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[ CAS No. 157665-52-6 ] {[proInfo.proName]}

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Product Details of [ 157665-52-6 ]

CAS No. :157665-52-6 MDL No. :MFCD08703397
Formula : C11H12FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CXQXHHIIMBWMCH-UHFFFAOYSA-N
M.W : 241.22 Pubchem ID :10444351
Synonyms :

Safety of [ 157665-52-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 157665-52-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 157665-52-6 ]

[ 157665-52-6 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 157665-52-6 ]
  • [ 157665-53-7 ]
YieldReaction ConditionsOperation in experiment
98% With ammonium formate In ethanol
82% With hydroxylamine hydrochloride; iron In ethanol; water at 95℃; for 1.5h; 1.11A General Method 9A: Nitro Reduction with Iron/AmmoniumChloride General procedure: [0566] 10 eq. of ammonium chloride were dissolved in anethanol/water mixture (2: 1) (about 2M), the mixture washeated to 95° C. and the nitroaryl compound (1 eq.) wasadded. 3 eq. of iron powder were added in small portions overa period ofl h. The reaction mixture was then stirred at 95° C.for 30 min, and the hot mixture was then filtered throughkieselguhr. The filter cake was washed with ethanol and thefiltrate was freed from ethanol under reduced pressure. Theaqueous phase that remained was extracted three times withdiethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodiumsulphate), filtered and concentrated under reduced pressure.The crude product was then purified either by normal phasechromatography (mobile phase: cyclohexane/ethyl acetatemixtures or dichloromethane/methanol mixtures) or by preparativeRP-HPLC (water/acetonitrile gradient or water/methanol gradient).
  • 2
  • [ 157665-51-5 ]
  • [ 75-65-0 ]
  • [ 157665-52-6 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium 1.) hexane, 20 deg C, 20 min, 2.) hexane, THF, 22 h; Yield given. Multistep reaction;
  • 3
  • [ 288-32-4 ]
  • [ 157665-52-6 ]
  • [ 233671-61-9 ]
YieldReaction ConditionsOperation in experiment
82% In dimethyl sulfoxide at 100℃; for 1h;
  • 4
  • [ 1072-62-4 ]
  • [ 157665-52-6 ]
  • [ 233671-62-0 ]
YieldReaction ConditionsOperation in experiment
75% In dimethyl sulfoxide at 100℃;
  • 5
  • [ 527-73-1 ]
  • [ 157665-52-6 ]
  • [ 197089-32-0 ]
YieldReaction ConditionsOperation in experiment
57% With sodium hydride In dimethyl sulfoxide at 100℃; for 18h;
  • 6
  • [ 42383-61-9 ]
  • [ 157665-52-6 ]
  • [ 197089-38-6 ]
YieldReaction ConditionsOperation in experiment
61% With triethylamine In dimethyl sulfoxide at 100℃; for 3h;
  • 7
  • [ 403-21-4 ]
  • [ 75-65-0 ]
  • [ 157665-52-6 ]
YieldReaction ConditionsOperation in experiment
93% With 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate In chloroform at 100℃; for 2h; A2 Synthesis of Compound 2E. In a 500 mL flame dried round bottom flask, 3-fluoro-4-nitro-benzoic acid (5 g, 27.01 mmol) was diluted in chloroform (130.32 mL) (ca.) to provide a suspension. 1-Methylimidazole (4.88 g, 59.42 mmol, 4.74 mL) and TCFH (8.34 g, 29.71 mmol) were then added to the suspension. /-BuOH was subsequently added (20.02 g, 270.11 mmol), and the flask was then transferred to an oil bath and stirred for 2 hours at 100 °C. The reaction mixture is concentrated onto silica and purified by flash column chromatography to provide Compound 2E (6.07 g, 25.16 mmol, 93% yield).
79% With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h;
77% Stage #1: 3-fluoro-4-nitrobenzoic acid With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: <i>tert</i>-butyl alcohol With dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; 42 A solution of 3-Fluoro-4-Nitro benzoic acid (2.0Og, 10.8 mmol) in 50% DMF/CH2C12 (60 ml) was put on ice for 15 minutes. To the solution EDC (2.1g, 11 mmol) was added.The solution was stirred in the cold for another 15 minutes, t-butanol (3.7g , 50 mmol) was then added, followed by DMAP (lOOmg). The solution was stirred at room temperature overnight.Upon completion (TLC), the reaction mixture was diluted with ethyl acetate (300ml) , washed with water then with IN NaOH solution and finally with brine. The organic phase was evaporated to dryness. The residue was washed down a column eluded with 3% methanol inCH2Cl2. the pooled fractions were evaporated to dryness to give 2g (77%) of the desired product.
75% Stage #1: 3-fluoro-4-nitrobenzoic acid; <i>tert</i>-butyl alcohol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Cooling with ice; Stage #2: With sodium hydrogencarbonate In dichloromethane; water 23.1 To a solution of 3-fluoro-4-nitrobenzoic acid (2.00 g) in methylene chloride (32 mL) were added under ice-cooling tert-butanol (4.2 mL), 4-dimethylaminopyridine (198 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.47 g), and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with chloroform. The organic layer was distilled under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate = 99/1 to 92/8) to give tert-butyl 3-fluoro-4-nitrobenzoate (1.94 g) as a pale yellow powder (yield 75%).
34% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

  • 8
  • [ 7569-26-8 ]
  • [ 157665-52-6 ]
  • tert-butyl 3-fluoro-5-[(4-methylphenyl)sulfonyl]methyl}-4-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 0.0833333h;
  • 9
  • [ 13557-25-0 ]
  • [ 157665-52-6 ]
  • tert-butyl 3-tert-butoxy-4-nitrobenzoate [ No CAS ]
  • tert-butyl 3-fluoro-4-nitro-5-[1-(phenylsulfonyl)ethyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 46% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50℃; for 0.0833333h;
  • 10
  • [ 446-34-4 ]
  • [ 157665-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / Na2Cr2O7*2H2O, H2SO4 / H2O / 1 h / 90 °C 2: 79 percent / DMAP, DCC / CH2Cl2 / 24 h
  • 11
  • [ 157665-52-6 ]
  • [ 233671-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / dimethylsulfoxide / 1 h / 100 °C 2: 77 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr
  • 12
  • [ 157665-52-6 ]
  • [ 233671-70-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / dimethylsulfoxide / 1 h / 100 °C 2: 77 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: 58 percent / acetic acid / Ambient temperature
  • 13
  • [ 157665-52-6 ]
  • [ 233671-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / dimethylsulfoxide / 100 °C 2: 24 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr
  • 14
  • [ 157665-52-6 ]
  • [ 197089-34-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 57 percent / NaH / dimethylsulfoxide / 18 h / 100 °C 2: 97 percent / H2 / 10 percent Pd/C / acetic acid / 24 h / 760 Torr
Multi-step reaction with 2 steps 1: 61 percent / NEt3 / dimethylsulfoxide / 3 h / 100 °C 2: H2 / 10 percent Pd/C / acetic acid / 760 Torr
  • 15
  • [ 157665-52-6 ]
  • [ 233671-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / dimethylsulfoxide / 100 °C 2: 24 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: 84 percent / acetic acid / Ambient temperature
  • 16
  • [ 157665-52-6 ]
  • [ 197089-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 57 percent / NaH / dimethylsulfoxide / 18 h / 100 °C 2: 97 percent / H2 / 10 percent Pd/C / acetic acid / 24 h / 760 Torr 3: acetic acid / 96 h / Ambient temperature
Multi-step reaction with 3 steps 1: 61 percent / NEt3 / dimethylsulfoxide / 3 h / 100 °C 2: H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: acetic acid / 96 h / Ambient temperature
  • 17
  • [ 157665-52-6 ]
  • 4-acetylamino-3-(imidazol-1'-yl)-benzoic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 82 percent / dimethylsulfoxide / 1 h / 100 °C 2: 77 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: 58 percent / acetic acid / Ambient temperature 4: 80 percent / CH2Cl2 / Ambient temperature
  • 18
  • [ 157665-52-6 ]
  • 4-amino-3-(2'-aminoimidazol-1'-yl)-benzoic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 57 percent / NaH / dimethylsulfoxide / 18 h / 100 °C 2: 97 percent / H2 / 10 percent Pd/C / acetic acid / 24 h / 760 Torr 3: 91 percent / CH2Cl2 / 2 h / Ambient temperature
Multi-step reaction with 3 steps 1: 61 percent / NEt3 / dimethylsulfoxide / 3 h / 100 °C 2: H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: 91 percent / CH2Cl2 / 2 h / Ambient temperature
  • 19
  • [ 157665-52-6 ]
  • 4-acetylamino-3-(2'-amino-imidazol-1'-yl)-benzoic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 57 percent / NaH / dimethylsulfoxide / 18 h / 100 °C 2: 97 percent / H2 / 10 percent Pd/C / acetic acid / 24 h / 760 Torr 3: acetic acid / 96 h / Ambient temperature 4: 92 percent / CH2Cl2 / 2 h / Ambient temperature
Multi-step reaction with 4 steps 1: 61 percent / NEt3 / dimethylsulfoxide / 3 h / 100 °C 2: H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: acetic acid / 96 h / Ambient temperature 4: 92 percent / CH2Cl2 / 2 h / Ambient temperature
  • 20
  • [ 157665-52-6 ]
  • 4-acetylamino-3-(2'-ethylimidazol-1'-yl)-benzoic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 75 percent / dimethylsulfoxide / 100 °C 2: 24 percent / H2 / 10 percent Pd/C / acetic acid / 760 Torr 3: 84 percent / acetic acid / Ambient temperature 4: 41 percent / CH2Cl2 / Ambient temperature
  • 21
  • [ 403-21-4 ]
  • [ 157665-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 62 percent / SOCl2 / toluene / 3 h / Heating 2: 1.) BuLi / 1.) hexane, 20 deg C, 20 min, 2.) hexane, THF, 22 h
  • 22
  • [ 157665-52-6 ]
  • [ 157665-54-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature
  • 23
  • [ 157665-52-6 ]
  • [ 157665-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 50 percent / SOCl2 / CH2Cl2 / 0.75 h / Heating
  • 24
