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[ CAS No. 15898-26-7 ] {[proInfo.proName]}

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Chemical Structure| 15898-26-7
Chemical Structure| 15898-26-7
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Product Details of [ 15898-26-7 ]

CAS No. :15898-26-7 MDL No. :MFCD00453921
Formula : C13H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNZAIUIEXCYTCY-UHFFFAOYSA-N
M.W : 215.25 Pubchem ID :459078
Synonyms :

Calculated chemistry of [ 15898-26-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.15
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.66
TPSA : 42.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.129 mg/ml ; 0.000601 mol/l
Class : Soluble
Log S (Ali) : -3.19
Solubility : 0.14 mg/ml ; 0.000649 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.0755 mg/ml ; 0.000351 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 15898-26-7 ]

Signal Word:Warning Class:
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#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15898-26-7 ]

* 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 [ 15898-26-7 ]

[ 15898-26-7 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 5044-24-6 ]
  • [ 15898-26-7 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; iodine; magnesium Behandeln des Reaktionsprodukts mit Kohlendioxid;
With diethyl ether; lithium Behandeln des Reaktionsprodukts mit Kohlendioxid;
  • 2
  • [ 150-13-0 ]
  • [ 110-13-4 ]
  • [ 15898-26-7 ]
YieldReaction ConditionsOperation in experiment
99% In isopropyl alcohol for 15h; Heating / reflux; 69b.1 Step 1: 4-(3,5-Dimethyl-1H-pyrazol-1-yl) benzoic acid (252b) [0405] 4-Aminobenzoic acid (251b, 1.5 g, 10.9 MMOL) and hexane-2,5-dione (1.28 mL, 10.9 MMOL) were dissolved in isopropanol (40 mL) and REFLUXED for 15 hours. The solvent was removed under reduced pressure to afford 252b as a white solid (2.35 g, 99% yield NMR: (DMSO) 8 8.02 (d, J=8.6 Hz, 2H), 7.36 (d, J=8.6 Hz, 2H), 5.81 (s, 2H), 1.98 (s, 6H).
96% With zinc tetrafluoroborate In water at 20℃; for 0.166667h;
93% With ionic liquid-supported SiO2*CF3SO3(1-) In ethanol at 20℃; for 0.5h; Green chemistry; Typical procedure in the preparation of pyrroles General procedure: A mixture of amine (0.1 mol), 1,4-diketone (0.1 mol) and ethanol (20 mL) ILCF3SO3(at)SiO2 (0.8 g) were stirred for aspecific time (Table 3) at room temperature. On completion (monitored by GC), the catalyst was recovered by filtration, dried and reused for the next run. The solvent was removedu nder reduced pressure to yield the desired product. The products were identified by 1H NMR, 13C NMR and elemental analysis, and the characterization spectra are provided inthe supporting information
92% With salicylic acid In neat (no solvent) for 0.166667h; Microwave irradiation; 2.1 Procedure for the preparation of 2,5-dimethylpyrroles General procedure: A laboratory microwave oven MW 3100 (LandgrafLaborsysteme HLL GmbH, Langenhagen, Germany)equipped with a magnetic stirrer operating at 2450 MHz was used for synthesis of pyrrole derivatives.In a typical reaction, primary amine (1.0 mmol),hexane-2,5-dione (1.2 mmol) and salicylic acid(0.02 g, 0.15 mmol) were taken in an open vessel and irradiated for an appropriate time and monitored by GC. Water (20 mL) was added to the reaction mixture and stirred for 10 min. The mixture was then extracted by ethyl acetate (2 9 5 mL) and the organic layer was separated and dried over Na2SO4. The solvent wasthen evaporated under reduced pressure to obtain the corresponding product. In those cases where thereaction did not proceed to the completeness, the crudeproduct was passed through a short column of neutralalumina [eluted with ethyl acetate/petroleum ether(3:7)] to give the pure pyrrole 1
