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Product Details of [ 120122-47-6 ]

CAS No. :120122-47-6 MDL No. :MFCD03789117
Formula : C7H5Cl3N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WASYNLWEPOHNBM-UHFFFAOYSA-N
M.W : 271.49 Pubchem ID :2759966
Synonyms :

Safety of [ 120122-47-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:1759
Hazard Statements:H314 Packing Group:
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Application In Synthesis of [ 120122-47-6 ]

* 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 [ 120122-47-6 ]

[ 120122-47-6 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 21898-65-7 ]
  • [ 53391-42-7 ]
  • [ 120122-47-6 ]
YieldReaction ConditionsOperation in experiment
1: 69% 2: 18% With nitric acid In acetic anhydride for 2h; Ambient temperature;
18% With nitric acid; acetic anhydride at 20℃; for 3h;
  • 2
  • [ 78486-14-3 ]
  • [ 120122-47-6 ]
  • [ 65361-31-1 ]
YieldReaction ConditionsOperation in experiment
87% In N,N-dimethyl-formamide from 0 degC to room t.;
65.5% In dichloromethane at 20℃; for 1h; The trichloroacetyl pyrrole (11.44 g, 0.051 mol) and the pyrrole amine (13.9 g, 0.051 mol) were dissolved in anhydrous DCM (50 mL) and allowed to stir for 1 h at room temperature. A precipitate was formed and collected by vacuum filtration. The solid was resuspended in EtOAc and concentrated under reduced pressure to yield the nitro-dipyrrole compound as a yellow solid (13.58 g, 65.5%). 1H-NMR (DMSO-d6) (400 MHz) δ 8.26 (s, 1H, NH-amide.), 8.16 (d, J = 1.92 Hz, 1H, py), 7.56 (d, J = 1.99 Hz, 1H, py), 7.19 (d, J = 1.82 Hz, 1H, py), 6.81 (d, J = 1.87 Hz, 1H, py), 3.94 (s, 3H, N-CH3 py), 3.80 (s, 3H, N-CH3 py), 3.23-3.14 (m, 2H, CH2 aliphatic chain), 2.26 (t, J = 7.09 Hz, 2H, CH2 aliphatic chain), 2.15 (s, 6H, N(CH3)2 aliphatic chain), 1.61 (p, J = 7.04 Hz, 2H, CH2 aliphatic chain). 13C-NMR (CDCl3) (400MHz) δ 160.9, 156.7, 133.6, 128.0, 126.2, 123.2, 121.1, 117.7, 107.4, 103.7, 56.8, 44.9, 37.3, 36.9, 35.8, 26.9. MS m/z (ES+) (relative intensity) 377.55 (M+1). HRMS [M+] calculated for C17H24N6O4 m/z 377.1859, found 376.1831.
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
In N,N-dimethyl-formamide at 20℃; for 18h;
1.25 g In N,N-dimethyl-formamide at 0 - 20℃;
In tetrahydrofuran at 20℃;
1.746 g In N,N-dimethyl-formamide at 0℃; for 16h; Inert atmosphere;
3 The methyl ester conjugate 40, prepared in Example 2, was HYDROLYZED with base to form the carboxylic acid 41. N,N-dimethylpropanediamine 42 was coupled with 32 using HALOFORM conditions to give 43, which upon HYDROGENATION followed by further coupling with 32 afforded 45. HYDROGENATION of 45 and amide coupling with the intermediate 41 resulted in the conjugate 47. Further HYDROGENATION of 47 on PD-C and ammonium formate as the hydrogen source afforded 48, THE"SECO"FORM of the final conjugate, ready to be used for biological studies. See Figure 5.

  • 3
  • [ 120122-47-6 ]
  • [ 109-55-7 ]
  • [ 65361-30-0 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran for 0.5h; Ambient temperature;
99% In tetrahydrofuran at 20℃;
97% at 20℃; for 12h;
96% In tetrahydrofuran at 20℃; for 2h;
96% In tetrahydrofuran at 20℃; for 1h;
95% In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
88% In tetrahydrofuran at 20℃; for 6h;
87% In tetrahydrofuran for 2h; 3-Dimethylamino-1-propylamine (7 mL, 0.055 mol) was added to a mechanically stirred solution of 4-nitro-2-(trichloroacetyl)-1-methylpyrrole (15 g, 0.055 mol) in THF (20 mL). The reaction mixture was allowed to stir for 2 hours and subsequently diluted with hexane in order to precipitate the product. The precipitate was collected by vacuum filtration to provide N-(3-(dimethylamino)propyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide as a cream coloured crystalline solid (13 g, 87%). 1H-NMR (CDCl3) (400 MHz) δ 8.66 (s, 1H, NH-amide), 7.51 (d, J = 1.81 Hz, 1H, py), 6.91 (d, J = 1.85 Hz, 1H, py), 4.0 (s, 3H, N-CH3 py), 3.61-3.36 (m, 2H, CH2 aliphatic chain), 2.59-2.43 (m, 2H, CH2 aliphatic chain), 2.31 (s, 6H, N(CH3)2 aliphatic chain), 1.81-1.61 (m, 2H, CH2 aliphatic chain). 13C-NMR (CDCl3) (400MHz) δ 159.7, 134.4, 126.5, 125.7, 105.9, 59.2, 44.9, 40.0, 37.3, 24.2. MS m/z (ES+) (relative intensity) 255.15 (M+1).
86% In tetrahydrofuran at 0 - 20℃; for 0.0291667h; Inert atmosphere;
84% In tetrahydrofuran at 0 - 20℃;
84% In tetrahydrofuran at 0 - 20℃; for 1h; 4 The compound 11 (25 g, 92 mmol) disclosed in the article (Nishiwaki, E.; Tanaka, S.; Lee, H.; Shibuya, M. Heterocycles 1988, 8, 1945-1952) was added dropwise to THF (10ml) dissolving3-dimethylaminopropylamine (12.6g, 101 mmol) at 0°C. After being heated to a room temperature, the resulting solution was stirred for one hour, and the solvent was distilled out. Re-crystallization of the residue with methanol gave the compound 12 (19.6 g, 84%). 1HNMR (DMSO-d6) δ 1.6(t,J=7.1Hz), 2.1(6H,s),2.2(2H,t;J=7.1Hz),3.2(2H,q,J=7.1Hz) 3.9(3H,s),7.9(1H,s),8.1(1H,s),8.4(1H,t,J=5.5Hz).
70%
66% In dichloromethane at 0 - 20℃; for 1h;
In tetrahydrofuran at 20℃; for 3h;
In ethyl acetate at 20℃; for 12h; Inert atmosphere;
In dichloromethane Inert atmosphere;
3 The methyl ester conjugate 40, prepared in Example 2, was HYDROLYZED with base to form the carboxylic acid 41. N,N-dimethylpropanediamine 42 was coupled with 32 using HALOFORM conditions to give 43, which upon HYDROGENATION followed by further coupling with 32 afforded 45. HYDROGENATION of 45 and amide coupling with the intermediate 41 resulted in the conjugate 47. Further HYDROGENATION of 47 on PD-C and ammonium formate as the hydrogen source afforded 48, THE"SECO"FORM of the final conjugate, ready to be used for biological studies. See Figure 5.

