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Chemical Structure| 874-60-2 Chemical Structure| 874-60-2
Chemical Structure| 874-60-2

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Product Citations

Product Citations

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega ; Raja Dey ; Katherine A. Hicks ; Sumitha Rao , et al.

Abstract: The suppressor of T cell receptor signaling (Sts) proteins are negative regulators of immune signaling. Genetic inactivation of these proteins leads to significant resistance to infection. From a 590,000 compound high-throughput screen, we identified the 2-(1H)-quinolinone derivative, , as a putative inhibitor of Sts activity. , and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the , the acid, and the moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the . Although has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

Alternative Products

Product Details of p-Toluoyl chloride

CAS No. :874-60-2
Formula : C8H7ClO
M.W : 154.59
SMILES Code : O=C(Cl)C1=CC=C(C)C=C1
MDL No. :MFCD00000696
InChI Key :NQUVCRCCRXRJCK-UHFFFAOYSA-N
Pubchem ID :13405

Safety of p-Toluoyl chloride

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of p-Toluoyl chloride

* 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 [ 874-60-2 ]

[ 874-60-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 38993-84-9 ]
  • [ 874-60-2 ]
  • [ 158629-17-5 ]
  • 2
  • [ 700-46-9 ]
  • [ 7677-24-9 ]
  • [ 874-60-2 ]
  • [ 109271-55-8 ]
  • 3
  • [ 103766-25-2 ]
  • [ 874-60-2 ]
  • 4-Methyl-benzoic acid 5-chloro-2-oxo-1,2-dihydro-pyridin-4-yl ester [ No CAS ]
  • C21H16ClNO4 [ No CAS ]
  • 4
  • [ 103766-25-2 ]
  • [ 874-60-2 ]
  • C21H16ClNO4 [ No CAS ]
  • 5
  • [ 6995-79-5 ]
  • [ 874-60-2 ]
  • trans-1,4-bis-(4-methylbenzoyloxy)-cyclohexane [ No CAS ]
  • 6
  • [ 88088-95-3 ]
  • [ 874-60-2 ]
  • [ 130749-20-1 ]
  • 7
  • [ 462-06-6 ]
  • [ 874-60-2 ]
  • [ 530-46-1 ]
  • 8
  • [ 40963-14-2 ]
  • [ 874-60-2 ]
  • [ 100594-41-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; water; EXAMPLE 16 Preparation of N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide STR62 A stirred mixture containing 13.0 g (0.10 mol) of <strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> and 15.3 mL (0.11 mol) of triethylamine in 150 mL of dry THF is treated dropwise at 5 to 10 C. with a solution of 15.5 g (0.10 mol) of p-toluoyl chloride in 25 mL dry THF. After being allowed to warm to ambient temperatures over a 16 hour period, the reaction mixture is treated with 50 mL water and stirred for one hour. The resulting three phases are filtered; the filtrate is separated and the aqueous phase is extracted with 150 mL ethyl acetate. All organic phases are combined, washed with 100 mL of a saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. A white solid residue is obtained which weighs 17.3 g, mp 145-152 C. The nmr spectrum is consistent with the desired structure.
With triethylamine; In tetrahydrofuran; water; EXAMPLE 16 Preparation of N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide STR27 A stirred mmixture containing 13.0 g (0.10 mol) of <strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> and 15.3 mL (0.11 mole) of triethylamine in 150 mL of dry THF is treated dropwise at 5 to 10 C. with a solution of 15.5 g (0.10 mol) of p-toluoyl chloride in 25 mL dry THF. After being allowed to warm to ambient temperatures over a 16 hour period, the reaction mixture is treated with 50 mL water and stirred for one hour. The resulting three phases are filtered; the filtrate is separated and the aqueous phase is extracted with 150 mL ethyl acetate. All organic phases are combined, washed with 100 mL of a saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. A white solid residue is obtained which weighs 17.3 g, mp 145-152 C. The nmr spectrum is consistent with the desired structure.