90% With diethylenetriaminepentaacetic acid on magnetic Fe3O4 nanoparticles In ethanol; water at 20℃; for 1.25h; General Procedure for Synthesis of Pyrroles in Presence of Fe3O4(at)DTPA General procedure: To a solution of amine (1 mmol) and hexan-2,5-dione (1 mmol) in EtOH-H2O (2 ml, 1:1) at room temperature was added catalyst (40 mg ~4 mol%). The mixture was stirred at this temperature for the required period of time (Table 3). The reaction was monitored using TLC (silica gel, 3:1 n-hexane-acetone). After completion of the reaction, 10 ml of ethanol was added, and the catalyst was removed using an external magnet. Concentration gave the crude product as a solid. The crude product was purified by recrystallization from ethanol to afford pure product. For the compounds that were oils (3h, 3m, 3o), identification was made by matching 1H-NMR and 13C-NMR values withthose in the literature.37,40
90% With oxalic acid In ethanol at 60℃; for 0.5h; Green chemistry; General procedure forthepreparation of2,5-dimethylpyrroles General procedure: In a typical reaction, primary aromatic amine (1 mmol), hexane-2,5-dione (1.2 mmol) and a naturally occurring organic acid (0.2 mmol) were dissolved in ethanol (2mL) and stirred at 60°C for an appropriate reaction time. After completion of the reaction (monitored by GC), water (2×10mL) was added to the reaction mixture in order to remove the catalyst. The obtained solution was extracted by ethyl acetate (2×5mL), and the organic layer was separated and dried over Na2SO4. The separated organic phase was evaporated under reduced pressure to give the corresponding pyrrole. In cases where the reaction did not proceed to completeness, crude product was purifed by recrystallization (in ethanol) or by column chromatography [ethyl acetate/petroleum ether (3:7)] to give the pure product 1. All products 1ar are known compounds, and their structures were confrmed by melting point and/or identifed by comparison of their GC and GC/MS with those of authentic samples reported in our previous papers.
83% With acetic acid at 150℃; for 0.166667h; Microwave irradiation;
82% With L-Tartaric acid; N,N'-Dimethylurea at 70℃; for 0.25h; Green chemistry;
75% With silica sulfuric acid at 20℃; for 0.5h; Neat (no solvent); Grinding;
75% With sodium dodecyl-sulfate In water at 20℃; for 1h; Micellar solution; Green chemistry;
75% With sulfamic acid heterogenized on functionalized magnetic Fe3O4 nanoparticles with diaminoglyoxime In ethanol; water at 20℃; for 1.5h;
70% With chloroamine-T In acetonitrile at 20℃; for 4h;
70% With trichloroisocyanuric acid In acetonitrile at 20℃; for 4h; 4.1. General procedure for the synthesis of pyrroles with TCCA General procedure: To a solution of amine 1 (1 mmol) and 2,5-hexanedione 2 (1 mmol) in CH3CN (3 ml), TCCA (0.02 mmol) was added at rt. The mixture was allowed to stir at this temperature for the period time specified in Table 1. The reaction was monitored by thin layer chromatography (TLC)(3:1 n-hexane/acetone). After completion of the reaction, the solvent was evaporated. Then,CH2Cl2 (10 ml) was added, and the catalyst was removed by filtration. Evaporation of the solventunder reduced pressure gave the products. Further purification was achieved by TLC usingn-hexane/acetone (70:30) as the solvent system to afford the pyrroles.
68% With acetic acid at 150℃; for 4h; Cooling with ice;
64% With acetic acid for 0.5h; Reflux; 4-(2,5-Dimethyl-1H-pyrrol-2-yl) benzoic acid (2) Acetonyl acetone (13.69g, 0.12 mol) was added to p-amino benzoic acid (13.72 g, 0.1 mol) in gl acetic acid (100 mL) and mixture was heated at reflux for 30 min. The reaction mixture was poured into ice cold water; precipitated solid was filtered and dried. Solid crude product was recrystallized from ethanol and obtained as brown crystals in 64% yield. M.P. 204-208°. IR (KBr): umax, cm-1 : 3371 (OH), 2299 (ArH) and 1683 (C=O). 1H NMR (400 MHz, DMSO-d6): d (ppm):1.98 (s, 6H, 2CH3), 5.79 (s, 2H, pyrrole-C3 and C4-H),7.33 (d, 2H, phenyl-C3 and C5-H), 8.07 (d, 2H, phenyl-C2 and C6-H), 12.92 (br, s, 1H, COOH). 13C NMR (100 MHz, DMSO-d6): 13.09 (2CH3 at pyrrole-C2 and C5),106.69 (pyrrole-C3 and C4), 128.29 (phenyl-C3 and C5),128.62 (phenyl-C2), 131.18 (phenyl-C1 and C4), 143.99(phenyl-C6), (171.42) (C=O). EIMS (m/z) : 215 (M+).