  • [ 157665-52-6 ]
  • 4-[Bis-(2-chloro-ethyl)-amino]-3-fluoro-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 50 percent / SOCl2 / CH2Cl2 / 0.75 h / Heating 4: 36 percent / THF / 0.67 h / Ambient temperature
  • 25
  • [ 157665-52-6 ]
  • [ 157665-56-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 23 percent / pyridine / 1.) 2-4 deg C, 40 min, 2.) 50 deg C, 30 min
  • 26
  • [ 157665-52-6 ]
  • 4-[(2-Chloro-ethyl)-(2-methanesulfonyloxy-ethyl)-amino]-3-fluoro-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 23 percent / pyridine / 1.) 2-4 deg C, 40 min, 2.) 50 deg C, 30 min 4: 95 percent / TFA / 0.67 h / Ambient temperature
  • 27
  • [ 157665-52-6 ]
  • [ 157665-55-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 32 percent / pyridine / 1.) 2-4 deg C, 40 min, 2.) 50 deg C, 30 min
  • 28
  • [ 157665-52-6 ]
  • 3-fluoro-4-<bis<2-(mesyloxy)ethyl>amino>benzoic acid trifluoroacetate salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / ammonium formate / 10percent Pd/C / ethanol 2: 71 percent / HOAc / 48 h / Ambient temperature 3: 32 percent / pyridine / 1.) 2-4 deg C, 40 min, 2.) 50 deg C, 30 min 4: 100 percent / 0.67 h / Ambient temperature
  • 29
  • NaSO2Me [ No CAS ]
  • [ 157665-52-6 ]
  • 3,4-bis-methanesulfonyl-benzoic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; hexane; water; dimethyl sulfoxide; ethyl acetate 27.H 3,4-bis-Methanesulfonyl-benzoic acid Method H 3,4-bis-Methanesulfonyl-benzoic acid To 3-fluoro-4-nitro-benzoic acid tert-butyl ester (0.5 g) in DMSO was added NaSO2Me. The reaction mixture was heated to 100° C. for 24 hours. A mixture of water, diethyl ether and ethyl acetate (1:1:1) was added and the resulting mixture was extracted with diethyl ether/ethyl acetate (1:1). The organic extracts were combined, dried with MgSO4 and concentrated to leave a residue which was purified by chromatography (using 80% ethyl acetate/20% hexane) to give 3,4-bis-methanesulfonyl-benzoic acid tert-butyl ester (366 mg). 1H NMR (399.98 MHz, DMSO-D6) 1.59 (9H, s), 3.50 (3H, s) 3.52 (3H, s), 8.37-8.65 (3H, m).
  • 30
  • [ 4244-84-2 ]
  • [ 157665-52-6 ]
  • [ 1090903-00-6 ]
YieldReaction ConditionsOperation in experiment
86% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; 3-fluoro-4-nitro-benzoic acid tert-butyl ester (Ig, 4.14mmol) and Beta-Alanine ethyl ester hydrochloride 1.037g, 6.75 mmol) were dissolved in DMF (10ml). To the solution DIEA 0.872 g, 6.75 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml), extracted with Ethyl acetate <n="191"/>3 x, dried over MgSCH, filtered and evaporated to dryness to afford 1.2g of solid was obtained (86percent).
  • 31
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-(cyclohexyloxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h 1.2: 1 h / 20 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C / 760.05 Torr
  • 32
  • [ 157665-52-6 ]
  • tert-butyl 4-[6-(cyclohexylmethyl)pyridine-2-amido]-3-(cyclohexyloxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h 1.2: 1 h / 20 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C / 760.05 Torr 3.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C 3.2: 20 °C
  • 33
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-(phenylsulfanyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 °C 2: ammonium chloride; iron / water; ethanol / 0.75 h / Reflux
  • 34
  • [ 157665-52-6 ]
  • tert-butyl 4-[6-(cyclohexylmethyl)pyridine-2-amido]-3-(phenylsulfanyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 °C 2.1: ammonium chloride; iron / water; ethanol / 0.75 h / Reflux 3.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C 3.2: 20 °C
  • 35
  • [ 157665-52-6 ]
  • 4-[6-(cyclohexylmethyl)pyridine-2-amido]-3-(cyclohexyloxy)benzoic acid hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h 1.2: 1 h / 20 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C / 760.05 Torr 3.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C 3.2: 20 °C 4.1: hydrogenchloride; triethylsilane / water; 1,4-dioxane / 60 h / 20 °C
  • 36
  • [ 157665-52-6 ]
  • 4-[6-(cyclohexylmethyl)pyridine-2-amido]-3-(phenylsulfanyl)benzoic acid hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 °C 2.1: ammonium chloride; iron / water; ethanol / 0.75 h / Reflux 3.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C 3.2: 20 °C 4.1: hydrogenchloride; triethylsilane / water; 1,4-dioxane / 72 h / 20 °C
  • 37
  • [ 157665-52-6 ]
  • [ 108-93-0 ]