Reference: [1]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[2]Rahman, Khondaker M.; Jackson, Paul J. M.; James, Colin H.; Basu, B. Piku; Hartley, John A.; De La Fuente, Maria; Schatzlein, Andreas; Robson, Mathew; Pedley, R. Barbara; Pepper, Chris; Fox, Keith R.; Howard, Philip W.; Thurston, David E. [Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2911 - 2935]
[3]Bando, Toshikazu; Narita, Akihiko; Saito, Isao; Sugiyama, Hiroshi [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3471 - 3485]
[4]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [European Journal of Organic Chemistry, 2000, # 11, p. 2095 - 2103]
[5]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[6]Location in patent: experimental part Vooturi, Sunil K.; Cheung, Chrissy M.; Rybak, Michael J.; Firestine, Steven M. [Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5020 - 5031]
[7]Rahman, Khondaker M.; Reszka, Anthony P.; Gunaratnam, Mekala; Haider, Shozeb M.; Howard, Philip W.; Fox, Keith R.; Neidle, Stephen; Thurston, David E. [Chemical Communications, 2009, # 27, p. 4097 - 4099]
[8]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[9]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[10]Seio, Kohji; Mizuta, Masahiro; Terada, Takeshi; Sekine, Mitsuo [Journal of Organic Chemistry, 2005, vol. 70, # 25, p. 10311 - 10322]
[11]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - EP1719777, 2006, A1 Location in patent: Page/Page column 17; 20
[12]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1102 - 1107]
[13]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[14]Location in patent: scheme or table Han, Xiaochun; Li, Chun; Mosher, Michael D.; Rider, Kevin C.; Zhou, Peiwen; Crawford, Ronald L.; Fusco, William; Paszczynski, Andrzej; Natale, Nicholas R. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1671 - 1680]
[15]Location in patent: scheme or table Liu, Meng-Chi; Ong, Chi Wi [Tetrahedron, 2009, vol. 65, # 40, p. 8389 - 8392]
[16]Location in patent: scheme or table Ong, Chi Wi; Yang, Ya-Ting; Liu, Meng-Chi; Fox, Keith R.; Liu, Ping Hao; Tung, Hung-Wei [Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1040 - 1046]
[17]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2005/32594, 2005, A2 Location in patent: Page/Page column 5; 29-30
  • 4
  • [ 120122-47-6 ]
  • [ 100-51-6 ]
  • [ 120095-66-1 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride In tetrahydrofuran for 0.75h; Ambient temperature;
87% With sodium hydride In tetrahydrofuran at 0 - 20℃;
  • 5
  • [ 120122-47-6 ]
  • [ 162085-97-4 ]
  • [ 169770-26-7 ]
YieldReaction ConditionsOperation in experiment
75% In chloroform; N,N-dimethyl-formamide
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 14h; Methyl-4-nitro-imidazole-2- carboxylate 40 (5 g, 27 mmol) was dissolved in 1 : 1 mixture of MeOH and EtOAc (150 mL). A slurry of moist 10% PdVC in EtOAc was added and the contents were stirred vigorously under hydrogen (70 psi) for 14 h. The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as green solid. The crude amine without any further purification was taken up in CH3CN (150 mL). Contents were cooled to 0 0C and DIEA (6.9 mL, 37.7 mmol) was added. A solution of 1- methyl-4-nitro-2-trichloroacetylpyrrole 23 (7.6 g, 28.2 mmol) in CH3CN (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature for 14 h, EPO during which solid precipitated out. The reaction mixture was filtered to furnish 42 as yellow solid (5 g, 60%). The filtrate was concentrated and the residue was taken up in MeOH. Et2O was added to furnish a second crop of 42 (1 g, 12%). 1H-NMR (DMSO-d6) 611.14 (s, exch, IH, NH), 8.19 (d, IH, J = 1.2 Hz, Py-CH), 7.80 (d, IH, J = 1.2 Hz, Py-CH), 7.68 (s, IH, Im-CH), 3.96 (s, 3H, CH3), 3.94 (s, 3H, CH3), 3.82 (s, 3H, CH3). 13C-NMR (75 MHz, DMSO-d6) 6158.9 (+, s, CO), 157.4 (+, s, CO), 137.1 (+, s, Im-C2), 134.1 (+, s, Py-C4), 131.2 (+, s, Im-C2), 128.2 (-, d, Py-C5), 125.4 (+, s, Py-C2), 1 15.2 (-, d, Im-C5), 1 10.2 (-, d, Py-C3), 52.0 (-, q, OCH3), 37.9 (-, q, CH3), 35.2 (-, q, CH3). EI-HRMS: m/z calcd for Ci3Hi5N5O5 321.1073; found 321.1094 (M+, 20%), 279.0997 (100%), 194.0830 (72%), 153.0317 (35%).
  • 6
  • [ 67-56-1 ]
  • [ 120122-47-6 ]
  • [ 13138-76-6 ]
YieldReaction ConditionsOperation in experiment
100% at 80℃;
96% With sodium hydride at 20℃; for 1h;
96% Stage #1: methanol; 1-methyl-4-nitro-2-trichloroacetylpyrrole With sodium hydride at 20℃; for 1h; Stage #2: With sulfuric acid In water
89% With dmap
80% at 20℃; for 0.5h; Compound 23 (2.7 g,10 mmol) was dissolved in dry MeOH and a catalytic amount of NaH (100 mg) was added to the solution. After stirring the mixture for 30 min at ambient temperature, the solid present in the suspension was collected by filtration and recrystallized (1PrOH) to afford the title product (80% yield). HRMS: C7H8N2O4 184.0484
80% With dmap at 20℃; for 72h;
80% With dmap at 20℃; for 72h;
47% With sodium methylate for 2h; Ambient temperature;
With dmap at 20℃;
With sodium hydride at 20℃; for 2h; 4 Synthesis of methyl 1 -methyl-4-nitro- 1 H-pyrrole-2-carboxylate A solution of 2,2,2-trichloro- 1 -(1 -methyl-4-nitro- 1 H-pyrrol-2-yl)ethanone (24 g, 87 mmol) in methanol (75 mL) was added dropwise to the suspension of NaH (300 mg) inmethanol (30 mL). The reaction mixture was stirred at room temperature for 2 hr, then the reaction was quenched by addition of concentrated sulfuric acid (0.75 mL). The reaction mixture was then heated to reflux and allowed to slowly cool to room temperature. Product crystallized from reaction mixture as white needles. Product was filtered and dried under vacuum. ‘H NMR (ö, DMSO-d6, ppm) 8.27 (bs, 1H, H-5), 7.31 (bs, 1H, H-3), 3.93, 3.80 (2s,3H ea, Me).

  • 7
  • [ 21898-65-7 ]
  • [ 120122-47-6 ]
YieldReaction ConditionsOperation in experiment
85% With nitric acid; acetic anhydride at -5℃; for 3h;
85% With nitric acid; acetic anhydride In isopropyl alcohol at -40℃;
78% With nitric acid In acetic anhydride at -40 - 20℃; for 1h;
71.6% With nitric acid; acetic anhydride at -40 - 20℃; for 0.5h; Inert atmosphere; Large scale; 3 Synthesis of compound c1 To a 50 L reactor, bl (2.00 Kg, 8.85 mol) and acetic anhydride (10 L) were added, and the temperature was lowered to -40 ° C under nitrogen. Concentrated nitric acid (1.5 L) was added dropwise, and the reaction temperature was lower than 5 ° C for 0.5 h, and then the temperature was naturally raised to room temperature. After HPLC reaction, the reaction of the raw materials was completed, and the temperature was lowered to -20 to -30 °C.10 L of diethyl ether was added to precipitate a solid. Filter by suction to obtain a solid which was beaten with diethyl ether.Got 1.72kgShame white solid (c1, yield: 71.6%, purity 99.7%)
70% With nitric acid; acetic anhydride at -25 - 0℃; for 0.5h;
69% With nitric acid; acetic anhydride at -40 - 20℃; Inert atmosphere;
69% With nitric acid; acetic anhydride at -40 - 20℃; for 16.5h;
67% With nitric acid; acetic anhydride at -20 - 20℃; 2.A 1-Methyl-4-nitro-2-trichloroacetyl-1H-pyrrole 2.12 g (9.34 mmol) of 1-methyl-2-trichloroacetyl-1H-pyrrole are dissolved in 9.5 ml of acetic anhydride and cooled to -20° C., and 0.43 ml (9.34 mmol) of nitric acid is added. The mixture is slowly warmed to RT and stirred at RT for 1 h. The reaction mixture is poured into 95 g of ice and stirred vigorously for 2.5 h (initially oily deposit then crystallization). The precipitate is filtered off with suction, triturated with 20 ml of methanol, filtered and dried under reduced pressure overnight. To remove the regioisomers, which are also formed, the product is triturated with 10 ml of acetic acid/water 1:1 for 2 h, and the solid is filtered off with suction and dried under reduced pressure. This gives a solid.Yield: 1.71 g (67% of theory)LC-MS (Method 2): Rt=2.51 min.1H-NMR (400 MHz, DMSO-d6): δ=8.58 (d, 1H), 7.80 (d, 1H), 4.00 (s, 3H).
65% With sulfuric acid; nitric acid In acetic anhydride
63% With nitric acid; acetic anhydride at -40 - 15℃; for 5h; Synthesis of 4-nitro-2-(trichloroacetyl)-1-methylpyrrole Fuming nitric acid (44 mL) was added dropwise over 1 hour to a mechanically stirred solution of 2-(trichloroacetyl)-1-methyl pyrrole (118 g, 0.51 mol) in acetic anhydride (500 mL) at -40 °C (chloroform/liquid nitrogen). The temperature was kept close to -40 °C during the course of the addition. After complete addition of the nitric acid, the reaction temperature was allowed to rise to 15 °C and the reaction mixture was maintained at this temperature with the aid of an acetone/ice bath for 4 hours. It was then cooled to -30 °C and isopropanol (600 mL) was added. The mixture was stirred at -20 °C for 30 minutes and then allowed to stand for 15 min. The precipitate was collected by vacuum filtration to provide 4-nitro-2-(trichloroacetyl)-1-methylpyrrole as a white solid (87 g, 63%). TLC system: 80/20 hexane/EtOAc. 1H-NMR (CDCl3) (400 MHz) δ 7.95 (d, J = 1.76 Hz, 1H, py), 7.75 (d, J = 1.73 Hz, 1H, py), 4.05 (s, 3H, N-CH3 py). 13C-NMR (CDCl3) (400MHz) δ 173.7, 134.3, 130.1, 129.2, 121.4, 117.5, 39.7. MS m/z (ES+) (relative intensity) 272.93 (M+1).
62% With nitric acid In acetic anhydride at 20℃; for 4h;
53.3% With nitric acid In acetic anhydride at -40 - 20℃; for 2.5h;
52% With nitric acid; acetic anhydride at -40 - 20℃;
41% With nitric acid; acetic anhydride at -40℃; for 0.5h; Inert atmosphere;
With nitric acid; acetic anhydride at -40 - 20℃; Yield given;
With sulfuric acid; nitric acid In acetic anhydride
96 g With nitric acid; acetic anhydride at -5 - 10℃; for 3h;
With nitric acid In acetic anhydride at -10 - 20℃; for 4h; Inert atmosphere; General procedure for synthesis of 2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethanone 3a & 2,2,2-trichloro-1-(1-methyl-4-nitro-pyrrol-2-yl)ethanone 3b: [25-27] General procedure: The reaction was carried out using the by dissolving appropriate amounts (1equiv) of 2a or 2b in acetic anhydride. The solution was cooled to -10°C using ice-salt mixture. Calculated amount of fuming nitric acid (1.2equiv) was added to the reaction mixture dropwise, slowly over a period of 1h. The reaction was then stirred for another 2h in icebath, later removed and stirred for an hour at room temperature. The completion of reaction was monitored through TLC. The reaction mixture was poured over crushed ice and allowed to precipitate. The precipitate was filter through vacuum and the product was recrystallized using absolute alcohol or methanol.
With nitric acid; acetic anhydride at -10℃; for 2h;
With nitric acid In acetic anhydride at -10℃; for 2h; Inert atmosphere;
With nitric acid; acetic anhydride at -40 - 20℃; for 2.5h; 4 Synthesis of methyl 2,2,2-trichloro- 1 -(1 -methyl-4-nitro- 1 H-pyrrol-2-yl)ethanone 2,2,2-trichloro-1-(1-methyl-1H-pyrrol-2-yl)ethanone (35.4 g, 0.157 mol) wasdissolved in acetic anhydride (200 mL). Obtained solution was cooled down to -40 °C. Nitricacid (d = 1.5 g/mL, 1.8 eq, 14 mL) was added over period of 30 minutes. The reaction mixture was allowed to warm-up to room temperature, and stirring was continued for additional 2 hrs. The mixture was cooled down to -20 °C, then addition of isopropyl alcohol resulted in precipitation of the product which was then filtered off and washed with isopropylalcohol. ‘H-NMR (ö, CDC13, ppm) 7.91 (bs, 1H, H-5), 7.76 (bs, 1H, H-3), 4.04 (s, 3H, Me).