60% With (1,3-phenylenedisulfonyl)dichlorimidous chloride In acetonitrile at 20℃; for 0.833333h;
With benzene Entfernen des entstehenden Wassers;
With hydrogenchloride
With toluene Entfernen des entstehenden Wassers;
With acetic acid

Reference: [1]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2005/30704, 2005, A1 Location in patent: Page/Page column 230-231
[2]Ranu, Brindaban C.; Ghosh, Sudip; Das, Arijit [Mendeleev Communications, 2006, vol. 16, # 4, p. 220 - 221]
[3]Liu, Yang; Hu, Yu Lin [Journal of the Iranian Chemical Society, 2018, vol. 15, # 5, p. 1033 - 1040]
[4]Aghapoor, Kioumars; Mohsenzadeh, Farshid; Darabi, Hossein Reza; Sayahi, Hani [Journal of Chemical Sciences, 2021, vol. 133, # 2]
[5]Hemmati, Saba; Mohammadi, Pourya; Sedrpoushan, Alireza; Maleki, Behrooz [Organic Preparations and Procedures International, 2018, vol. 50, # 5, p. 465 - 481]
[6]Mohsenzadeh, Farshid; Darabi, Hossein Reza; Alivand, Mahsa; Aghapoor, Kioumars; Balavar, Yadollah [Research on Chemical Intermediates, 2020, vol. 46, # 12, p. 5255 - 5262]
[7]Location in patent: experimental part Liu, Kun; Lu, Hong; Hou, Ling; Qi, Zhi; Teixeira, Cátia; Barbault, Florent; Fan, Bo-Tao; Liu, Shuwen; Jiang, Shibo; Xie, Lan [Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7843 - 7854]
[8]Alvi, Shakeel; Ali, Rashid [Organic and Biomolecular Chemistry, 2021, vol. 19, # 44, p. 9732 - 9745]
[9]Location in patent: scheme or table Veisi, Hojat [Tetrahedron Letters, 2010, vol. 51, # 16, p. 2109 - 2114]
[10]Veisi, Hojat; Azadbakht, Reza; Ezadifar, Mehdi; Hemmati, Saba [Journal of Heterocyclic Chemistry, 2013, vol. 50, # SUPPL.1, p. E241-E246]
[11]Veisi, Hojat; Mohammadi, Pourya; Gholami, Javad [Applied Organometallic Chemistry, 2014, vol. 28, # 12, p. 868 - 873]
[12]Veisi, Hojat; Ataee, Meral; Fatolahi, Leila; Lotfi, Shahram [Letters in Organic Chemistry, 2013, vol. 10, # 2, p. 111 - 117]
[13]Hemmati, Saba; Mojtahedi, Mohammad Majid; Abaee, Mohammad Saeed; Vafajoo, Zahra; Saremi, Shokufe Ghahri; Noroozi, Mohammad; Sedrpoushan, Alireza; Ataee, Meral [Journal of Sulfur Chemistry, 2013, vol. 34, # 4, p. 347 - 357]
[14]Zhu, Weixing; Groh, Matthias; Haupenthal, Jörg; Hartmann, Rolf W. [Chemistry - A European Journal, 2013, vol. 19, # 26, p. 8397 - 8400]
[15]Hallikeri; Joshi, Shrinivas D.; Kumar, Devendra; Kulkarni [Indian Journal of Heterocyclic Chemistry, 2015, vol. 25, # 1, p. 31 - 36]
[16]Location in patent: experimental part Ghorbani-Vaghei, Ramin; Veisi, Hojat [South African Journal of Chemistry, 2009, vol. 62, p. 33 - 38]
[17]Bishop [Journal of the American Chemical Society, 1945, vol. 67, p. 2261]
[18]Hazlewood et al. [Journal and Proceedings - Royal Society of New South Wales, 1937, vol. 71, p. 92,101]
[19]Bishop [Journal of the American Chemical Society, 1945, vol. 67, p. 2261]
[20]Raynaud et al. [Annales de l'Institut Pasteur, 1957, vol. 92, p. 618,622]
YieldReaction ConditionsOperation in experiment
4-Aminobenzoesaeure, Acetonylaceton;
Acetylaceton, p-Aminobenzoesaeure;
Entspr. Dion, Aminoverb.;
