleven para-substituted carboxy-containinganalogs of GRI392104 (Table 1), the same reagents were combinedin a clean, dry flask in 1 mL dimethyl sulfoxide (DMSO). After 5 minof stirring, the clear solution turned amber and 140 lmol of solidpara-carboxy amine building block was dissolved into the reactionmixture. Over the course of an hour, the amber solution slowly turned cloudy white. The reactions were worked up in the samemanner as the other twenty-two carboxy analogs, except ethylacetate was used instead of methylene chloride before synthesiswas confirmed with 1H NMR. Products were then purified over10 g Biotage SNAP columns at 25 mL/min (method C) or via preparativeTLC in 92.5:7.5 chloroform/methanol (method D). Productsfrom method D were extracted in 50:50 ethyl acetate/methylenechloride and dried to a solid white residue. Purity was confirmedvia 1H NMR before drying the products to a solid white powder(Supplemental Fig. 1). 13C NMR data was collected for all previouslyunreported compounds (Supplemental Fig. 2). High resolution MSdata for all previously unreported compounds gave the expectedmass values with absolute errors ranging from 0.0 to 20.3 ppm.Compounds were stored at 3 mM in DMSO for activity analysis.
  • 89
  • [ 614-61-9 ]
  • [ 504-02-9 ]
  • C14H13ClO4 [ No CAS ]
  • 90
  • [ 614-61-9 ]
  • [ 126-81-8 ]
  • C16H17ClO4 [ No CAS ]
  • 91
  • [ 95-57-8 ]
  • [ 105-36-2 ]
  • [ 614-61-9 ]
  • 92
  • [ 614-61-9 ]
  • [ 818-08-6 ]
  • C64H96Cl4O14Sn4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.2% In benzene; for 18h;Inert atmosphere; Reflux; A 500 mL three-necked flask with nitrogen gas was charged with 3.720 g (20.0 mmol) of <strong>[614-61-9]o-chlorophenoxyacetic acid</strong>, 5.704 g (23.0 mmol) of dibutyltin oxide and 300 mL of anhydrous benzene, stirred and refluxed for 18 h,After the completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was evaporated to dryness by rotary evaporator under the conditions of a pressure of 0.009 MPa and a temperature of 45 C to obtain a white solid which was recrystallized from a mixed solvent of dichloromethane and methanol,Wherein the volume ratio of dichloromethane to methanol is 1: 6, under the condition of 15-35 DEG C, the solvent is controlled to volatilize and crystallize to obtain colorless and transparent crystal, which is the n-butyltin phenoxyacetate of the invention. Yield: 54.2%.
  • 93
  • [ 614-61-9 ]
  • N-(6-(3-aminopiperdin-1-yl)-5-phenylpyrimidin-4-yl)acetamide [ No CAS ]
  • N-(1-(6-acetamido-5-phenylpyrimidin-4-yl)piperidin-3-yl)-2-(2-chlorophenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 0 - 20℃; for 18h; Propylphoshonic anhydride (T3P) solution (≥50wt % in 52 EtOAc, (0.2mL, 0.674mmol) was added to a solution of 6j 82 2-(2-chlorophenoxy) acetic acid (0.059g, 0.321mmol), 16 5 (0.100g, 0.321mmol) and 21 Et3N (0.081g, 0.802mmol) in 49 CH2Cl2 (10mL) at 0C. The reaction was allowed to warm to room temperature overnight. The mixture was subsequently diluted with CH2Cl2, and the organic layer was sequentially washed with saturated aqueous NaHCO3 and aqueous 2M HCl and finally dried over Na2SO4. Purification by flash chromatography (CH2Cl2/MeOH) yielded 83 16 (71mg, 83%) as a white solid; 1H NMR (500MHz, DMSO-d6) δ (ppm) 8.88 (s, 1H), 8.23 (s, 1H), 7.92 (d, J=7.2Hz, 1H), 7.49 (t, J=7.6Hz, 2H), 7.40 (m, 1H), 7.32-7.28 (m, 3H), 7.01 (s, 2H), 6.92-6.87 (m, 1H), 4.49 (s, 2H), 3.71 (m, 2H), 3.30 (m, 1H), 2.89 (m, 1H), 2.66 (m, 1H), 1.90 (s, 3H), 1.69 (m, 1H), 1.42 (m, 2H);13C NMR (126MHz, DMSO-d6) δ (ppm) 171.42, 168.73, 165.96, 162, 159.35, 157.95, 156.52, 150.37, 149.77, 138, 133.97, 133.00, 132.74, 130.17, 129.10, 128.39, 128.16, 127.55, 120.47, 120.02, 114.28, 112.88, 97.78, 66.33, 50.21, 47.00, 45.13, 44.54, 28.64, 21.94, 20.32, 7.88;
  • 94
  • [ 36304-23-1 ]
  • [ 614-61-9 ]
YieldReaction ConditionsOperation in experiment
99% With trifluoroacetic acid; In N,N-dimethyl-formamide; at 20℃; for 1.5h; The ester 1 (22.7mmol; 5.50g) was dissolved in trifluoroacetic acid (22.7mL) and stirred at RT for 1h and a half until the reaction was complete. The crude was concentrated under reduced pressure. The obtained solid was taken back with DCM several times then evaporated to dryness to afford a white solid (4.20g; 99%), which was used without further treatment. 1H NMR (300MHz, DMSO) δ 13.10 (s, 1H), 7.43 (dd, J=7.9, 1.6Hz, 1H), 7.27 (ddd, J=8.5, 7.5, 1.6Hz, 1H), 7.06-6.92 (m, 2H), 4.80 (s, 2H).