Reference: [1]Rahman, Khondaker M.; Reszka, Anthony P.; Gunaratnam, Mekala; Haider, Shozeb M.; Howard, Philip W.; Fox, Keith R.; Neidle, Stephen; Thurston, David E. [Chemical Communications, 2009, # 27, p. 4097 - 4099]
[2]Badaea, Concepcion; Souard, Florence; Vicent, Cristina [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10870 - 10881]
[3]Current Patent Assignee: TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES - WO2007/29364, 2007, A1 Location in patent: Page/Page column 17-18
[4]Current Patent Assignee: SHANGHAI MUSE HEALTH TECH - CN109970617, 2019, A Location in patent: Paragraph 0072; 0101-0104
[5]Alniss, Hasan Y.; Witzel, Ini-Isabeé; Semreen, Mohammad H.; Panda, Pritam Kumar; Mishra, Yogendra Kumar; Ahuja, Rajeev; Parkinson, John A. [Journal of Medicinal Chemistry, 2019]
[6]Heinrich, Benedikt; Bouazoune, Karim; Wojcik, Matthias; Bakowsky, Udo; Vázquez, Olalla [Organic and Biomolecular Chemistry, 2019, vol. 17, # 7, p. 1827 - 1833]
[7]Heinrich, Benedikt; Vázquez, Olalla [Organic Letters, 2020, vol. 22, # 2, p. 533 - 536]
[8]Current Patent Assignee: AICURIS GMBH & CO. KG - US2010/144752, 2010, A1 Location in patent: Page/Page column 8; 9
[9]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1102 - 1107]
[10]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[11]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[12]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[13]Han, Xiaochun; Li, Chun; Mosher, Michael D.; Rider, Kevin C.; Zhou, Peiwen; Crawford, Ronald L.; Fusco, William; Paszczynski, Andrzej; Natale, Nicholas R. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1671 - 1680]
[14]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[15]Baird, Eldon E.; Dervan, Peter B. [Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146]
[16]Wurtz, Nicholas R.; Turner, James M.; Baird, Eldon E.; Dervan, Peter B. [Organic Letters, 2001, vol. 3, # 8, p. 1201 - 1203]
[17]Yamamoto, Masahiko; Zhu, Changjin; Yi, Lui; Rong, Zheng; Miura, Yoshie; Izumi, Minoru; Nakajima, Shuhei; Tanamoto, Ken-Ichi; Shimizu, Sakayu; Baba, Naomichi [Bioscience, Biotechnology and Biochemistry, 2007, vol. 71, # 4, p. 1078 - 1082]
[18]Rahman, Khondaker M.; Jackson, Paul J. M.; James, Colin H.; Basu, B. Piku; Hartley, John A.; De La Fuente, Maria; Schatzlein, Andreas; Robson, Mathew; Pedley, R. Barbara; Pepper, Chris; Fox, Keith R.; Howard, Philip W.; Thurston, David E. [Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2911 - 2935]
[19]Rane, Rajesh A.; Bangalore, Pavankumar; Borhade, Sheetal D.; Khandare, Preeti K. [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 49 - 58]
[20]Rane, Rajesh A.; Naphade, Shital S.; Bangalore, Pavan Kumar; Palkar, Mahesh B.; Shaikh, Mahamadhanif S.; Karpoormath, Rajshekhar [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3079 - 3083]
[21]Rane, Rajesh A.; Naphade, Shital S.; Bangalore, Pavan Kumar; Palkar, Mahesh B.; Shaikh, Mahamadhanif S.; Karpoormath, Rajshekhar [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3079 - 3083]
[22]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2017/49091, 2017, A1 Location in patent: Paragraph 0090; 0091
  • 8
  • [ 128293-62-9 ]
  • [ 120122-47-6 ]
  • [ 142211-80-1 ]
  • 9
  • [ 4244-84-2 ]
  • [ 120122-47-6 ]
  • [ 152916-77-3 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine; In ethyl acetate; at 20℃; for 63h;Inert atmosphere; Compound 2 (30.00 g, 0.11 mol) was takenin a 500 mL round-bottom flask followed by the addition of beta-alanine ethyl ester hydrochloride (17.05 g, 0.11 mol) andEtOAc (100 mL), which had been dried over molecular sieves.TEA (35.5 mL, 0.25 mol) was dissolved in EtOAc (50 mL) anddried over sieves, and this mixture was added dropwise to thereaction mixture, while being stirred over a period of 15 hunder a nitrogen atmosphere. The reaction mixture was thenstirred for an additional 48 h during which a white precipitatewas formed. The precipitate was removed by filtration, and thefiltrate was washed with 1 M HCl (2 × 100 mL) and thendeionized (DI) water (1 × 100 mL). The organic layer wasthen dried over anhydrous magnesium sulfate and filtered, andthe solvent was removed by rotary evaporation to give 3 as ayellow solid (25.00 g, 89percent yield). Mp: 120?124 °C. TLC (1:1EtOAc/hexane): Rf = 0.42. 1H NMR (CDCl3): delta 7.47 (d, J =1.2 Hz, 1H), 6.99 (d, J = 1.6 Hz, 1H), 6.62 (s, 1H), 4.12 (q, J =7.2 Hz, 2H), 3.91 (s, 3H), 3.58 (q, J = 6 Hz, 2H), 2.54 (t, J =7.2 Hz, 2H), 1.22 (t, J = 7.2 Hz, 3H). 13C NMR: delta 171.63,160.34, 134.23, 128.32, 126.71, 107.86, 60.42, 37.78, 35.41,34.11, 14.51. IR: 3360.6, 3129.1, 1711.7, 1655.6, 1547.5,1423.7, 1355.0, 1310.1, 1197.2, 1136.4, 1111.5, 1086.4, 1020.9,986.5, 885.1, 848.4, 810.1, 821.0, 748.7, 700.1, 603.3, 595.5,583.0. HRMS (ESI): m/z for C11H15N3O5 [M + H]+ calcd270.1084, found 270.1084.
  • 10
  • [ 120122-47-6 ]
  • [ 297731-23-8 ]
  • [ 268727-20-4 ]
YieldReaction ConditionsOperation in experiment
78% In ethyl acetate
8.42 g In ethyl acetate at 20℃; for 48h; Inert atmosphere; 4.1.6. Ethyl 4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido) butanoate (5a) To 4a (8.4 g, 0.029 mol) in 50 mL of 95% EtOH in a Parr jar was added 1 g of wet 10% palladium on activated carbon. The jar was then pressurized to 70 psi with hydrogen, and shaken. When TLC (EtOAc) indicated that 4a was no longer present, the solution was filtered over Celite, which was washed with EtOH (2 × 50 mL). The combined solutions were concentrated by rotary evaporation and the remaining liquid placed under vacuum for 24 h. The resultant dark oil was dissolved in 50 mL of dry EtOAc, and 3 (8.86 g, 0.033 mol) was added. The solution was stirred under a nitrogen atmosphere for 48 h, during which time a yellow precipitate formed. The precipitate was collected by vacuum filtration to yield 5a as a bright yellow solid (8.42 g, 70% yield). Mp = 151-152 °C. TLC (EtOAc) Rf = 0.54. 1H NMR: δ 10.23 (s, 1H), 8.13 (d, J = 1.6 Hz, 1H), 8.07 (t, J = 5.6 Hz, 1H), 7.58 (d, J = 1.6 Hz, 1H), 7.20 (d, J = 1.6 Hz, 1H), 6.87 (d, J = 1.6 Hz, 1H), 4.03 (q, J = 7.2 Hz, 2H), 4.00 (s, 3H), 3.81 (s, 3H), 3.19 (q, J = 6 Hz, 2H), 2.31 (t, J = 6 Hz, 2H), 1.74 (qu, J = 6 Hz, 2H), 1.16 (t, J = 7.2 Hz, 3H). 13C NMR: δ 173.15, 161.67, 157.31, 134.27, 128.59, 126.75, 123.64, 121.83, 118.45, 108.01, 104.50, 60.20, 38.21, 37.91, 36.45, 31.51, 25.16, 14.51. HRMS (ESI) m/z for C18H23N5O6 [M+H]+ calcd 406.1721, found 406.1721.
  • 11
  • [ 120122-47-6 ]
  • [ 865-48-5 ]
  • [ 67974-08-7 ]
YieldReaction ConditionsOperation in experiment
94.6% In <i>tert</i>-butyl alcohol for 5h; Heating;
72.1% In <i>tert</i>-butyl alcohol for 2.33333h; Inert atmosphere; Reflux; Large scale; 5 Synthesis of compound d1 Adding Cl (1.5Kg, 5.5mol) and tert-butanol (12L) to a 50L reactor, stirring and dissolving under nitrogen. The alkali metal t-Bu0Na (663 g, 12.3 mol) was added in portions and stirred for 20 min. Heat to reflux for 2 h. After the reaction of the starting material was completed, the mixture was cooled to room temperature and poured into 15 L of ice water. Add 12L of ethyl acetate to extract layer, water phaseIt was extracted with 6 L of ethyl acetate. The combined organic layers were washed with EtOAc EtOAc EtOAc. Concentrate with 6L positiveBeating with hexane and 0.15 L of ethyl acetate 0.9 kg of a white solid dl were obtained in a yield 72.1%.
  • 12
  • [ 120122-47-6 ]
  • (3-{4-amino-2-[5-(3-dimethylamino-propylcarbamoyl)-1-methyl-1<i>H</i>-pyrrol-3-ylcarbamoyl]-pyrrol-1-yl}-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • [ 159539-46-5 ]
YieldReaction ConditionsOperation in experiment
81% With TEA In N,N-dimethyl-formamide at 20℃;
  • 13
  • [ 65361-30-0 ]
  • [ 120122-47-6 ]
  • [ 65361-31-1 ]
YieldReaction ConditionsOperation in experiment
22.14% Stage #1: N-[3-(dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide With hydrogen In 1,4-dioxane for 12h; Stage #2: 1-methyl-4-nitro-2-trichloroacetylpyrrole In N,N-dimethyl-formamide at 0 - 20℃;
  • 14
  • [ 120122-47-6 ]
  • [ 65361-31-1 ]
  • [ 65361-32-2 ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: N-[3-(dimethylamino)propyl]-1-methyl-4-[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxamide With hydrogen In 1,4-dioxane for 12h; Stage #2: 1-methyl-4-nitro-2-trichloroacetylpyrrole In N,N-dimethyl-formamide at 0 - 20℃;
  • 15
  • [ 593-51-1 ]
  • [ 120122-47-6 ]
  • [ 67973-90-4 ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;
  • 16
  • [ 120122-47-6 ]
  • [ 373362-34-6 ]
  • [ 163012-91-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 29℃;
3.5 g In N,N-dimethyl-formamide at 0 - 20℃;
In N,N-dimethyl-formamide at 0 - 20℃; for 10h; 6 The compound 14 (3.6 g, 9. 6 mmol) was dissolved in methanol (38 mL), mixed with 10 % Pd/C (481 mg) and stirred under hydrogen atmosphere for four hours at a room temperature. 10% Pd/C was filtered out, and the solvent was distilled out. The residue was dissolved in DMF (10 mL), followed by azeotropy to reduce its volume by half so as to remove methanol. The compound 11 (2.6 g, 9.6 mmol) dissolved in DMF (10 ml) was added to the resulting solution at 0 °C. After being heated to a room temperature, the solvent was distilled out and the residue was washed with 2-propanol to give the compound 15 (3.5 g, 74 %). 1HNMR (DMSO-d6) δ 1.74-1.77(2H, t, J=6.1Hz), 2.27(6H, s), 2.43-2.46(2H, t, J=6.1Hz), 3.49-3.53(2H, m), 3.86(3H, s), 4.05(6H, s), 6.57(1H, s),7.16(1H, s), 7.27(1H, s),7.44(1H, s), 7.61(1H, s), 7.69(1H, s), 7.90(1H, m), 8.58(1H, s), 9.25(1H, s).
  • 18
  • [ 23159-07-1 ]
  • [ 120122-47-6 ]
  • [ 566946-97-2 ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran at 20℃;
  • 19
  • [ 6937-16-2 ]
  • [ 120122-47-6 ]
  • [ 268727-19-1 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In ethyl acetate; at 20℃;Inert atmosphere; Compound 3 (10.1 g, 0.037 mol) was placed in a 500 mL round bottom flask and dissolved in 75 mL of dry EtOAc. Ethyl 4-amino-butyrate hydrochloride (9.35 g, 0.058 mol) was added to the flask. Dry TEA (15.05 mL, 0.108 mol) was added to the flask dropwise over 1 h. The reaction mixture was stirred under a nitrogen atmosphere. When TLC (EtOAc) indicated that 3 was absent, the solution was filtered by vacuum filtration to remove the white solid precipitate that was present. The filtrate was transferred to a 500 mL separatory funnel, and the organic layer was washed with 1 M HCl (2 × 100 mL), DI H2O (1 × 100 mL), 5% NaHCO3 (2 × 100 mL), and DI H2O (1 × 100 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. The residue was placed under vacuum for 24 h to yield 4a as a yellow solid (8.44 g, 80% yield). Mp = 63-65 C. TLC (1:1 EtOAc/hexane) Rf = 0.25; 1H NMR (CDCl3) delta 7.54 (d, J = 1.6 Hz, 1H), 7.08 (d, J = 1.6 Hz, 1H), 6.54-6.50 (br s, 1H), 4.16 (q, J = 7.2 Hz, 2H), 3.99 (s, 3H), 3.44 (q, J = 7.2 Hz, 2H), 2.44 (t, J = 6.8 Hz, 2H), 1.94 (qu, J = 6.8 Hz, 2H), 1.26 (t, J = 7.2 Hz, 3H). 13C NMR (CDCl3) delta 173.72, 160.54, 134.78, 126.72, 126.49, 107.08, 60.72, 39.13, 37.84, 31.90, 24.35, 14.13. HRMS (ESI) m/z for C12H17N3O5 [M+H]+ calcd 284.1241, found 284.1240.
  • 20
  • [ 120122-47-6 ]
  • [ 297731-23-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / triethylamine / tetrahydrofuran / 24 h / Heating 2: H2 / Pd/C / methanol / 24 h / 20 °C / atm. press.
Multi-step reaction with 2 steps 1: 99 percent / triethylamine / ethyl acetate / 1 h / 20 °C 2: H2 / Pd/C / methanol / 5 h / 20 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr
Multi-step reaction with 2 steps 1: 75 percent / ethyl acetate 2: H2
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 18 h / Reflux 2: 5% Pd(II)/C(eggshell); hydrogen / ethanol / 20 °C
Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3620.13 Torr
Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate / 4 h / 20 °C 2: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C