entspr. Dion, entspr. Amin;
Hexan-2,5-dion, p-Aminobenzoesaeure;
Entspr. Dicarbonylverb., Amin;

  • 4
  • [ 110-13-4 ]
  • [ 15898-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: lithium; diethyl ether / Behandeln des Reaktionsprodukts mit Kohlendioxid
  • 5
  • [ 106-40-1 ]
  • [ 15898-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: lithium; diethyl ether / Behandeln des Reaktionsprodukts mit Kohlendioxid
  • 6
  • [ 15898-26-7 ]
  • [ 51207-66-0 ]
  • [4-(2,5-dimethyl-pyrrol-1-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With N-cyclohexanecarbodiimide-N'-propyloxymethyl polystyrene resin In dichloromethane; N,N-dimethyl-formamide at 20℃; 32 [4-(2,5-Dimethyl-pyrrol-1-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone Procedure R: 151mg of 4-(2,5-dimethyl-pyrrol-l-yl)-benzoic acid (CAS 15898-26-7) (0.7mmol), 154mg of (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (l.0 mmol) and 720mg of PS-carbodiimide (l.0 mmol, mmol/g=1.32) are placed into 7mL vial with 5.0mL of 5% DMF in dichloromethane. The vial is capped and shaken at room temperature for overnight. The reaction mixture is filtered and washed by CH2CI2. The filtrate is concentrated under N2 gas. The crude product is applied to silica-gel column chromatography (CH2C12 : 2M NH3 in MeOH = 40:1) to give the product. 68.2mg. Yield 28%. MS (ES+): 352(M+H)+.
  • 7
  • [ 15898-26-7 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-(1-(4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)ethylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / Reflux 2: hydrazine hydrate / Reflux 3: acetic acid / ethanol / Reflux
  • 8
  • [ 15898-26-7 ]
  • [ 26165-67-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / Reflux 2: hydrazine hydrate / Reflux
  • 9
  • [ 15898-26-7 ]
  • N'-(1-(4-(1H-pyrrol-1-yl)phenyl)ethylidene)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / Reflux 2: hydrazine hydrate / Reflux 3: acetic acid / ethanol / Reflux
  • 10
  • [ 15898-26-7 ]
  • [ 64-17-5 ]
  • [ 5159-70-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Reflux; 4.2. General procedure for the synthesis of ethyl aromatic esters (8a-s) 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.
  • 11
  • [ 15898-26-7 ]
  • [ 62-53-3 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-phenylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform. 3a: 4-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-phenylbenzamide IR (KBr): 3314 (amide NH), 2917 (ArH) and 1655(amide C=O). 1H NMR (400 MHz, DMSO-d6): 2.04 (s,6H, 2CH3), 5.93 (s, 2H, pyrrole-C3 and C4), 7.15-7.98 (m, 9H, bridge phenyl-C2, C3, C5 and C6, phenyl-C2,C3, C4, C5 and C6), 8.03 (s, 1H, amide NH). 13C NMR (100 MHz, DMSO-d6): 13.07 (2CH3 at pyrrole-C2 andC5), 106.46 (pyrrole-C3 and C4), 120.27 (pyrrole-C2 andC5), 124.78 (phenyl-C2 and C6), 128.48 (phenyl-C4),127.98 (bridge phenyl-C2 and C6), 128.62 (phenyl-C3and C5), 129.14 (bridge phenyl-C3 and C5), 137.71(bridge phenyl-C1), 142.14 (bridge phenyl-C4), 165.01(C=O); EIMS (m/z): 290 (M+).