  • 95
  • [ 614-61-9 ]
  • [ 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 (2-chlorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20℃; 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%).
  • 96
  • [ 614-61-9 ]
  • holmium(III) chloride hexahydrate [ No CAS ]
  • 3C8H6ClO3(1-)*2H2O*Ho(3+) [ No CAS ]
  • 97
  • [ 614-61-9 ]
  • dysprosium(III) chloride hexahydrate [ No CAS ]
  • 3C8H6ClO3(1-)*Dy(3+)*2H2O [ No CAS ]
  • 98
  • [ 614-61-9 ]
  • 3C8H6ClO3(1-)*Sr(2+)*4H2O [ No CAS ]
  • 99
  • [ 614-61-9 ]
  • 2C8H6ClO3(1-)*Ba(2+)*2H2O [ No CAS ]
  • 100
  • [ 67-56-1 ]
  • [ 614-61-9 ]
  • methyl [2-chloro-4-(chlorosulfonyl)phenoxy]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Formation of (4-{bis[(2,4-dimethoxyphenyl)methyl]sulfamoyl}-2-chlorophenoxy)acetic acid 8 (0064) 2-Chlorophenoxyacetic acid (2.31 g, 12. 4 mmol) was dissolved in methanol, and 3 ml of acetyl chloride was added dropwise. The mixture was allowed to stir overnight, then the methanol was removed under vacuum, and the residue dissolved in DCM and washed with saturated sodium bicarbonate. The material was then used in the next step, which involved treating with 8.0 ml (0.124 mol) of chlorosulfonic acid which was added dropwise to the neat ester at 0 C., and then allowed to stir overnight while gradually warming to room temperature. The homogenous mixture was then diluted with DCM and then poured onto ice. The resulting layers were separated, and the aqueous extracted with DCM. The combined organics were washed with brine, dried over sodium sulfate, the solution was filtered and then concentrated to give 3.2 g (86%) of purplish crystalline solid [2-chloro-4-(chlorosulfonyl)phenoxy]acetic acid, methyl ester 6. 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=2.7 Hz, 1H), 7.91 (dd, J=9.0, 2.4 Hz, 1H), 6.95 (d, J=9.0 Hz, 1H), 4.87 (s, 2H), 3.86 (s, 3H). This material was then placed in a round bottom flask, suspended in DCM (20 ml) and chilled to 0 C. 3.37 g (10.7 mmol) of Bis(2,4-Dimethoxybenzyl)amine (prepared as described in Organic and Biomolecular Chemistry, 10(37), 7610-7617, 2012) and TEA (3.0 ml, 21.4 mmol) were dissolved in DCM (30 ml) and added dropwise to the halide solution. The mixture was then allowed to gradually warm to room temperature while stirring overnight. The next day the mixture was evaporated onto silica and subjected to flash chromatography using a 0 to 10% gradient of EtOAc in DCM to obtain 5.79 g (93%) of the intermediate methyl (4-{bis[(2,4-dimethoxyphenyl)methyl]sulfamoyl}-2-chlorophenoxy)acetate 7 as a semi-crystalline solid 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=2.1 Hz, 1H), 7.47 (dd, J=8.7 Hz, 1H), 7.19 (d, J=8.4 Hz, 2H), 6.71 (d, J=8.7 Hz, 1H), 6.42 (dd, J=8.4, 2.4 Hz, 2H), 6.29 (d, J=2.1 Hz, 2H), 4.76 (s, 2H), 4.39 (s, 4H), 3.84 (s, 3H), 3.80 (s, 6H), 3.65 (s, 6H). The methyl ester was saponified by treating with 10 ml of 5M LiOH-H2O in 100 ml THF to afford acid 8 (5.65 g, 99%).
  • 101
  • [ 462-08-8 ]
  • [ 614-61-9 ]
  • [ 25288-47-5 ]
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