With triethylamine; In acetone; EXAMPLE 10 (Reference) Preparation of (+-)-N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide To a stirred solution containing 10.0 g (0.077 mol) of (+-)-<strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> and 12 ml triethylamine in 125 ml acetone is added, dropwise, 11.9 g (0.077 mol) p -toluoyl chloride. After the addition, the mixture is stirred a further hour at room temperature. Then the mixture is poured into 300 ml water with stirring. The white solid is removed by filtration, washed with water and air dried to give 15.8 g product mp 154-159C. This is recrystallized from acetonitrile to give 11.6 g of analytically pure (+-)-N-(1-carbamoyl-1,2-dimethyl-propyl)- p -toluamide mp 160-162C. When the reaction is repeated using the (+)-<strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> rather than the (+-)-<strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong>, the corresponding (-)-N-(1-carbamoyl-1,2-dimethylpropyl)- p -toluamide is obtained, mp 138-140C, [alpha] [25/D ] = -57.18 (C = 0.0288 g/ml THF).
  • 9
  • [ 6414-69-3 ]
  • [ 874-60-2 ]
  • [ 6942-61-6 ]
  • 10
  • [ 874-60-2 ]
  • [ 28992-50-9 ]
  • resin-bound 1-benzyl-2-methoxyethylamine [ No CAS ]
  • <i>N</i>-(1-methoxymethyl-2-phenyl-ethyl)-4-methyl-benzamide [ No CAS ]
  • (1-methoxymethyl-2-phenyl-ethyl)-(5-<i>p</i>-tolyl-[1,2,4]oxadiazol-3-yl)-amine [ No CAS ]
  • 11
  • [ 874-60-2 ]
  • [ 28992-50-9 ]
  • resin-bound 3-methoxy-1-propylamine [ No CAS ]
  • (3-methoxy-propyl)-(5-<i>p</i>-tolyl-[1,2,4]oxadiazol-3-yl)-amine [ No CAS ]
  • 12
  • [ 874-60-2 ]
  • [ 28992-50-9 ]
  • resin-bound 3-pentylamine [ No CAS ]
  • (1-ethyl-propyl)-(5-<i>p</i>-tolyl-[1,2,4]oxadiazol-3-yl)-amine [ No CAS ]
  • 13
  • [ 40230-24-8 ]
  • [ 874-60-2 ]
  • <i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-4-methyl-benzamide [ No CAS ]
  • 14
  • [ 21109-25-1 ]
  • [ 874-60-2 ]
  • [ 943188-11-2 ]
  • 15
  • [ 874-60-2 ]
  • [ 101078-51-7 ]
  • 16
  • [ 34715-64-5 ]
  • [ 874-60-2 ]
  • [ 2456-81-7 ]
  • 3,4-bis(p-toluyloxy)phenyl N-(tert-butyl)aminomethyl ketone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tributyl-amine; In acetonitrile; EXAMPLE 7 To a stirred suspension of 26.0 g (0.10 mole) of 3,4-dihydroxyphenyl N-(tert-butyl)aminomethyl ketone hydrochloride in 260 ml of acetonitrile was added 38.7 g (0.209 mole) of tributylamine, followed after 10 minutes by 600 mg of 4-(1-pyrrolidinyl)pyridine. To this mixture was added 33 g (0.213 mole) of p-toluyl chloride dropwise over a 20 minute period. The reaction mixture was allowed to stand at room temperature and the crystalline product which separated was collected by filtration and dried to give 33 g (66percent yield) of 3,4-bis(p-toluyloxy)phenyl N-(tert-butyl)aminomethyl ketone hydrochloride, indicated to be essentially pure by thin layer chromatography.
  • 17
  • [ 4138-26-5 ]
  • [ 874-60-2 ]
  • [ 1050446-96-2 ]
YieldReaction ConditionsOperation in experiment