  • 12
  • [ 15898-26-7 ]
  • [ 106-40-1 ]
  • N-(4-bromophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl) benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 13
  • [ 15898-26-7 ]
  • [ 106-47-8 ]
  • N-(4-chlorophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 14
  • [ 15898-26-7 ]
  • [ 106-49-0 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-methylphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 15
  • [ 15898-26-7 ]
  • [ 104-94-9 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-methoxyphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 16
  • [ 582-33-2 ]
  • [ 15898-26-7 ]
  • ethyl 3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl]amino}benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 17
  • [ 15898-26-7 ]
  • [ 100-01-6 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-nitrophenyl) benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 18
  • [ 15898-26-7 ]
  • [ 95-51-2 ]
  • N-(2-chlorophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 19
  • [ 15898-26-7 ]
  • [ 615-36-1 ]
  • N-(2-bromophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 20
  • [ 15898-26-7 ]
  • [ 554-00-7 ]
  • N-(2,4-dichlorophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 5h; Substituted 4-(2,5-dimethyl-1H-pyrrol-1-yl)-Nphenylbenzamides (3a-j) : General procedure General procedure: Appropriate aromatic amines (0.16 g, 0.0018 mol) and 4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (0.43 g, 0.0019 mol) were dissolved in dry DMF, HBTU (0.87g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 5 hr at 23°. The reaction mixture was quenched by brine. The resulting mixture was extracted with ethyl acetate (3X 50 mL). The ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate solution followed by brine and then solvent was evaporated to dryness. Crude product was recrystallized from chloroform.
  • 21
  • [ 2010-06-2 ]
  • [ 15898-26-7 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-phenyl-1,3-thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 22
  • [ 2103-94-8 ]
  • [ 15898-26-7 ]
  • N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 23
  • [ 2103-99-3 ]
  • [ 15898-26-7 ]
  • N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 24
  • [ 15898-26-7 ]
  • [ 2104-09-8 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 25
  • [ 2104-04-3 ]
  • [ 15898-26-7 ]
  • N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 26
  • [ 105512-81-0 ]
  • [ 15898-26-7 ]
  • N-[4-(3-bromophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-4-(4-substituted phenyl)thiazole-2-yl-4-(1H-pyrrol-1yl)bezamides (3a-e)/N-4-(4-substituted phenyl)thiazol-2-yl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides(4a-f) General procedure: The 2-amino-4-(4-substituted phenyl)thiazoles (2a-f) (Pattanet al. 2009) (0.0018 mol) and 4-(1H-pyrrolyl-1-yl)benzoicacid (9a) (Joshi et al. 2018)/4-(2,5-dimethyl-1Hpyrrolyl-1-yl)benzoic acid (9b) (Joshi et al. 2008)(0.0019 mol) were dissolved, respectively in 50 mL of dry dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixturesand stirred for 24-30 h at ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith a saturated sodium bicarbonate solution followed byNaCl. The organic layer was dried over anhydrous sodiumsulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by column chromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (3a-e) and(4-f) (Scheme 1).
  • 27
  • [ 61954-82-3 ]
  • [ 15898-26-7 ]
  • N-(5-bromo-4-phenyl-1,3-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides (6a-e)/N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(1Hpyrrol-1-yl)benzamides (7a-b) General procedure: The 4-(4-substituted phenyl)-5-bromo-2-aminothiazoles (5a-e)(0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid(9b)/4(1H-pyrrol-1-yl)benzoic acid (9a) (0.0019mol) weredissolved, respectively in 50mL of dry dimethyl formamide.HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 mL, 0.0053mol)were then added to the above mixtures and stirred for 24-30 hat room temperature. The reaction was quenched by addingNaCl solution and the mixture was extracted with ethyl acetate(3 × 50mL). The combined ethyl acetate layer was washedwith 1N HCl and with a saturated sodium bicarbonate solutionfollowed by NaCl. The organic layer was dried over anhydroussodium sulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by columnchromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (6a-e) and(7a-b) (Scheme 1). N-(5-bromo-4-phenyl-1,3-thiazol-2-yl)-4-(2,5-dimethyl-1Hpyrrol-1-yl)benzamide (6a) Compound 6a was obtained as red solid (yield 86%). m.p.108-110 °C; FTIR (KBr): 3298, 3178, 1708, 1607 cm-1; 1HNMR (400MHz, DMSO-d6) δ ppm: 12.10 (1H, s, NH),8.08 (2H, d, J = 8.4 Hz, H-17, H-21), 7.91 (2H, d, J =3.7 Hz, H-18, H-20), 7.82 (2H, d, J = 6.7 Hz, H-10, H-14),7.78-7.20 (3H, m, H-11, H-12, H-13), 5.77 (2H, s, H-24, H-25), 2.00 (6H, s, H-27, H-28-diCH3); 13C NMR (75MHz,DMSO-d6) δ ppm: 168.19 (CO, C-8), 166.98 (C-2), 152.30(C-4), 143.20 (C-16), 134.93 12 (C-12), 133.75 (C-9),130.18 (C-19), 128.44 (CH, C-10, C-14), 128.15 (CH, C-17, C-21), 127.78 (CH, C-11, C-13), 127.15 (CH, C-18, C-20), 125.53 (CH, C-23, C-26), 108.69 (CH, C-24, C-25),101.47 (C-5), 12.55 (C-27, C-28-diCH3); MS (ESI): m/z =found 452.47 [M+], 454.10 [M + 2] (calcd. 452.37); anal.calcd. For C22H18N3OSBr: C, 58.41; H, 4.01; N, 9.29;Found: C, 58.69; H, 4.33; N, 9.52.