  • tert-butyl 3-(cyclohexyloxy)-4-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: cyclohexanol With sodium hydride In tetrahydrofuran for 0.0833333h; Stage #2: 3-fluoro-4-nitrobenzoic acid t-butyl ester In tetrahydrofuran at 20℃; for 1h;
  • 38
  • [ 108-98-5 ]
  • [ 157665-52-6 ]
  • tert-butyl 4-nitro-3-(phenylsulfanyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64 mg With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 3h;
  • 39
  • [ 39982-01-9 ]
  • [ 403-21-4 ]
  • [ 157665-52-6 ]
YieldReaction ConditionsOperation in experiment
With dmap In tetrahydrofuran at 20 - 40℃; for 3h; tert-Butyl 3-fluoro-4-nitrobenzoate 3-Fluoro-4-nitrobenzoic acid (2.60 g, 14.0 mmol) was dissolved in THF (30 mL), the mixture treated with Boc anhydride (6.13 g, 28.1 mmol) and DMAP (525 mg, 4.21 mmol), and then stirred at RT. A thick slurry quickly formed and was then stirred for 3 h at 40° C. during which time the slurry became a tan solution. After concentrating the reaction mixture under reduced pressure, the residue was dissolved in EtOAc, adsorbed onto silica gel and then eluted through a short pad of silica gel with 50% EtOAc/Heptane. The filtrate was concentrated under reduced pressure to yield Intermediate 29 (8.88 g, 68%) as a yellow solid. 1H NMR (600 MHz, CDCl3) δ 8.05-8.09 (m, 1H), 7.86-7.90 (m, 2H), 1.61 (s, 9H).
  • 40
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-((oxazol-2-ylmethyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 2585.81 Torr
  • 41
  • [ 157665-52-6 ]
  • tert-butyl 2-(chloromethyl)-1-(oxazol-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 2585.81 Torr 3: toluene-4-sulfonic acid / acetonitrile / 3 h / 60 °C
  • 42
  • [ 157665-52-6 ]
  • tert-butyl 2-((4-(6-((4-cyano-2-fluorobenzyl)oxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxazol-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 2585.81 Torr 3: toluene-4-sulfonic acid / acetonitrile / 3 h / 60 °C 4: potassium carbonate / acetonitrile / 2 h / 60 °C
  • 43
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-(((1-ethyl-1H-imidazol-5-yl)methyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 60 °C 2: water; ammonium chloride / methanol / 0.83 h / 80 °C
  • 44
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-(2-(4-(6-((4-chloro-2-fluorobenzyl)oxy)pyridin-2-yl)piperidin-1-yl)-N-((1-ethyl-1H-imidazol-5-yl)methyl)acetamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: water; ammonium chloride / methanol / 0.83 h / 80 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide 3.2: 16 h / 30 °C
  • 45
  • [ 157665-52-6 ]
  • tert-butyl 2-((4-(6-((4-chloro-2-fluorobenzyl)oxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-((1-ethyl-1H-imidazol-5-yl)methyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: water; ammonium chloride / methanol / 0.83 h / 80 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide 3.2: 16 h / 30 °C 4.1: acetic acid / 16 h / 60 °C
  • 46
  • [ 157665-52-6 ]
  • 2-[(4-{6-[(4-chloro-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(1-ethyl-1H-imidazol-5-yl)methyl]-1H-benzimidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: water; ammonium chloride / methanol / 0.83 h / 80 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide 3.2: 16 h / 30 °C 4.1: acetic acid / 16 h / 60 °C 5.1: trifluoroacetic acid / dichloromethane / 16 h / 10 °C
  • 47
  • [ 157665-52-6 ]
  • 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-(1,3-oxazol-2-ylmethyl)-1H-benzimidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 2585.81 Torr 3: toluene-4-sulfonic acid / acetonitrile / 3 h / 60 °C 4: potassium carbonate / acetonitrile / 2 h / 60 °C 5: trifluoroacetic acid / 1,2-dichloro-ethane / 4 h / 70 °C
  • 48
  • (1-ethyl-1H-imidazol-5-yl)methanamine [ No CAS ]
  • [ 157665-52-6 ]
  • tert-butyl 3-(((1-ethyl-1H-imidazol-5-yl)methyl)amino)-4-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 60℃; for 16h; 10A-02.1 Step 1 To a solution of Intermediate 29 (200 mg, 0.829 mmol) in DMF (8 mL) was added (1-ethyl-1H-imidazol-5-yl)methanamine (104 mg, 0.829 mmol) and NaHCO3 (348 mg, 4.15 mmol). The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was poured into water (10 mL) and then extracted with EtOAc (2*30 mL). The combined organic extracts were washed with brine (2*20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (0 to 5% MeOH/DCM) to give tert-butyl 3-(((1-ethyl-1H-imidazol-5-yl)methyl)amino)-4-nitrobenzoate (105 mg, 37%) as a pale red oil. 1H NMR (CDCl3) δ 8.23 (d, 1H), 7.96 (br s, 1H), 7.66 (d, 1H), 7.57 (s, 1H), 7.28 (dd, 1H), 7.12 (s, 1H), 4.54 (d, 2H), 4.00 (q, 2H), 1.62 (s, 9H), 1.47 (t, 3H).