  • 21
  • [ 96-54-8 ]
  • [ 120122-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / 4.5 h 2: 62 percent / nitric acid / acetic anhydride / 4 h / 20 °C
Multi-step reaction with 2 steps 1: 41 percent / CH2Cl2 2: 53.3 percent / 70 percent HNO3 / acetic anhydride / 2.5 h / -40 - 20 °C
Multi-step reaction with 2 steps 1: 1.2 kg / diethyl ether / 3 h 2: HNO3, Ac2O / -40 - 20 °C
Multi-step reaction with 2 steps 1: 100 percent / CH2Cl2 / 3 h 2: 69 percent / HNO3 / acetic anhydride / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: diethyl ether 2: HNO3; acetic anhydride / isopropanol / -40 °C
Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 20 °C / Inert atmosphere 2: acetic anhydride; HNO3 / 3 h / -5 - 10 °C
Multi-step reaction with 2 steps 1: dichloromethane / 3 h / 20 °C / Inert atmosphere 2: acetic anhydride; HNO3 / 0.5 h / -40 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / diethyl ether / Inert atmosphere 2: HNO3 / acetic anhydride / 4 h / -10 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / diethyl ether 2: HNO3; acetic anhydride / 2 h / -10 °C
Multi-step reaction with 2 steps 1: potassium carbonate / diethyl ether / Inert atmosphere 2: HNO3 / acetic anhydride / 2 h / -10 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: diethyl ether / 6 h 2: HNO3; acetic anhydride / 5 h / -40 - 15 °C
Multi-step reaction with 2 steps 1: dichloromethane / 24 h / 20 °C 2: acetic anhydride; HNO3 / 2.5 h / -40 - 20 °C
Multi-step reaction with 2 steps 1: diethyl ether / 0 - 20 °C / Inert atmosphere 2: acetic anhydride; HNO3 / -40 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dichloromethane / -5 - 20 °C / Inert atmosphere; Large scale 2: HNO3; acetic anhydride / 0.5 h / -40 - 20 °C / Inert atmosphere; Large scale
Multi-step reaction with 2 steps 1: dichloromethane / 20 h / 20 °C / Inert atmosphere 2: acetic anhydride; HNO3 / 0.5 h / -25 - 0 °C
Multi-step reaction with 2 steps 1: diethyl ether / 17 h / 0 - 20 °C / Inert atmosphere 2: acetic anhydride; HNO3 / 16.5 h / -40 - 20 °C
Multi-step reaction with 2 steps 1: diethyl ether / 1.5 h / 20 °C 2: HNO3; acetic anhydride / 3 h / -5 - 20 °C

Reference: [1]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[2]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[3]Baird, Eldon E.; Dervan, Peter B. [Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146]
[4]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[5]Badaea, Concepcion; Souard, Florence; Vicent, Cristina [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10870 - 10881]
[6]Rahman, Khondaker M.; Jackson, Paul J. M.; James, Colin H.; Basu, B. Piku; Hartley, John A.; De La Fuente, Maria; Schatzlein, Andreas; Robson, Mathew; Pedley, R. Barbara; Pepper, Chris; Fox, Keith R.; Howard, Philip W.; Thurston, David E. [Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2911 - 2935]
[7]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[8]Rane, Rajesh A.; Bangalore, Pavankumar; Borhade, Sheetal D.; Khandare, Preeti K. [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 49 - 58]
[9]Rane, Rajesh A.; Naphade, Shital S.; Bangalore, Pavan Kumar; Palkar, Mahesh B.; Shaikh, Mahamadhanif S.; Karpoormath, Rajshekhar [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3079 - 3083]
[10]Rane, Rajesh A.; Naphade, Shital S.; Bangalore, Pavan Kumar; Palkar, Mahesh B.; Shaikh, Mahamadhanif S.; Karpoormath, Rajshekhar [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3079 - 3083]
[11]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[12]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2017/49091, 2017, A1
[13]Heinrich, Benedikt; Bouazoune, Karim; Wojcik, Matthias; Bakowsky, Udo; Vázquez, Olalla [Organic and Biomolecular Chemistry, 2019, vol. 17, # 7, p. 1827 - 1833]
[14]Current Patent Assignee: SHANGHAI MUSE HEALTH TECH - CN109970617, 2019, A
[15]Alniss, Hasan Y.; Witzel, Ini-Isabeé; Semreen, Mohammad H.; Panda, Pritam Kumar; Mishra, Yogendra Kumar; Ahuja, Rajeev; Parkinson, John A. [Journal of Medicinal Chemistry, 2019]
[16]Heinrich, Benedikt; Vázquez, Olalla [Organic Letters, 2020, vol. 22, # 2, p. 533 - 536]
[17]Current Patent Assignee: PEKING UNIVERSITY - WO2022/105825, 2022, A1
  • 22
  • [ 120122-47-6 ]
  • [ 78486-16-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.25 g / dimethylformamide / 0 - 20 °C 2: H2 / PtO2 / methanol / 20 °C
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 1 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C 3: 1.25 g / dimethylformamide / 0 - 20 °C 4: H2 / PtO2 / methanol / 20 °C
Multi-step reaction with 4 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: i-Pr2NEt / CH2Cl2 / 20 °C 4: H2 / 10 percent Pd/C / methanol / 20 °C
Multi-step reaction with 3 steps 1.1: 66 percent / CH2Cl2 / 1 h / 0 - 20 °C 2.1: H2 / Pd/C / dioxane / 12 h 2.2: 22.14 percent / dimethylformamide / 0 - 20 °C 3.1: H2 / Pd on charcoal / methanol
Multi-step reaction with 2 steps 1.1: H2 / Pd/C / dioxane / 12 h 1.2: 22.14 percent / dimethylformamide / 0 - 20 °C 2.1: H2 / Pd on charcoal / methanol
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 2 h / 20 °C 2: H2 / Pd/C / dimethylformamide; methanol 3: dimethylformamide / 18 h / 20 °C 4: H2 / Pd/C / dimethylformamide; methanol
Multi-step reaction with 2 steps 1: 87 percent / dimethylformamide / from 0 degC to room t. 2: H2 / PtO2 / methanol / 3 h
Multi-step reaction with 4 steps 1: 99 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: H2 / PtO2 / methanol / 3 h 3: 87 percent / dimethylformamide / from 0 degC to room t. 4: H2 / PtO2 / methanol / 3 h
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: tetrahydrofuran / 0.03 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / Inert atmosphere 3: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dichloromethane / 1 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 10 h / 2068.65 Torr
Multi-step reaction with 4 steps 1: tetrahydrofuran / 2 h 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 3.5 h / 2068.65 Torr 3: dichloromethane / 1 h / 20 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 10 h / 2068.65 Torr
Multi-step reaction with 4 steps 2: hydrogen / palladium on activated charcoal 4: hydrogen / palladium on activated charcoal