76% Example 11Method for producing (R)-1-(p-methylbenzoyl)<strong>[4138-26-5]nipecotamide</strong> Concentrated sulfuric acid is added to the reaction mixture obtained in Example 4 (amount: 30 g, net weight of (R)-<strong>[4138-26-5]nipecotamide</strong>: 3 g) to adjust the pH to 9. To the mixture, p-Methylbenzoyl chloride (8.0 g, 2.2 equivalents) was slowly added dropwise, and the pH of the reaction mixture was kept from 7 to 9 by a 30percent aqueous sodium hydroxide solution. After completion of the dropwise addition, the solution was stirred at 15° C. for 3 hours and the precipitated crystal was filtered off. The crystal was dried under reduced pressure to obtain the title compound as white crystal (4.4 g, yield: 760).1H NMR (400 MHz, CDCl3): delta7.42-7.22 (m, 4H), 6.56 (brs, 2H), 5.60 (brd, 1H), 4.18-3.18 (m, 4H), 2.18-1.40 (m, 4H)
  • 18
  • [ 1765-93-1 ]
  • [ 874-60-2 ]
  • [ 530-46-1 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; In toluene; at 100℃; for 2h;Schlenk technique; General procedure: An oven-dried Schlenk flask, equipped with a magnetic stir bar, septum and a condenser was charged with acyl chloride (1.0 mmol), arylboronic acid (1.0 mmol), NaOH (4 mmol) and 5.0 mL of toluene. The flask was immersed and stirred in an oil bath at 100 °C. Upon complete consumption of starting materials as determined by GC analysis, the water (10.0 mL) was added. The reaction mixture was extracted with diethyl ether (3 × 5.0 mL). The combined organic layer was collected, dried over anhydrous Na2SO4 and concentrated in vacuum to afford product which was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9:1 or 8:2).
45% With C30H38Cl2N8Pd(2+)*2Cl(1-); sodium carbonate; In water; acetone; at 60℃; for 12h; General procedure: The catalyst (3.8 mg, 1.0 molpercent), Na2CO3 (170 mg, 1.6 mmol), H2O (1.5 mL) and acetone (1.5 mL) was added into a 25 mL schlenk flask, then the reactor was stirred at room temperature for several minutes to dissolve the catalyst and base homogenously. Subsequently, benzoyl chloride (1.0 mmol) and boronic acid (1.2 mmol) were introduced. Then the flask was immersed in an oil bath preheated at 60 °C for 12 h. After the reaction was completed, the mixture was extracted with diethyl ether, and the combined organic layer was dried over anhydrous Na2SO4 and was subsequently purified by flash chromatography using silica gel (petroleum ether/ethyl acetate = 20:1) yielding the desired products.
  • 19
  • [ 492-30-8 ]
  • [ 874-60-2 ]
  • [ 25137-77-3 ]
  • [ 53008-95-0 ]
  • 20
  • [ 492-30-8 ]
  • [ 874-60-2 ]
  • 2-C-methyl-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranose [ No CAS ]
  • 2-C-methyl-3,5-di-O-(4-methylbenzoyl)-α-D-ribofuranose [ No CAS ]
  • 21
  • [ 874-60-2 ]
  • [ 192130-34-0 ]
  • [ 1235230-54-2 ]
  • 22
  • [ 932738-80-2 ]
  • [ 874-60-2 ]
  • [ 1414953-52-8 ]
  • 23
  • [ 932738-80-2 ]
  • [ 874-60-2 ]
  • [ 1414953-54-0 ]
  • 24
  • [ 2040-90-6 ]
  • [ 874-60-2 ]
  • [ 1443037-91-9 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; In dichloromethane; at 0 - 20℃; for 3h; General procedure: 2-Chloro-6-fluoro phenol (1, 0.2054 mol) was dissolved in DCM, triethylamine (TEA, 0.4519 mol) was added and the reaction mixture was cooled to 0 °C. A solution of benzoyl chloride derivatives (2a-e, 0.2157 mol) in DCM was added slowly to the above mixture and stirred for 3 h. Then the reaction mass was diluted with DCM (200 mL), washed with 10percent sodium hydroxide solution (3 x 30 mL), water (3 x 30 mL), brine (2 x 60 mL), and again with water (3 x 30 mL). The organic layer was dried over sodium sulfate and the solvent was evaporated to achieve compounds 3a-e.