With triethylamine In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;
  • 49
  • [ 1041053-44-4 ]
  • [ 157665-52-6 ]
  • te rt-Butyl 4-nitro-3-[(1,3-oxazol-2-ylmethyl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2.0h; To a suspension of the oxazol-2-ylmethanamine HC1 salt (491 mg, 3.65 mmol) and Intermediate 29 (800 mg, 3.32 mmol) in DMF (5 mE) was added K2C03 (1.04 g, 6.63 mmol). The reaction was stirred at 60 C. for 2 h. Additional oxazol-2-ylmethanamine HC1 salt (100 mg, 1.0 mmol) was added and reaction stirred for an additional 30 mm at 60 C. The reaction was cooled to RT then diluted with water (30 mE) and extracted with EtOAc (60 mE). The organic layer was washed with water, then brine, dried over Na2504, filtered and concentrated under reduced pressure. The orange residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc/heptane gradient) to deliver teflbutyl 4-nitro-3-((oxazol-2-ylmethyl)amino)benzoate (764 mg, 75%) as an orange solid. ?H NMR (CDC13) oe 8.48 (br s, 1H), 8.23 (d, 1H), 7.68 (d, 1H), 7.61 (d, 1H), 7.28 (dd, 1H), 7.15 (s, 1H), 4.72 (d, 2H), 1.60 (s, 9H).
75% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2.5h; To a suspension of 1 -(1 ,3-oxazol-2-yl)methanamine, hydrochloride salt (491 mg, 3.65 mmol) and fe/f-butyl 3-fluoro-4-nitrobenzoate (800 mg, 3.32 mmol) in A/,A/-dimethylformamide (5 mL) was added potassium carbonate (1 .04 g, 6.63 mmol). The reaction was stirred at 60 C for 2 hours. Additional 1 -(1 ,3-oxazol-2-yl)methanamine, hydrochloride salt (100 mg, 1 .0 mmol) was added and the reaction was stirred for an additional 30 minutes at 60 C. The reaction was cooled to room temperature then diluted with water (30 mL) and extracted with EtOAc (60 mL). The organic layer was washed with water, then saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The orange residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc / heptane gradient) to deliver P25 (764 mg, 75%) as an orange solid. NMR (CDCI3) d 8.48 (br s, 1 H), 8.23 (d, 1 H), 7.68 (d, 1 H), 7.61 (d, 1 H), 7.28 (dd, 1 H), 7.15 (s, 1 H), 4.72 (d, 2H), 1 .60 (s, 9H).
  • 50
  • [ 157665-52-6 ]
  • [ 1090903-01-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr
  • 51
  • [ 157665-52-6 ]
  • [ 1090903-02-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr 3: tetrahydrofuran / 0.5 h / 90 °C
  • 52
  • [ 157665-52-6 ]
  • [ 1090903-04-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr 3.1: tetrahydrofuran / 0.5 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.58 h / 0 °C 4.2: 20 °C 5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
  • 53
  • [ 157665-52-6 ]
  • [ 1090903-03-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr 3.1: tetrahydrofuran / 0.5 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.58 h / 0 °C 4.2: 20 °C
  • 54
  • [ 157665-52-6 ]
  • 3-(3-naphtalen-2-ylmethyl-2-oxo-6-[(tetrahydro-furan-2-ylmethyl)carbamoyl]-2,3-dihydro-benzoimidazol-1-yl)propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr 3.1: tetrahydrofuran / 0.5 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.58 h / 0 °C 4.2: 20 °C 5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 6.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.5 h / 0 °C 6.2: 4 h / 20 °C 7.1: sodium hydroxide; water / methanol / 2 h / 20 °C
  • 55
  • [ 157665-52-6 ]
  • [ 1090903-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: hydrogen / palladium on activated carbon / ethanol / 760.05 Torr 3.1: tetrahydrofuran / 0.5 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.58 h / 0 °C 4.2: 20 °C 5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 6.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.5 h / 0 °C 6.2: 4 h / 20 °C
  • 56
  • [ 157665-52-6 ]
  • benzyl 4-(4-(2-aminocyclopropyl)phenylcarbamoyl)-2-(4-methylpiperazin-1-yl)phenylcarbamate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C / Sealed tube 2.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C / 2585.81 Torr 3.1: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 20 °C 5.1: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere 5.2: 2 h / Inert atmosphere 6.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 5 h / 20 °C
  • 57
  • [ 157665-52-6 ]