Reference: [1]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[2]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[3]Bando, Toshikazu; Narita, Akihiko; Saito, Isao; Sugiyama, Hiroshi [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3471 - 3485]
[4]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[5]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[6]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [European Journal of Organic Chemistry, 2000, # 11, p. 2095 - 2103]
[7]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[8]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[9]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[10]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[11]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[12]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[13]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2005/32594, 2005, A2
  • 23
  • [ 120122-47-6 ]
  • [ 78486-14-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / tetrahydrofuran / 1 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 84 percent / tetrahydrofuran / 0 - 20 °C 2: H2 / Pd/C / ethanol / 4 h / 20 °C
Multi-step reaction with 2 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 66 percent / CH2Cl2 / 1 h / 0 - 20 °C 2: H2 / Pd on charcoal / methanol
Multi-step reaction with 2 steps 1: 96 percent / tetrahydrofuran / 2 h / 20 °C 2: H2 / Pd/C / dimethylformamide; methanol
Multi-step reaction with 2 steps 1: 99 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: H2 / PtO2 / methanol / 3 h
Multi-step reaction with 2 steps 1: dichloromethane / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2327.23 Torr
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.03 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 3.5 h / 2068.65 Torr
Multi-step reaction with 2 steps 2: hydrogen / palladium on activated charcoal
Multi-step reaction with 4 steps 1.1: dmap / 72 h / 20 °C 2.1: sodium hydroxide; methanol / water / 60 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / 0 - 20 °C 3.2: 16 h / 0 - 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h

Reference: [1]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[2]Seio, Kohji; Mizuta, Masahiro; Terada, Takeshi; Sekine, Mitsuo [Journal of Organic Chemistry, 2005, vol. 70, # 25, p. 10311 - 10322]
[3]Bando, Toshikazu; Narita, Akihiko; Saito, Isao; Sugiyama, Hiroshi [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3471 - 3485]
[4]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[5]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [European Journal of Organic Chemistry, 2000, # 11, p. 2095 - 2103]
[6]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[7]Ong, Chi Wi; Yang, Ya-Ting; Liu, Meng-Chi; Fox, Keith R.; Liu, Ping Hao; Tung, Hung-Wei [Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1040 - 1046]
[8]Rahman, Khondaker M.; Jackson, Paul J. M.; James, Colin H.; Basu, B. Piku; Hartley, John A.; De La Fuente, Maria; Schatzlein, Andreas; Robson, Mathew; Pedley, R. Barbara; Pepper, Chris; Fox, Keith R.; Howard, Philip W.; Thurston, David E. [Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2911 - 2935]
[9]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[10]Brucoli, Federico; Guzman, Juan D.; Maitra, Arundhati; James, Colin H.; Fox, Keith R.; Bhakta, Sanjib [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3705 - 3711]
[11]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2005/32594, 2005, A2
[12]Heinrich, Benedikt; Bouazoune, Karim; Wojcik, Matthias; Bakowsky, Udo; Vázquez, Olalla [Organic and Biomolecular Chemistry, 2019, vol. 17, # 7, p. 1827 - 1833]
  • 24
  • [ 120122-47-6 ]
  • [ 65361-32-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.25 g / dimethylformamide / 0 - 20 °C 2: H2 / PtO2 / methanol / 20 °C 3: 407 mg / dimethylformamide / 0 - 20 °C
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 1 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C 3: 1.25 g / dimethylformamide / 0 - 20 °C 4: H2 / PtO2 / methanol / 20 °C 5: 407 mg / dimethylformamide / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: 66 percent / CH2Cl2 / 1 h / 0 - 20 °C 2.1: H2 / Pd/C / dioxane / 12 h 2.2: 22.14 percent / dimethylformamide / 0 - 20 °C 3.1: H2 / Pd/C / dioxane / 12 h 3.2: 34 percent / dimethylformamide / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: H2 / Pd/C / dioxane / 12 h 1.2: 22.14 percent / dimethylformamide / 0 - 20 °C 2.1: H2 / Pd/C / dioxane / 12 h 2.2: 34 percent / dimethylformamide / 0 - 20 °C
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 2 h / 20 °C 2: H2 / Pd/C / dimethylformamide; methanol 3: dimethylformamide / 18 h / 20 °C 4: H2 / Pd/C / dimethylformamide; methanol 5: dimethylformamide; tetrahydrofuran / 20 °C
Multi-step reaction with 3 steps 1: 87 percent / dimethylformamide / from 0 degC to room t. 2: H2 / PtO2 / methanol / 3 h 3: 79 percent / dimethylformamide
Multi-step reaction with 5 steps 1: 99 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: H2 / PtO2 / methanol / 3 h 3: 87 percent / dimethylformamide / from 0 degC to room t. 4: H2 / PtO2 / methanol / 3 h 5: 79 percent / dimethylformamide
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: tetrahydrofuran / 0.03 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / Inert atmosphere 3: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere 5: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere

Reference: [1]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[2]Wender; Jeon [Organic letters, 1999, vol. 1, # 13, p. 2117 - 2120]
[3]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[4]Hotzel, Christian; Marotto, Annalisa; Pindur, Ulf [European Journal of Medicinal Chemistry, 2003, vol. 38, # 2, p. 189 - 197]
[5]Sharma, Sanjay K.; Tandon, Manju; Lown, J. William [European Journal of Organic Chemistry, 2000, # 11, p. 2095 - 2103]
[6]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[7]Nishiwaki, Eiji; Tanaka, Shigeaki; Lee, Hideaki; Shibuya, Masayuki [Heterocycles, 1988, vol. 27, # 8, p. 1945 - 1952]
[8]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
[9]LaPensee, Louise; Sabbani, Sunil; Sharma, Raman; Bhamra, Inder; Shore, Emma; Chadwick, Amy E.; Berry, Neil G.; Firman, James; Araujo, Nuna C.; Cabral, Lilia; Cristiano, Maria L. S.; Bateman, Cerys; Janneh, Omar; Gavrila, Adelina; Wu, Yi Hang; Hussain, Afthab; Ward, Stephen A.; Stocks, Paul A.; Cosstick, Rick; O'Neill, Paul M. [ChemMedChem, 2013, vol. 8, # 5, p. 709 - 718]
  • 25
  • [ 120122-47-6 ]
  • [ 65361-31-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 1 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C 3: 1.25 g / dimethylformamide / 0 - 20 °C
Multi-step reaction with 3 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: i-Pr2NEt / CH2Cl2 / 20 °C
Multi-step reaction with 2 steps 1.1: 66 percent / CH2Cl2 / 1 h / 0 - 20 °C 2.1: H2 / Pd/C / dioxane / 12 h 2.2: 22.14 percent / dimethylformamide / 0 - 20 °C
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 2 h / 20 °C 2: H2 / Pd/C / dimethylformamide; methanol 3: dimethylformamide / 18 h / 20 °C
Multi-step reaction with 3 steps 1: 99 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: H2 / PtO2 / methanol / 3 h 3: 87 percent / dimethylformamide / from 0 degC to room t.
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.03 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / Inert atmosphere 3: N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: tetrahydrofuran / 2 h 2: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 3.5 h / 2068.65 Torr 3: dichloromethane / 1 h / 20 °C
Multi-step reaction with 3 steps 2: hydrogen / palladium on activated charcoal

  • 26
  • [ 120122-47-6 ]
  • 4-({4-[(4-amino-1-methyl-1<i>H</i>-pyrrole-2-carbonyl)-amino]-1-methyl-1<i>H</i>-pyrrole-2-carbonyl}-amino)-butyric acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 99 percent / triethylamine / ethyl acetate / 1 h / 20 °C 2: H2 / Pd/C / methanol / 5 h / 20 °C / 760.05 Torr 3: 6.28 g / 3-(diethoxy-phosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / tetrahydrofuran / 24 h 4: trifluoroacetic acid / CH2Cl2; H2O / 1 h
Multi-step reaction with 4 steps 1: 75 percent / ethyl acetate 2: H2 3: 78 percent / ethyl acetate 4: H2 / Pd/C / dimethylformamide
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 18 h / Reflux 2: 5% Pd(II)/C(eggshell); hydrogen / ethanol / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C 4: 5% Pd(II)/C(eggshell); hydrogen / ethanol / 20 °C
Multi-step reaction with 4 steps 1: triethylamine / ethyl acetate / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3620.13 Torr 3: ethyl acetate / 48 h / 20 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3620.13 Torr
Multi-step reaction with 2 steps 1: ethyl acetate / 48 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3620.13 Torr