  • 28
  • [ 15898-26-7 ]
  • [ 98592-19-9 ]
  • N-[5-bromo-4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides (6a-e)/N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(1Hpyrrol-1-yl)benzamides (7a-b) General procedure: The 4-(4-substituted phenyl)-5-bromo-2-aminothiazoles (5a-e)(0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid(9b)/4(1H-pyrrol-1-yl)benzoic acid (9a) (0.0019mol) weredissolved, respectively in 50mL of dry dimethyl formamide.HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 mL, 0.0053mol)were then added to the above mixtures and stirred for 24-30 hat room temperature. The reaction was quenched by addingNaCl solution and the mixture was extracted with ethyl acetate(3 × 50mL). The combined ethyl acetate layer was washedwith 1N HCl and with a saturated sodium bicarbonate solutionfollowed by NaCl. The organic layer was dried over anhydroussodium sulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by columnchromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (6a-e) and(7a-b) (Scheme 1).
  • 29
  • [ 15898-26-7 ]
  • 5-bromo-4-(4-chlorophenyl)thiazol-2-amine [ No CAS ]
  • N-[5-bromo-4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides (6a-e)/N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(1Hpyrrol-1-yl)benzamides (7a-b) General procedure: The 4-(4-substituted phenyl)-5-bromo-2-aminothiazoles (5a-e)(0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid(9b)/4(1H-pyrrol-1-yl)benzoic acid (9a) (0.0019mol) weredissolved, respectively in 50mL of dry dimethyl formamide.HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 mL, 0.0053mol)were then added to the above mixtures and stirred for 24-30 hat room temperature. The reaction was quenched by addingNaCl solution and the mixture was extracted with ethyl acetate(3 × 50mL). The combined ethyl acetate layer was washedwith 1N HCl and with a saturated sodium bicarbonate solutionfollowed by NaCl. The organic layer was dried over anhydroussodium sulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by columnchromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (6a-e) and(7a-b) (Scheme 1).
  • 30
  • [ 15898-26-7 ]
  • 5-Bromo-4-(4-nitro-phenyl)-thiazol-2-ylamine [ No CAS ]
  • N-[5-bromo-4-(4-nitrophenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides (6a-e)/N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(1Hpyrrol-1-yl)benzamides (7a-b) General procedure: The 4-(4-substituted phenyl)-5-bromo-2-aminothiazoles (5a-e)(0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid(9b)/4(1H-pyrrol-1-yl)benzoic acid (9a) (0.0019mol) weredissolved, respectively in 50mL of dry dimethyl formamide.HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 mL, 0.0053mol)were then added to the above mixtures and stirred for 24-30 hat room temperature. The reaction was quenched by addingNaCl solution and the mixture was extracted with ethyl acetate(3 × 50mL). The combined ethyl acetate layer was washedwith 1N HCl and with a saturated sodium bicarbonate solutionfollowed by NaCl. The organic layer was dried over anhydroussodium sulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by columnchromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (6a-e) and(7a-b) (Scheme 1).
  • 31
  • [ 15898-26-7 ]
  • [ 98946-76-0 ]
  • N-[5-bromo-4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamides (6a-e)/N-(5-bromo-4-(4-substitutedphenyl)-thiazol-2-yl)-4-(1Hpyrrol-1-yl)benzamides (7a-b) General procedure: The 4-(4-substituted phenyl)-5-bromo-2-aminothiazoles (5a-e)(0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid(9b)/4(1H-pyrrol-1-yl)benzoic acid (9a) (0.0019mol) weredissolved, respectively in 50mL of dry dimethyl formamide.HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 mL, 0.0053mol)were then added to the above mixtures and stirred for 24-30 hat room temperature. The reaction was quenched by addingNaCl solution and the mixture was extracted with ethyl acetate(3 × 50mL). The combined ethyl acetate layer was washedwith 1N HCl and with a saturated sodium bicarbonate solutionfollowed by NaCl. The organic layer was dried over anhydroussodium sulfate and concentrated using a rotary flash evaporator.Thus obtained residue was dried and purified by columnchromatography using petroleum ether:ethyl acetate (6:4)mixture as the eluent to afford the compounds (6a-e) and(7a-b) (Scheme 1).