  • benzyl (4-((4-(2-((tert-butoxycarbonyl)amino)cyclopropyl)phenyl)carbamoyl)-2-(4-methylpiperazin-1-yl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C / Sealed tube 2.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C / 2585.81 Torr 3.1: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 20 °C 5.1: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere 5.2: 2 h / Inert atmosphere
  • 58
  • [ 157665-52-6 ]
  • tert-butyl 4-amino-3-(4-methylpiperazin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C / Sealed tube 2: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C / 2585.81 Torr
  • 59
  • [ 157665-52-6 ]
  • tert-butyl 4-(benzyloxycarbonylamino)-3-(4-methylpiperazin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C / Sealed tube 2: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C / 2585.81 Torr 3: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C
  • 60
  • [ 157665-52-6 ]
  • 4-(benzyloxycarbonylamino)-3-(4-methylpiperazin-1-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C / Sealed tube 2: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C / 2585.81 Torr 3: triethylamine / tetrahydrofuran / 1.5 h / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 20 °C
  • 62
  • [ 768-94-5 ]
  • [ 157665-52-6 ]
  • C21H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dimethyl sulfoxide at 60℃;
  • 63
  • [ 62-53-3 ]
  • [ 157665-52-6 ]
  • C17H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide 2: 10 wt% Pd(OH)2 on carbon; hydrogen
  • 64
  • [ 157665-52-6 ]
  • C27H40N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 60 °C 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 20 °C 3: sodium tris(acetoxy)borohydride / dichloromethane / 20 °C
  • 65
  • [ 157665-52-6 ]
  • C21H30N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 60 °C 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 20 °C
  • 66
  • [ 107269-68-1 ]
  • [ 157665-52-6 ]
  • Tert-butyl 3-(((2-methyl-2H-tetrazol-5-yl)methyl)amino)-4-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 55℃; for 10h; 226 Tert-butyl 3-(((2-methyl-2H-tetrazol-5-yl)methyl)amino)-4-nitrobenzoate: To a solution of tert-butyl 3-fluoro-4-nitrobenzoate (160 mg, 0.663 mmol) in THF (10 mL) was added diisoproylethylamine (0.35 mL, 2.00 mmol) and (2-methyl-2H-tetrazol-5-yl)methanamine hydrochloride (98 mg, 0.663 mmol). The resulting solution was heated to 55 °C for 10 hours. Upon completion the solvent was removed, the resulting residue taken up in EtOAc (150 mL), washed with brine (30 mL), concentrated and carried forward without further purification. ES/MS: 358.2 (M+Na+).
  • 67
  • [ 944154-51-2 ]
  • [ 157665-52-6 ]
  • Tert-butyl 4-nitro-3-((2,3-dimethoxy-3-oxopropyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane at 80℃; Tert-butyl 4-nitro-3-((2,3-dimethoxy-3-oxopropyl)amino)benzoate: 3-amino- 2-methoxy-propanoic acid hydrochloride (355 mg, 2.3 mmol) was suspended in DCM/methanol (5 mL, 3:1), and TMS diazomethane (2.0 M, 1.1 mL, 2.3 mmol) was added until a faint yellow color persisted. The reaction was quenched by addition of AcOH (~1 drop), concentrated to dryness, dissolved in MeTHF (3 mL), and again concentrated to dryness. To the resulting crude amino ester dissolved in MeTHF (3 mL), were added tert-butyl 3-fluoro-4-nitro-benzoate (500 mg, 2.1 mmol) and DIPEA (1.1 mL, 6.2 mmol). The mixture was stirred at 80 °C overnight. The reaction was then cooled, diluted with EtOAc, rinsed with aq NH4Cl, dried over Na2SO4, filtered, and concentrated: ES/MS: 355.1 (M+H+)
  • 68
  • [ 157665-52-6 ]
  • [ 109-85-3 ]
  • Tert-butyl 3-((2-methoxyethyl)amino)-4-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃; Tert-butyl 3-((2-methoxyethyl)amino)-4-nitrobenzoate: To a 500 mL RBF was added tert-butyl 3-fluoro-4-nitrobenzoate (10 g, 41.5 mmol). The material was dissolved in THF (150 mL), and 2-methoxyethanamine (7.2 mL, 82.9 mmol) and N,N-diisopropylethylamine (21.7 mL, 124 mmol) were added. The mixture was stirred at 50°C overnight. Afterward, the mixture was concentrated to remove most of the THF, and the crude material was dissolved in EtOAc (400 mL). The organics were washed with 50% NH4Cl (2x 100 mL) and with brine (1x 50 mL). The organics were subsequently dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was carried forward without further purification: ES/MS: 297.1 (M+H+); NMR (400 MHz, Chloroform-d) δ 8.21 (d, J = 8.9 Hz, 1H), 7.55 (d, J = 1.7 Hz, 1H), 7.20 (dd, J = 8.9, 1.7 Hz, 1H), 3.72 (dd, J = 5.8, 4.8 Hz, 2H), 3.57 (q, J = 5.2 Hz, 2H), 3.46 (s, 3H), 1.62 (s, 9H).