  • 27
  • [ 120122-47-6 ]
  • [ 152916-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: TEA / ethyl acetate / ultrasonic irradiation 1.2: 93 percent / ethyl acetate / 5 h / 20 °C 2.1: H2 / Pd/C / ethanol / 6 h / 20 °C
Multi-step reaction with 2 steps 1: EtOAc 2: H2 / Pd/C / ethyl acetate
Multi-step reaction with 2 steps 1.1: Et3N / ethyl acetate 1.2: 78 percent / ethyl acetate 2.1: H2 / Pd/C / ethyl acetate
Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate / 1 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 3620.13 Torr

  • 28
  • [ 120122-47-6 ]
  • [ 910545-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: TEA / ethyl acetate / ultrasonic irradiation 1.2: 93 percent / ethyl acetate / 5 h / 20 °C 2.1: H2 / Pd/C / ethanol / 6 h / 20 °C 3.1: HOBt; DCC / CHCl3; dimethylformamide / 8 h / 20 °C 3.2: CHCl3; dimethylformamide / 24 h / 20 °C 4.1: H2 / Pd/C / dimethylformamide / 6 h / 20 °C
Multi-step reaction with 2 steps 1: NaH / tetrahydrofuran 2: H2 / Pd/C / dimethylformamide / 9 h / 20 °C
Multi-step reaction with 4 steps 1: EtOAc 2: H2 / Pd/C / ethyl acetate 3: NaH / tetrahydrofuran 4: H2 / Pd/C / dimethylformamide / 9 h / 20 °C
Multi-step reaction with 4 steps 1.1: Et3N / ethyl acetate 1.2: 78 percent / ethyl acetate 2.1: H2 / Pd/C / ethyl acetate 3.1: 78 percent / ethyl acetate 4.1: H2 / Pd/C / dimethylformamide
Multi-step reaction with 4 steps 1: triethylamine / ethyl acetate / 1 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 3620.13 Torr 3: ethyl acetate / 48 h / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / ethanol / 3878.71 Torr

  • 29
  • [ 120122-47-6 ]
  • [ 152916-79-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: TEA / ethyl acetate / ultrasonic irradiation 1.2: 93 percent / ethyl acetate / 5 h / 20 °C 2.1: H2 / Pd/C / ethanol / 6 h / 20 °C 3.1: HOBt; DCC / CHCl3; dimethylformamide / 8 h / 20 °C 3.2: CHCl3; dimethylformamide / 24 h / 20 °C
Multi-step reaction with 3 steps 1: EtOAc 2: H2 / Pd/C / ethyl acetate 3: NaH / tetrahydrofuran
Multi-step reaction with 3 steps 1.1: Et3N / ethyl acetate 1.2: 78 percent / ethyl acetate 2.1: H2 / Pd/C / ethyl acetate 3.1: 78 percent / ethyl acetate
Multi-step reaction with 3 steps 1: triethylamine / ethyl acetate / 1 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 3620.13 Torr 3: ethyl acetate / 48 h / Inert atmosphere

  • 30
  • [ 120122-47-6 ]
  • [ 861668-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C 4: 7.52 g / aq. NaOH / methanol / 0.02 h
Multi-step reaction with 4 steps 1.1: triethylamine / ethyl acetate / 4 h / 20 °C 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C 3.1: dmap / 7 h 3.2: DIPC / 24 h 4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h
  • 31
  • [ 120122-47-6 ]
  • [ 861668-81-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C
Multi-step reaction with 3 steps 1.1: triethylamine / ethyl acetate / 4 h / 20 °C 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C 3.1: dmap / 7 h 3.2: DIPC / 24 h
  • 32
  • [ 120122-47-6 ]
  • 1<i>H</i>-indole-2-carboxylic acid [1-methyl-5-(3-methylcarbamoyl-propylcarbamoyl)-1<i>H</i>-pyrrol-3-yl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2.1: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3.1: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C 4.1: 7.52 g / aq. NaOH / methanol / 0.02 h 5.1: HOBt; DIPC; Et3N / dimethylformamide / 24 h / 20 °C 5.2: 140 mg / Et3N / dimethylformamide / 24 h / 20 °C
  • 33
  • [ 120122-47-6 ]
  • β-D-Glc-N-methyl-pyrrolcarboxamide-γ-aminobutyric acid-N-methyl-pyrrolcarboxamide-Ind [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2.1: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3.1: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C 4.1: 7.52 g / aq. NaOH / methanol / 0.02 h 5.1: DIPC; HOBt / dimethylformamide / 24 h / 20 °C 5.2: 450 mg / dimethylformamide / 24 h / 20 °C 6.1: NaOMe / methanol / 0.02 h
Multi-step reaction with 7 steps 1.1: 0.5 h 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / methanol; ethyl acetate; water / 0 °C 3.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h 3.2: 24 h 4.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 168 h 5.1: N,N,N',N'-tetramethylformamidium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 7.1: sodium methylate; methanol
Multi-step reaction with 9 steps 1.1: triethylamine / ethyl acetate / 4 h / 20 °C 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C 3.1: dmap / 7 h 3.2: DIPC / 24 h 4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h 5.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h 5.2: 24 h 6.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 168 h 7.1: N,N,N',N'-tetramethylformamidium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 9.1: sodium methylate; methanol
  • 34
  • [ 120122-47-6 ]
  • β-D-Gal-N-methyl-pyrrolcarboxamide-γ-aminobutyric acid-N-methyl-pyrrolcarboxamide-Ind [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2.1: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3.1: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C 4.1: 7.52 g / aq. NaOH / methanol / 0.02 h 5.1: DIPC; HOBt / dimethylformamide / 24 h / 20 °C 5.2: 140 mg / dimethylformamide / 24 h / 20 °C 6.1: NaOMe / methanol / 0.02 h
Multi-step reaction with 7 steps 1.1: 0.5 h 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / methanol; ethyl acetate; water / 0 °C 3.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h 3.2: 24 h 4.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 168 h 5.1: N,N,N',N'-tetramethylformamidium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 7.1: sodium methylate; methanol
Multi-step reaction with 9 steps 1.1: triethylamine / ethyl acetate / 4 h / 20 °C 2.1: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C 3.1: dmap / 7 h 3.2: DIPC / 24 h 4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h 5.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h 5.2: 24 h 6.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 168 h 7.1: N,N,N',N'-tetramethylformamidium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 9.1: sodium methylate; methanol
  • 35
  • [ 120122-47-6 ]
  • acetic acid 4,5-diacetoxy-2-({4-[4-({4-[(1<i>H</i>-indole-2-carbonyl)-amino]-1-methyl-1<i>H</i>-pyrrole-2-carbonyl}-amino)-butyrylamino]-1-methyl-1<i>H</i>-pyrrole-2-carbonyl}-amino)-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 90 percent / Et3N / ethyl acetate / 24 h / 20 °C 2.1: H2 / Pd/C / ethyl acetate / 24 h / 2327.17 Torr 3.1: 190 mg / HOBt; DIPC; DMAP / CH2Cl2 / 20 °C 4.1: 7.52 g / aq. NaOH / methanol / 0.02 h 5.1: DIPC; HOBt / dimethylformamide / 24 h / 20 °C 5.2: dimethylformamide / 24 h / 20 °C
  • 36
  • [ 120122-47-6 ]
  • [ 128484-11-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 84 percent / tetrahydrofuran / 0 - 20 °C 2: H2 / Pd/C / ethanol / 4 h / 20 °C 3: 3.68 g / dimethylformamide / 0 - 20 °C
Multi-step reaction with 3 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: 587 mg / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C
  • 37
  • [ 120122-47-6 ]
  • [ 373362-34-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 84 percent / tetrahydrofuran / 0 - 20 °C 2: H2 / Pd/C / ethanol / 4 h / 20 °C 3: 3.68 g / dimethylformamide / 0 - 20 °C 4: H2 / Pd/C / methanol / 4 h / 20 °C
Multi-step reaction with 4 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: 587 mg / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C 4: H2 / 10 percent Pd/C / methanol / 4 h / 20 °C
  • 38
  • [ 120122-47-6 ]
  • [ 773897-01-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 84 percent / tetrahydrofuran / 0 - 20 °C 2: H2 / Pd/C / ethanol / 4 h / 20 °C 3: 3.68 g / dimethylformamide / 0 - 20 °C 4: H2 / Pd/C / methanol / 4 h / 20 °C 5: 3.5 g / dimethylformamide / 0 - 20 °C 6: H2 / Pd/C / methanol / 4 h / 20 °C
Multi-step reaction with 6 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: 587 mg / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C 4: H2 / 10 percent Pd/C / methanol / 4 h / 20 °C 5: i-Pr2NEt / CH2Cl2 / 29 °C 6: NaBH4; Pd/C / methanol; ethyl acetate; H2O / 20 °C
  • 39
  • [ 120122-47-6 ]
  • [ 163012-91-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 84 percent / tetrahydrofuran / 0 - 20 °C 2: H2 / Pd/C / ethanol / 4 h / 20 °C 3: 3.68 g / dimethylformamide / 0 - 20 °C 4: H2 / Pd/C / methanol / 4 h / 20 °C 5: 3.5 g / dimethylformamide / 0 - 20 °C
Multi-step reaction with 5 steps 1: 97 percent / 12 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 2 h / 20 °C 3: 587 mg / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C 4: H2 / 10 percent Pd/C / methanol / 4 h / 20 °C 5: i-Pr2NEt / CH2Cl2 / 29 °C
  • 40
  • [ 120122-47-6 ]
  • [ 13138-78-8 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 4-Nitro-2-trichloroacetyl-1-methylpyrrole With sodium hydroxide In lithium hydroxide monohydrate at 20℃; for 5h; Stage #2: With hydrogenchloride In lithium hydroxide monohydrate 2 Synthesis of 2-(4-tert-butoxycarbonylamino-1-methyl-1H-pyrrol-2-yl)-1-methyl-1H-benzoimidazole-5-carboxylic acid; 4-nitro-1-methylpyrrole-2-carboxylic acid 4-nitro-1-methylpyrrolE-2-carboxylic acid : A solution of NAOH (5.64 g, 140.9 MMOL) in water (250 mL) was added 4-nitro-2-(trichloroacetyl)-1-methylpyrrole (12.75 g, 47.0 MMOL) at room temperature. The mixture was stirred for 5 hours at room temperature, then was extracted with ethyl acetate (80 mL). The aqueous layer was acidified with 2N HCI to pH=3, and the resulting solid was filtered and dried in vacuo to afford 7.71 g (97%) of product as a white SOLID.1H NMR (300 MHz, CDCI3) 5 7.65 (d, J=2.1 Hz, 1 H), 7.55 (d, J=2.1 Hz, 1 H), 4.01 (s, 3 H). Anal. CALCD FOR C6H6N204 : C, 42.36 ; H, 3.55 ; N, 16.47. Found: C, 42.53 ; H, 3.60 ; N, 16.49.
88% Stage #1: 4-Nitro-2-trichloroacetyl-1-methylpyrrole With sodium hydroxide In ethanol; lithium hydroxide monohydrate Reflux; Inert atmosphere; Stage #2: With hydrogenchloride; lithium hydroxide monohydrate In ethanol at 20℃;
82% With sodium hydroxide In lithium hydroxide monohydrate at 20℃; for 12h;
Multi-step reaction with 2 steps 1: 100 percent / 80 °C 2: NaOH / tetrahydrofuran; methanol / 20 °C
With lithium hydroxide monohydrate; potassium hydroxide In methanol
With lithium hydroxide monohydrate; sodium hydroxide In ethanol Reflux; Inert atmosphere;
Multi-step reaction with 2 steps 1.1: sodium hydride / 2 h / 20 °C 2.1: sodium hydroxide / 17 h / 20 °C 2.2: 0.25 h / 20 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-4-aminopyridine / 72 h / 20 °C 2: sodium hydroxide; methanol / lithium hydroxide monohydrate / 60 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-4-aminopyridine / 72 h / 20 °C 2: sodium hydroxide; lithium hydroxide monohydrate / methanol / 17 h / 20 - 60 °C