  • 32
  • [ 15898-26-7 ]
  • [ 100-46-9 ]
  • N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(substituted phenyl)benzamides (11a-d) General procedure: Different aromatic amines (0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9b) (0.0019 mol)were dissolved, respectively, in 50 mL of dry dimethylformamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixtureand stirred for 24-30 h at the ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith the saturated sodium bicarbonate followed by NaClsolution. The organic layer was dried over an anhydroussodium sulfate and concentrated using rotary flash evaporator.Thus obtained residue was dried and purified bycolumn chromatography using petroleum ether:ethyl acetate(6:4) mixture as the eluent to afford the desired compounds(10) and (11a-d) (Scheme 2). N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10) Compound 10 was obtained as yellow solid (yield 90%). m.p.158-160 °C; FTIR (KBr): 3299, 2921, 1635, 1607 cm-1; 1HNMR (400MHz, DMSO-d6) δ ppm: 9.18 (1H, s, NH), 8.03(2H, d, J=8.4Hz, H-7, H-11), 7.39 (2H, d, J=8.4 Hz, H-8,H-10), 7.34-7.25 (3H, m, H-20, H-21, H-22), 7.24 (2H, d, J=4.8Hz, H-19, H-23), 5.82 (2H, s, H-3, H-4), 4.52 (2 H, d, J=6.0Hz, CH2), 1.98 (6H, s, H-12, H-13-diCH3); 13C NMR(75MHz, DMSO-d6) δ ppm: 166.15 (CO, C-15), 141.29 (C-6), 138.98 (C-18), 133.76 (C-9), 128.76 (CH, C-7, C-11),128.29 (CH, C-19, C-23), 128.01 (CH, C-8, C-10), 127.67(CH, C-20, C-22), 126.25 (C-21), 122.25 (CH, C-2, C-5),106.87 (CH, C-3, C4), 43.15 (C-17, CH2), 13.32 (C-12, C-13,Pyrrole-diCH3); MS (ESI): m/z=found 303.46 [M-1] (calcd.304.39); anal. calcd. For C20H20N2O: C, 78.92; H, 6.62; N,9.20; Found: C, 79.04; H, 6.87; N, 9.44.
  • 33
  • [ 15898-26-7 ]
  • [ 536-90-3 ]
  • 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(3-methoxyphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(substituted phenyl)benzamides (11a-d) General procedure: Different aromatic amines (0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9b) (0.0019 mol)were dissolved, respectively, in 50 mL of dry dimethylformamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixtureand stirred for 24-30 h at the ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith the saturated sodium bicarbonate followed by NaClsolution. The organic layer was dried over an anhydroussodium sulfate and concentrated using rotary flash evaporator.Thus obtained residue was dried and purified bycolumn chromatography using petroleum ether:ethyl acetate(6:4) mixture as the eluent to afford the desired compounds(10) and (11a-d) (Scheme 2).
  • 34
  • [ 15898-26-7 ]
  • [ 608-31-1 ]
  • N-(2,6-dichlorophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(substituted phenyl)benzamides (11a-d) General procedure: Different aromatic amines (0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9b) (0.0019 mol)were dissolved, respectively, in 50 mL of dry dimethylformamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixtureand stirred for 24-30 h at the ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith the saturated sodium bicarbonate followed by NaClsolution. The organic layer was dried over an anhydroussodium sulfate and concentrated using rotary flash evaporator.Thus obtained residue was dried and purified bycolumn chromatography using petroleum ether:ethyl acetate(6:4) mixture as the eluent to afford the desired compounds(10) and (11a-d) (Scheme 2).