96% With triethylamine; In dichloromethane; at 0 - 20℃; for 3h; General procedure: 2-Chloro-6-fluoro phenol (1, 0.20 mol) was dissolved indichloro methane (DCM) and triethylamine (TEA, 0.45 mol) wasadded to it. Then the reaction mixture was cooled to 0 C. Further,a solution of substituted benzoyl chloride 2a?d (0.21 mol) in DCMwas slowly added to the reaction mixture and stirred for 3 h andthe completion of the reaction was monitored by TLC using 4:1n-hexane: ethyl acetate solvent mixture. Then the reaction masswas diluted with DCM (100 ml), washed with 10percent sodium hydroxidesolution (3 40 ml), followed by water (3 30 ml). Theorganic layer was dried over sodium sulphate and the solidobtained after evaporation of the solvent was recrystallized fromethanol to give compounds 3a?d. [21] Compound (3a) is taken asa representative example to explain physical and characterizationdata.
  • 26
  • [ 1885-32-1 ]
  • [ 874-60-2 ]
  • [ 1470152-65-8 ]
YieldReaction ConditionsOperation in experiment
71% With pyridine; In tetrahydrofuran; at 20℃; for 16h; 3- Methyl-2-(4-methylbenzamido)benzamide (53b). Dry pyridine (205 mg, 2.6 mmol) was added to <strong>[1885-32-1]2-amino-3-methylbenzamide</strong> 5297 (300 mg, 2.0 mmol) in dry tetrahydrofuran (5.0 mL), followed by 4-nitrobenzoyl chloride (340 mg, 2.2 mmol) in dry tetrahydrofuran (5.0 mL). The mixture was stirred for 16 h. Evaporation and chromatography (ethyl acetate / petroleum ether 1 :1? 4:1) gave 3-methyl-2-(4- methylbenzamido)benzamide 53b (380 mg, 71%) as a white solid: mp 237-239C; 1H NMR ((CD3)2SO) delta 2.27 (3 H, s, 3-Me), 2.44 (3 H, s, Ph 4-Me), 7.31 (1 H, t, J = 7.6 Hz, 5-H), 7.39 (2 H, d, J = 7.9 Hz, Ph 3,5-H2), 7.44-7.50 (3 H, m, 4,6-H2 + NHH), 7.75 (1 H, s, NHH), 7.91 (2 H, d, J = 7.9 Hz, Ph 2,6-H2), 10.22 (1 H, s, NH); 13C NMR ((CD3)2SO) (HSQC / HMBC) delta 18.38 (3-Me), 20.98 (Ph 4-Me), 125.80 (5-C), 125.87 (6-C), 127.51 (Ph 2,6-C2), 129.01 (Ph 3,5-C2), 131.48 (Ph 1-C), 32.17 (4-C), 132.68 (1 -C), 134.65 (2-C), 135.94 (3-C), 141.63 (Ph 4-C), 164.92 (NHCO), 169.77 (CONH2); MS (electron impact) m/z 269.1261 (M)+ (C16H17N202 requires 269.1290).
  • 27
  • [ 22259-53-6 ]
  • [ 874-60-2 ]
  • [ 1328765-51-0 ]
  • 28
  • [ 17151-47-2 ]
  • [ 874-60-2 ]
  • [ 530-46-1 ]
YieldReaction ConditionsOperation in experiment
89% With palladium diacetate; In chloroform; at 60℃; for 2h;Inert atmosphere; General procedure: After the reaction of arylboronic acid (1 mmol) with tributyltin methoxide (0.321 g, 1 mmol) at 100 C for 1 h under solvent-free conditions, chloroform (4 mL) was added to the reaction mixture at room temperature. Either Pd(OAc)2 (0.0022 g, 0.01 mmol) or PdCl2 (0.0017 g, 0.01 mmol) and tri(2-furyl)phosphine (0.0046 g,0.02 mmol) were added under an argon gas stream, followed by addition of aroyl chloride (1 mmol) at room temperature. The resulting mixture was heated in a heating block with stirring at 60 C for 2 h. The reaction mixture was filtered through a Celite pad, and the solvent was removed under reduced pressure. After addition of THF (5 mL) and 3 M NaOH (1 mL) to the residue, the mixture was stirred for 0.5 h at room temperature and then diluted with H2O (4 mL). The aqueous phase was extracted with EtOAc (35 mL) and organic layers were washed with brine (5 mL) dried over Na2SO4, filtered, and then concentrated in vacuo. The residue was purified by column chromatography on silica gel to give pure diaryl ketone.
  • 29
  • [ 30465-68-0 ]
  • [ 874-60-2 ]
  • 8-chloro-10-(5-methoxyquinolin-8-yl)-3-methyldibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]
  • 30
  • [ 30465-68-0 ]
  • [ 874-60-2 ]
  • N-(4-methylbenzoyl)(5-methoxy)-8-quinolinamine [ No CAS ]
  • 31
  • [ 52522-40-4 ]
  • [ 24431-15-0 ]
  • [ 874-60-2 ]
  • [Pd(p-tolyl)HCNBnCO(p-tolyl)]2 [ No CAS ]
  • 33
  • [ 492-30-8 ]
  • [ 874-60-2 ]
  • [ 25137-77-3 ]
YieldReaction ConditionsOperation in experiment