  • 41
  • [ 120122-47-6 ]
  • [ 72083-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / 80 °C 2: H2 / Pd/C / methanol / 2 h / 2585.81 Torr
Multi-step reaction with 2 steps 1: 96 percent / NaH / 1 h / 20 °C 2: H2 / 10 percent Pd/C / methanol / 20 °C
Multi-step reaction with 2 steps 1: 47 percent / NaOMe / 2 h / Ambient temperature 2: H2 / 10percent Pd/C / ethyl acetate / 48 h / 836 Torr
Multi-step reaction with 2 steps 1: 0.5 h 2: sodium tetrahydroborate; 5%-palladium/activated carbon / methanol; ethyl acetate; water / 0 °C
Multi-step reaction with 2 steps 1: dmap / 72 h / 20 °C 2: hydrogen; 5%-palladium/activated carbon / tetrahydrofuran / 2 h

  • 42
  • [ 120122-47-6 ]
  • [ 13138-76-6 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 1-methyl-4-nitro-2-trichloroacetylpyrrole With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: With sulfuric acid In methanol Heating / reflux; 4 Synthesis of 1-methyl-1H-pyrrolO[3,2-b]pyridine-2-carboxylic acid; methyl 1-methyl-4-nitropyrrole-2-carboxylate To a solution of 4-nitro-2-(trichloroacetyl)-1-methylpyrrole (48.6 g, 179.0 MMOL) in methanol (130 mL) was added NaOCH3 (100 MG, 1.85 MMOL) at room temperature. After exotherm ceased in 30 min, 98% H2SO4 (0.85 mL) and methanol (200 mL) were added.The mixture was heated to reflux until all the solid dissolved, then cooled to room temperature. The solid was collected by filtration and dried in vacuo to afford 30.34 g (92%) as a white SOLID. 1H NMR (300 MHz, CDCI3) # 7.60 (d, J=1.8 Hz, 1 H), 7.41 (d, J=1.8 Hz, 1H), 3.99 (s, 3H), 3.86 (s, 3H).
  • 43
  • [ 120122-47-6 ]
  • [ 109-76-2 ]
  • [ 358976-66-6 ]
YieldReaction ConditionsOperation in experiment
92% In tetrahydrofuran for 3h; 7.a Example 7; Synthesis of dimer 15 (AT-281); a) Preparation of 24; 1-methyl-2-trichloroacetyl-4-nitropyrrole (23) (2 g, 7.36 mmol, J. Am. Chem. Soc., 118, 1996, 6141-46) and 1,3-diaminopropane (307 pL, 3.67 mmol) were dissolved in anhydrous THF (15 mL). The formation of a precipitate was observed after 5 min and the suspension was allowed to stir for 3 h. Following dilution with diethyl ether (60 mL), the precipitate was collected by filtration and dried in vacuo to yield 24 as an off-white fine powder (1.28 g, 92%) : 1H NMR (400 MHz, DMSO-d6) 5 8.40 (t, J = 5.4 Hz, 2H), 8.12 (d, J = 1.51 Hz, 2H), 7.42 (d, J = 1.88 Hz, 2H), 3.92 (s, 6H), 3. 26 (q, J = 6. 49 Hz, 4H), 1. 75 (p, J = 6.88 Hz, 2H) ; 13C NMR (100 MHz, DMSO-d6) 5 159.8, 133.7, 127. 7, 126. 4, 107.2, 37. 3, 36. 5, 28.8 ; MS (ES+) m/z (relative intensity) 379 ([M + H] +-, 100); IR (CHC13) 3414,3364, 3116, 2950,1654, 550, 1530,1501, 1418,1346, 1311, 1264,1222, 1209,1139, 1111,1075, 984,950, 827,849, 811, 747, 707 cm 1.
86% In tetrahydrofuran at 5 - 20℃;
  • 44
  • [ 96-54-8 ]
  • [ 35302-72-8 ]
  • [ 76-02-8 ]
  • [ 120122-47-6 ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate In diethyl ether; water; acetic anhydride 1 Preparation of Methyl 1-methyl-4-nitropyrrole-2-carboxylate (6) and Ethyl 1-methyl-4-nitroimidazole-2-carboxylate (10) STR18 Preparation of 4-nitro-2-trichloroacetyl-1-methylpyrrole (15) To a well stirred solution of trichloroacetylchloride (1 kg, 5.5 mole) in 1.5 liters of ethyl ether was added dropwise over a period of 3 hours a solution of N-methylpyrrole (14) (0.45 kg, 5.5 mole) in 1.5 liters of anhydrous ethyl ether. The reaction was allowed to stir for an additional 3 hours and quenched by the dropwise addition of a solution of 400 g of potassium carbonate in 1.5 liters of water. The layers were separated and the ether layer was concentrated in vacuo to provide 2-trichloroacetyl pyrrole (1.2 kg, 5.1 mole) as a yellow crystalline solid, which can be purified by recrystallization from benzene, but is sufficiently pure to be used without further purification. To a cooled (-40° C.) solution of 2-trichloroacetyl pyrrole (1.2 kg, 5.1 mole) in acetic anhydride (6 liters) flask equipped with a mechanical stirrer was added 440 ml of fuming nitric acid over a period of 1 hour while maintaining a temperature of -40° C. The reaction was carefully allowed to warm to room temperature and stirred an additional 4 hours after which the mixture was cooled to -30° C. and isopropyl alcohol (6 liters) was added. The solution was stirred at -20° C. for 30 minutes during which time a white precipitate formed. The solution was allowed to stand for 15 minutes and the resulting precipitate collected by vacuum filtration to provide (15) (0.8 kg, 54% yield). TLC (7:2 benzene/ethyl acetate) Rf 0.7; 1 H NMR (DMSO-d6) δ 8.55 (d, 1 H, J=1.7 Hz), 7.77 (d, 1 H, J=1.7 Hz), 3.98 (s, 3 H); 13 C NMR (DMSO-d6) δ 173.3, 134.7, 133.2, 121.1, 116.9, 95.0, 51.5; IR (KBr) 1694, 1516, 1423, 1314, 1183, 1113, 998, 750; FABMS m/e 269.936 (M+H 269.937 calc. for C7 H5 N2 O3 Cl3).
  • 45
  • [ 126824-12-2 ]
  • [ 120122-47-6 ]
  • [ 934992-84-4 ]
  • [ 934992-85-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 16h; Diamine 6 (3.1 g, 15 mmol) was dissolved in CH3CN (60 mL) and the solution added to a stirred mixture of 1- methyl-4-nitro-2-trichloroacetylpyrrole (4.07 g, 15 mmol) and DIPEA (2 g, 16 mmol) in CH3CN. The mixture was stirred at 40 0C for 16 h, and then poured into ice. The precipitate formed was collected by filtration, washed with acetone and dried to provide 3.8 g (70% yield) as a mixture of two regioisomeric amides 28a and 28b in nearly 3: 1 ratio (as determined by 1H-NMR) as a light brown solid which was used for acid-promoted cyclization to compound 27 as described in the following paragraph. 1H NMR (DMSO-d6) δ 9.21 (br s, 0.75H), 8.96 (br s, 0.25H), 7.82-7.94 (m, 3H), 6.81-6.93 (m, IH), 6.32 (br s, 0.25 H), 6.1 1 (br s, 0.75H), 3.92, 3.88 (2s, 3H, Py-NCH3), 3.15 (m, 4H, CH2), 2.48 (m, 4H, CH2), 2.23, 2.21 (2s, 3H, NCH3).
  • 46
  • [ 120122-47-6 ]
  • [ 174775-48-5 ]
  • [ 344941-89-5 ]
YieldReaction ConditionsOperation in experiment
Commercially available ethyl 5-NITROBENZOFURAN-2-CARBOXYLATE 30 was HYDROGENATED on PD-C and ACYLATED using commercially available 4-NITRO-N-METHYL-2- TRICHLOROACETYL-PYRROLE 32 to form 33. HYDROGENATION of 33 followed by acylation with 32 afforded the nitro compound 35, which upon HYDROGENATION yielded 36 as the amino compound. ACETYLATION of the amino group of 36 followed by base catalyzed hydrolysis resulted in the acid 37. Coupling of 37 with the hydrochloride salt 39 (obtained by DEPROTECTION of the BOC derivative 38) using EDC afforded the ester 40. See Figure 4.
  • 47
  • [ 120122-47-6 ]
  • [ 13138-77-7 ]
YieldReaction ConditionsOperation in experiment
93% With ammonia In water; ethyl acetate at 0 - 20℃; Inert atmosphere;
81.5% With ammonium hydroxide In tetrahydrofuran for 2h;
  • 48
  • [ 64-17-5 ]
  • [ 120122-47-6 ]
  • [ 2853-29-4 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine at 20℃; for 2h; 3.A Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate 0.50 g (1.84 mmol) of 1-methyl-4-nitro-2-trichloroacetyl-1H-pyrrole are initially charged in 5 ml of ethanol, 0.26 ml (1.84 mmol) of triethylamine are added and the mixture is stirred at RT for 2 h. 5 ml of water are added, the reaction mixture is stirred at 0° C. for 30 min and the precipitate is then filtered off with suction and dried under reduced pressure.Yield: 321 mg (88% of theory)LC-MS (Method 3): Rt=2.25 min.; MS (ESI+): m/z=119 (M+)1H-NMR (300 MHz, DMSO-d6): δ=8.29 (d, 1H), 7.31 (d, 1H), 4.27 (q, 2H), 3.92 (s, 3H), 1.30 (t, 3H).
  • 49
  • [ 120122-47-6 ]
  • tert-butyl 4-aminobutanoate hydrochloride [ No CAS ]
  • [ 1335228-78-8 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In ethyl acetate at 20℃; Inert atmosphere; 4.1.4. Ethyl 4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)butanoate (4a) General procedure: Compound 3 (10.1 g, 0.037 mol) was placed in a 500 mL round bottom flask and dissolved in 75 mL of dry EtOAc. Ethyl 4-amino-butyrate hydrochloride (9.35 g, 0.058 mol) was added to the flask. Dry TEA (15.05 mL, 0.108 mol) was added to the flask dropwise over 1 h. The reaction mixture was stirred under a nitrogen atmosphere. When TLC (EtOAc) indicated that 3 was absent, the solution was filtered by vacuum filtration to remove the white solid precipitate that was present. The filtrate was transferred to a 500 mL separatory funnel, and the organic layer was washed with 1 M HCl (2 × 100 mL), DI H2O (1 × 100 mL), 5% NaHCO3 (2 × 100 mL), and DI H2O (1 × 100 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. The residue was placed under vacuum for 24 h to yield 4a as a yellow solid (8.44 g, 80% yield).
  • 50
  • [ 120122-47-6 ]
  • [ 28494-50-0 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate In tetrahydrofuran; water at 0℃;
63% With hydrazine hydrate In ethanol at 20℃; for 1h; Inert atmosphere; General procedure for synthesis of 4-nitro-1H-pyrrole-2-carbohydrazide 4a and 4-nitro-1-methyl-pyrrole-2-carbohydrazide 4b: [11,24] General procedure: In a round bottom flask, equipped with sealed mechanical stirrer, 1mol of trichloroethanone 3a or 3b derivative was added in 30 mL of ethanol and stirred until the entire solution becomes homogeneous. To above mixture 2.5 equivalents (3-4 mL) Hydrazine hydrate (99%v/v) was added and stirred at room temperature till precipitate starts to appear. The whole reaction mixture was poured over crushed ice. The obtained solid precipitate was filtered by vacuum and dried. The precipitate was washed with hexane and recrystallized from absolute alcohol.
With hydrazine 2.7.1. Synthesis of (E)-N0-(2-hydroxybenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide (H21) 1-Methyl-4-nitro-1H-pyrrole-2-carbohydrazide (0.92 g,5 mmol) was dissolved in THF (50 ml). Salicylaldehyde (500 lL,5 mmol) was added to the above solution, and the mixture wasstirred at room temperature. The light yellow precipitate wasformed in solution, and the mixture was further stirred at roomtemperature for 5 h. The precipitate was collected and washedthree times with THF. Recrystallization from hot MeOH and dryingin vacuum afforded a yellowish solid. Yield was 1.31 g (91%).
With hydrazine hydrate In ethanol at 20℃; for 2h;
With hydrazine hydrate In ethanol at 20℃; for 2h; Inert atmosphere;