  • 69
  • [ 157665-52-6 ]
  • Tert-butyl 2-[[4-[6-[(4-cyano-2-fluoro-phenyl)methoxy]-2-pyridyl]-2-fluoro-phenyl]methyl]-3-(2,3-dimethoxy-3-oxo-propyl)benzimidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 80 °C 2.1: ammonium chloride; iron / ethanol; water / 0.75 h / 60 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 0.25 h / 50 °C 3.2: 1.58 h / 70 - 90 °C
  • 70
  • [ 157665-52-6 ]
  • Tert-butyl 4-amino-3-(((2-methyl-2H-tetrazol-5-yl)methyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 h / 55 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 16 h / 20 °C
  • 71
  • [ 157665-52-6 ]
  • Tert-butyl 2-(4-(6-((4-cyano-2-fluorobenzyl)oxy)pyridin-2-yl)-2-fluorobenzyl)-1-((2-methyl-2H-tetrazol-5-yl)methyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 h / 55 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 16 h / 20 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 3.2: 1.5 h / 80 °C
  • 72
  • [ 157665-52-6 ]
  • (x)C2HF3O2*C31H22F2N8O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 h / 55 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 16 h / 20 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 3.2: 1.5 h / 80 °C 4.1: N,N-dimethyl-formamide / 2 h / 40 °C
  • 73
  • [ 157665-52-6 ]
  • Tert-butyl 2-(4-bromo-2,5-difluorobenzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C
  • 74
  • [ 157665-52-6 ]
  • tert-butyl 2-[[4-[6-[(4-cyano-2-fluoro-phenyl)methoxy]-2-pyridyl]-2,5-difluoro-phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube
  • 75
  • [ 157665-52-6 ]
  • 2-(4-(6-((4-cyano-2-fluorobenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: dichloromethane / 4 h / 45 °C
  • 76
  • [ 157665-52-6 ]
  • Tert-butyl 2-((4-(2-((4-cyano-2-fluorobenzyl)oxy)thiazol-4-yl)-1H-pyrazol-1-yl)methyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h 3.2: 1 h / 60 °C
  • 77
  • [ 157665-52-6 ]
  • 2-((4-(2-((4-cyano-2-fluorobenzyl)oxy)thiazol-4-yl)-1H-pyrazol-1-yl)methyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h 3.2: 1 h / 60 °C 4.1: dichloromethane / 2 h / 50 °C / Sealed tube
  • 78
  • [ 157665-52-6 ]
  • tert-butyl 2-(4-(6-((4-cyanobenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: caesium carbonate / acetonitrile / 3 h / 20 °C
  • 79
  • [ 157665-52-6 ]
  • 2-(4-(6-((4-cyanobenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylic acid trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: caesium carbonate / acetonitrile / 3 h / 20 °C 7.1: dichloromethane / 2.5 h / 2.5 °C
  • 80
  • [ 157665-52-6 ]
  • tert-butyl 2-[[4-[6-[[2,3-difluoro-4-(trifluoromethyl)phenyl]methoxy]-2-pyridyl]-2,5-difluoro-phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / acetonitrile / 50 °C
  • 81
  • [ 157665-52-6 ]
  • 2-[[4-[6-[[2,3-difluoro-4-(trifluoromethyl)phenyl]methoxy]-2-pyridyl]-2,5-difluorophenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / acetonitrile / 50 °C 7.1: dichloromethane / 40 °C
  • 82
  • [ 157665-52-6 ]
  • 2-[[2,5-difluoro-4-[6-[(2-fluoro-4-pyrimidin-2-yl-phenyl)methoxy]-2-pyridyl]phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / toluene / 8 h / 70 °C 7.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 110 °C 8.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.17 h / 100 °C / Microwave irradiation 8.2: 1 h
  • 83
  • [ 157665-52-6 ]
  • 2-[[2,5-difluoro-4-[6-[[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]methoxy]-2-pyridyl]phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / toluene / 8 h / 70 °C 7.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.17 h / 100 °C / Microwave irradiation 7.2: 1 h
  • 84
  • [ 157665-52-6 ]
  • Tert-butyl 4-amino-3-((2-methoxyethyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication
  • 85
  • [ 157665-52-6 ]
  • tert-butyl 2-(2,5-difluoro-4-(6-hydroxypyridin-2-yl)benzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C
  • 86
  • [ 157665-52-6 ]
  • tert-butyl 2-(4-bromo-5-fluoro-2-(hydroxymethyl)benzyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3.2: 1 h / 100 °C
  • 87
  • [ 157665-52-6 ]
  • tert-butyl 2-[[4-[6-[(4-bromo-2-fluoro-phenyl)methoxy]-2-pyridyl]-2,5-difluoro-phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / toluene / 8 h / 70 °C
  • 88
  • [ 157665-52-6 ]
  • Tert-butyl 2-[[2,5-difluoro-4-[6-[[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]-2-pyridyl]phenyl]methyl]-3-(2-methoxyethyl)benzimidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 0.25 h / Sonication 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 3.2: 4 h / 70 °C 4.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(pinacol)diborane / 1,4-dioxane / 1.5 h / 100 °C 4.2: 1 h / 90 °C / Inert atmosphere; Sealed tube 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C 6.1: silver carbonate / toluene / 8 h / 70 °C 7.1: potassium propionate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 110 °C
  • 89
  • [ 157665-52-6 ]