61% With triethylamine; In ethyl acetate; for 2h;Cooling with ice; The 2-C-methyl-D- ribotide -1,4-lactone (1.62g, 10mmoL) suspended in 40 ml of ethyl acetate, under the condition of ice bath, by adding 4-methyl benzoyl chloride (2.08g, 20mmoL, 2eq), slowly add triethylamine (3.0 ml, 22mmoL, 2.2eq), 2 hours to drop end, reaction sleepovers. Filtering, with 20 ml ethyl acetate wash the filter cake, combined with the phase, with saturated sodium bicarbonate, 1M dilute hydrochloric acid and saturated salt water washing, drying by anhydrous magnesium sulphate. Concentrated after filtering, column separation to obtain 2.43g white solid, yield 61percent.
With triethylamine; In ethyl acetate;Cooling with ice; General procedure: General procedure (A) for the acylation: 2-C-methyl-D-ribono-gamma-lactone 1 (1.62 g, 10.0 mmol) was suspended in ethyl acetate (20 mL), followed by the addition of acyl chloride (2.6 g, 20 mmol, 2 eq) under ice bath. To this solution was slowly added triethylamine (3.0 mL, 22 mmol, 2.2 eq), and the reaction mixture was stirred overnight. The insoluble substance was filtrated away, and washed with ethyl acetate (20 mL). The combined filtrate was washed with saturated NaHCO3 solution (20 mL), 1 M HCl (20 mL x 2) and brine (20 mL), respectively, then dried over Na2SO4 and concentrated. The obtained residue was purified by silca column chromatography or slurryed with toluene/petroleum ether to afford 2.
  • 34
  • [ 874-60-2 ]
  • [ 33332-28-4 ]
  • N-(6-chloropyrazin-2-yl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% General procedure: A mixture of dry dichloromethane (DCM, 2 mL) and dry pyridine (475 mg, 6 mmol, 3 molarequiv) was put into 25 mL round-bottom flask, closed with a stopper and cooled in a freezer forapproximately 15 min. A selected benzoyl chloride (2.4 mmol, 1.2 equiv) was diluted with dry DCM(5 mL) and added dropwise to the cooled (ice bath) pyridine/DCM mixture under stirring, and the mixture was stirred for additional 5 min in the closed flask. 2-Aminopyrazine (190 mg, 2 mmol,1 equiv) or 6-chloropyrazin-2-amine (259 mg, 2 mmol, 1 equiv) was dissolved in DCM (2 mL) andadded dropwise to the cooled reaction mixture over 10 min upon stirring. After additional 15 min,the reaction was removed from the ice bath and stirred at laboratory temperature. The progress ofreaction was monitored by TLC (silica plates, 33percent EtOAc in hexane). After 2 h, no significant furtherincrease in the spot of the product was observed, so the reaction was ended and worked-up.The reaction mixture was adsorbed on silica (4 g) by evaporating the solvents underreduced pressure. The mixture on silica was used for solid loading the flash chromatographypre-column. The separation used the following conditions: manually filled silica column (30 g),continuous gradient elution 0?50percent EtOAc in hexane, flow rate 35 mL/min, detection wavelength280 nm, monitoring wavelength 260 nm. Fractions containing pure product were combined andsolvents were evaporated under reduced pressure to yield solid product. If needed, the productswere recrystallized from hot EtOH, the crystallization was induced by cooling and addition of water.The products were isolated as white solids. In several cases, the final products were still contaminatedwith non-specified impurity of brown color. This impurity was easily removed by dispersing theproduct in small amount of hexane and immersion of a vertical piece of filtration paper into thisdispersion. The impurity was soluble in hexane and rose by capillary action to the filtration paper.
  • 35
  • [ 52522-40-4 ]
  • [ 874-60-2 ]
  • [ 161265-03-8 ]
  • (Xantphos)Pd(CO(C6H4CH3))(Cl) [ No CAS ]
 

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