  • 35
  • [ 15898-26-7 ]
  • [ 106-50-3 ]
  • N-(4-aminophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(substituted phenyl)benzamides (11a-d) General procedure: Different aromatic amines (0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9b) (0.0019 mol)were dissolved, respectively, in 50 mL of dry dimethylformamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixtureand stirred for 24-30 h at the ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith the saturated sodium bicarbonate followed by NaClsolution. The organic layer was dried over an anhydroussodium sulfate and concentrated using rotary flash evaporator.Thus obtained residue was dried and purified bycolumn chromatography using petroleum ether:ethyl acetate(6:4) mixture as the eluent to afford the desired compounds(10) and (11a-d) (Scheme 2).
  • 36
  • [ 15898-26-7 ]
  • [ 95-54-5 ]
  • N-(2-aminophenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-benzyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide (10)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(substituted phenyl)benzamides (11a-d) General procedure: Different aromatic amines (0.0018 mol) and 4-(2, 5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9b) (0.0019 mol)were dissolved, respectively, in 50 mL of dry dimethylformamide. HBTU (0.87 g, 0.0023 mol) and DIEA(0.93 mL, 0.0053 mol) were then added to the above mixtureand stirred for 24-30 h at the ambient temperature. Thereaction was quenched by adding NaCl solution and themixture was extracted with ethyl acetate (3 × 50 mL). Thecombined ethyl acetate layer was washed with 1 N HCl andwith the saturated sodium bicarbonate followed by NaClsolution. The organic layer was dried over an anhydroussodium sulfate and concentrated using rotary flash evaporator.Thus obtained residue was dried and purified bycolumn chromatography using petroleum ether:ethyl acetate(6:4) mixture as the eluent to afford the desired compounds(10) and (11a-d) (Scheme 2).
  • 37
  • [ 15898-26-7 ]
  • [ 19837-86-6 ]
  • N-(4-(N-(2-bromophenyl)sulfamoyl)phenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10℃; for 24h; General procedure for the synthesis ofN-(4-(Nsubstituted-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N-substituted-phenylsulfamoyl)phenyl)benzamides 10(a-b) General procedure: P-amino-N-substituted-phenylbenzenesulfonamides4(a-e) (0.0018 mol) and 4-(1H-pyrrol-1-yl)benzoicacid (7)/4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (9) (0.39 g, 0.0019 mol) were dissolved, respectively,in 30 mL of dry N’, N’-Dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 24 h at 10°C. The reactionwas quenched by adding brine. The resulting mixturewas extracted with ethyl acetate (3 × 50 ml). Thecombined ethyl acetate layer was washed with 1NHCl then with saturated sodium bicarbonate, followedby brine. The organic layer was dried over anhydroussodium sulfate to get titled compounds N-(4-(Nsubstituted-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N-substituted-phenylsulfamoyl)phenyl)benzamides10(a-b), respectively. The obtained compounds werepurified by column chromatography using ethylacetate: petroleum ether (6:4) as a solvent and iodinevapors as visualizing agent.
  • 38
  • [ 15898-26-7 ]
  • [ 19837-85-5 ]
  • N-(4-(N-(2-chlorophenyl)sulfamoyl)phenyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10℃; for 24h; General procedure for the synthesis ofN-(4-(Nsubstituted-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N-substituted-phenylsulfamoyl)phenyl)benzamides 10(a-b) General procedure: P-amino-N-substituted-phenylbenzenesulfonamides4(a-e) (0.0018 mol) and 4-(1H-pyrrol-1-yl)benzoicacid (7)/4-(2,5-dimethyl-1H-pyrrol-1-yl) benzoic acid (9) (0.39 g, 0.0019 mol) were dissolved, respectively,in 30 mL of dry N’, N’-Dimethyl formamide. HBTU (0.87 g, 0.0023 mol) and DIEA (0.93 ml, 0.0053 mol) were added and stirred for 24 h at 10°C. The reactionwas quenched by adding brine. The resulting mixturewas extracted with ethyl acetate (3 × 50 ml). Thecombined ethyl acetate layer was washed with 1NHCl then with saturated sodium bicarbonate, followedby brine. The organic layer was dried over anhydroussodium sulfate to get titled compounds N-(4-(Nsubstituted-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N-substituted-phenylsulfamoyl)phenyl)benzamides10(a-b), respectively. The obtained compounds werepurified by column chromatography using ethylacetate: petroleum ether (6:4) as a solvent and iodinevapors as visualizing agent.
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