  • Tert-butyl 4-amino-3-[(2,3-dimethoxy-3-oxo-propyl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 80 °C 2: ammonium chloride; iron / ethanol; water / 0.75 h / 60 °C
  • 90
  • [ 157665-52-6 ]
  • C14H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / diethyl ether / 3 h / 0 - 20 °C 2: zinc; ammonium chloride; water / acetone / 2 h / 25 °C
  • 91
  • [ 157665-52-6 ]
  • C27H33NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride / diethyl ether / 3 h / 0 - 20 °C 2: zinc; ammonium chloride; water / acetone / 2 h / 25 °C 3: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 3 h / 20 °C
  • 92
  • [ 157665-52-6 ]
  • C42H39ClF6N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / diethyl ether / 3 h / 0 - 20 °C 2.1: zinc; ammonium chloride; water / acetone / 2 h / 25 °C 3.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 3 h / 20 °C 4.1: chloroform / 0.17 h / 20 °C 4.2: 2 h / 110 °C / Sealed tube
  • 93
  • [ 157665-52-6 ]
  • 4‐(2‐(N‐(2‐chloro‐4‐fluorobenzyl)-(2,3,4,5,6‐pentafluorophenyl)sulfonamido)‐N‐(3,5‐dicyclopropylbenzyl)acetamido)‐3‐cyclopropoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / diethyl ether / 3 h / 0 - 20 °C 2.1: zinc; ammonium chloride; water / acetone / 2 h / 25 °C 3.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 3 h / 20 °C 4.1: chloroform / 0.17 h / 20 °C 4.2: 2 h / 110 °C / Sealed tube 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 94
  • [ 157665-52-6 ]
  • [ 123330-86-9 ]
YieldReaction ConditionsOperation in experiment
99% With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In N,N-dimethyl-formamide at 0℃; for 3h; A3 Synthesis of Compound 4 A. 2-(Methylsulfonyl-ethanol) (154 mg, 1.24 mmol) was added to a stirring solution of Compound 2E (200 mg, 829.14 pmol) in DMF (1.26 mL), and the resulting mixture was cooled to 0 °C. NaH (59 mg, 2.49 mmol) was then added, and the reaction was stirred for 3 hours. The reaction was then warmed to room temperature, quenched with a IN HC1 solution, and partitioned between ethyl acetate and brine. The organic layer was concentrated to dryness, and the residue was purified flash column chromatography to afford Compound 4A (198.5 mg, 827.6 pmol, 99% yield).
  • 95
  • [ 157665-52-6 ]
  • [ 137066-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride; 2-(methylsulfonyl)ethyl alcohol / N,N-dimethyl-formamide / 3 h / 0 °C 2: zinc; ammonium chloride; water / acetone / 1 h / 25 °C
  • 96
  • [ 157665-52-6 ]
  • C24H29NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride; 2-(methylsulfonyl)ethyl alcohol / N,N-dimethyl-formamide / 3 h / 0 °C 2: zinc; ammonium chloride; water / acetone / 1 h / 25 °C 3: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / 25 °C / Molecular sieve
  • 97
  • [ 157665-52-6 ]
  • C39H35ClF6N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydride; 2-(methylsulfonyl)ethyl alcohol / N,N-dimethyl-formamide / 3 h / 0 °C 2: zinc; ammonium chloride; water / acetone / 1 h / 25 °C 3: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / 25 °C / Molecular sieve 4: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / chloroform / 1 h / 110 °C / Sealed tube
  • 98
  • [ 157665-52-6 ]
  • C41H39ClF6N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium hydride; 2-(methylsulfonyl)ethyl alcohol / N,N-dimethyl-formamide / 3 h / 0 °C 2: zinc; ammonium chloride; water / acetone / 1 h / 25 °C 3: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / 25 °C / Molecular sieve 4: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / chloroform / 1 h / 110 °C / Sealed tube 5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 25 °C
  • 99
  • [ 157665-52-6 ]
  • 4‐(2‐(N‐(2‐chloro‐4‐fluorobenzyl)-(2,3,4,5,6‐pentafluorophenyl)sulfonamido)‐N‐(3,5‐dicyclopropylbenzyl)acetamido)‐3‐ethoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride; 2-(methylsulfonyl)ethyl alcohol / N,N-dimethyl-formamide / 3 h / 0 °C 2: zinc; ammonium chloride; water / acetone / 1 h / 25 °C 3: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / 25 °C / Molecular sieve 4: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / chloroform / 1 h / 110 °C / Sealed tube 5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 25 °C 6: trifluoroacetic acid / dichloromethane / 1 h / 25 °C
  • 100
  • [ 16545-68-9 ]
  • [ 157665-52-6 ]
  • C14H17NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With sodium hydride In diethyl ether at 0 - 20℃; for 3h; A2 Synthesis of Compound 2F. To a vial containing Compound 2E (200 mg, 829.14 pmol) was added Et20 (9.12 mL), followed by the careful addition of sodium hydride (39.80 mg, 1.66 mmol) at 0 °C. The reaction was allowed to equilibrate to room temperature, and then stirred for 3 hours at room temperature. The reaction mixture was concentrated onto silica and purified by flash column chromatography provide Compound 2F (0.137 g, 0.493 mmol, 59% yield).
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