  • 51
  • [ 120122-47-6 ]
  • [ 121148-01-4 ]
  • [ 1373283-32-9 ]
  • 52
  • [ 120122-47-6 ]
  • [ 121148-00-3 ]
  • [ 1373283-33-0 ]
  • 53
  • [ 120122-47-6 ]
  • [ 1007859-81-5 ]
  • [ 1007859-91-7 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: tert-butyl 3-(1-Methyl-4-nitro-1H-pyrrole-2-carboxamido)propanoate With palladium 10% on activated carbon; hydrogen In ethanol for 2h; Stage #2: 1-methyl-4-nitro-2-trichloroacetylpyrrole In ethyl acetate at 20℃; for 48h;
  • 54
  • [ 4244-84-2 ]
  • [ 120122-47-6 ]
  • [ 1007859-81-5 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In ethyl acetate; at 20℃; for 63h;Inert atmosphere; Nitropyrrole 2 (30.00 g, 0.11 mol) was takenin a 500 mL round-bottom one-neck flask followed by additionof beta-alanine tert-butyl ester hydrochloride (17.05, 0.11 mol)and EtOAc (100 mL) that had been dried over sieves. TEA(35.5 mL, 0.25 mol) was dissolved in EtOAc (50 mL) driedover sieves, and this mixture was added dropwise to thereaction mixture, while being stirred over a period of 15 hunder a nitrogen atmosphere. The reaction mixtur was thenstirred for an additional 48 h, during which a white precipitatewas formed. The precipitate was removed by filtration, and thefiltrate was washed with 1 M HCl (2 × 100 mL) and DI water(1 × 100 mL). The organic layer was then dried over MgSO4and filtered and the solution concentrated by rotaryevaporation to give 10 as a yellow solid (0.197 g, 90percent yield).Mp: 103?105 °C. TLC (EtOAc): Rf = 0.66. 1H NMR (DMSOd6):delta 7.53 (d, J = 1.6 Hz, 1H), 7.05 (d, J = 1.6 Hz, 1H), 6.83 (t,J = 5.6 Hz, 1H), 3.95 (s, 3H), 3.56 (t, J = 6.4 Hz, 2H), 2.50 (t, J= 6.4 Hz, 2H), 1.42 (s, 9H). 13C NMR: delta 171.29, 159.67,134.28, 126.14, 125.80, 106.39, 80.83, 37.27, 34.50, 34.33,27.50. IR: 3408.5, 3347.2, 3147.8, 3135.2, 3123.5, 3116.2,3000.8, 2978.1, 2945.8, 1722.5, 1647.9, 1547.8, 1523.7, 1497.2,1417.3, 1368.3, 1311.1, 1267.7, 1221.3, 1151.5, 1111.7, 986.4,901.5, 873.8, 856.5, 842.6, 832.9, 821.5, 750.6, 596.3, 557.1.HRMS (ESI): m/z for C13H19N3O5 [M + Na]+ calcd 320.1217,found 320.1216.
  • 55
  • [ 120122-47-6 ]
  • [ 152916-77-3 ]
  • [ 152916-79-5 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: ethyl β-(1-methyl-4-nitropyrrole-2-carboxamido)alaninate With palladium 10% on activated carbon; hydrogen In ethanol Stage #2: 1-methyl-4-nitro-2-trichloroacetylpyrrole In ethyl acetate at 20℃; for 48h; Ethyl 3-[1-Methyl-4-(1-methyl-4-nitro-1H-pyrrol-2-carboxamido)-1H-pyrrole-2-carboxamido]propanoate (4) Compound3 (13.0 g, 48.3 mmol) was added to 95% EtOH (50mL) in a 500 mL Parr jar. Wet palladium on carbon (10%, 2.50g) was added to this mixture and the mixture shaken on ahydrogenation apparatus under pressurized hydrogen (70 psi).Once TLC (EtOAc) indicated that no starting material waspresent, the reaction mixture was filtered through Celite. TheCelite was washed with ethanol (2 × 50 mL), and the solventwas removed by rotary evaporation. The resulting pale yellowsolid was placed under vacuum for 24 h. Then, this solid andcompound 2 (14.50 g, 53.0 mmol) were dissolved in EtOAc(250 mL, dried over sieves) in a 500 mL round-bottom flask.The mixture was then allowed to stir for 48 h, during whichtime a yellow precipitate formed. After the reaction wascomplete as determined by TLC (EtOAc), the precipitate wasfiltered and placed under vacuum to yield pure 4 as a yellowsolid (28.20 g, 94% yield). Mp: 199-202 °C. TLC (EtOAc): Rf = 0.64. 1H NMR (DMSO-d6): δ 10.26 (s, 1H), 8.18 (d, J = 1.6Hz, 1H), 8.06 (t, J = 5.6 Hz, 1H), 7.59 (d, J = 1.6 Hz, 1H), 7.23(d, J = 1.6 Hz, 1H), 6.85 (d, J = 1.6 Hz, 1H), 4.10 (q, J = 7.2Hz, 2H), 3.96 (s, 3H), 3.82 (s, 3H), 3.42 (q, J = 7.2, 5.6 Hz,2H), 2.56 (t, J = 7.2 Hz, 2H), 1.21 (t, J = 7.2 Hz, 3H). 13CNMR: δ 171.84, 161.64, 157.31, 134.23, 128.68, 126.74, 123.42,121.81, 118.57, 108.01, 104.58, 60.36, 37.93, 36.50, 35.28,34.46, 14.56. IR: 3404.4, 3372.1, 3115.1, 2993.5, 2950.9,1712.3, 1670.5, 1642.7, 1580.7, 1563.4, 1520.5, 1496.6, 1465.6,1435.7, 1415.2, 1400.7, 1385.5, 1306.6, 1250.3, 1216.4, 1200.9,1159.8, 1143.5, 1120.1, 1093.5, 1074.2, 1025.5, 986.5, 865.2,815.3, 805.7, 770.7, 755.3, 667.8, 643.8, 609.2, 597.4. HRMS(ESI): m/z for C17H21N5O6 [M + H]+ calcd 392.1565, found392.1565.
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