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USD 0.00
Limited Quantity
USD 15-60
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USD 80+
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Structure of 290-37-9 * Storage: {[proInfo.prStorage]}
* 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.
Reference:
[1] Research on Chemical Intermediates, 2012, vol. 38, # 8, p. 1743 - 1750
3
[ 290-37-9 ]
[ 2423-65-6 ]
Yield
Reaction Conditions
Operation in experiment
88%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 16 h;
General Procedure 1:; Diazine Oxidation;The appropriate diazine (1 equiv.) and mCPBA (1 equiv.) were dissolved in DCM (0.2 M). The reaction was allowed to stir for 16 hours. PPh3 (0.5 equiv.) was then added to reduce any unreacted peracid and the mixture was stirred for an additional 4 h. The volatiles were evaporated under reduce pressure and the residue was purified via silica gel column chromatography.; Pyrazine N-oxide (80) Synthesised according to general procedure 1. Purification via silica gel column chromatography using 100percent EtOAc then a mixture of 20percent MeOH/EtOAc gave a white solid (88percent). 1H NMR (300 MHz, CDCl3, 293K, TMS): δ 8.50 (2H, d, J=3.9 Hz), 8.14 (2 H, d, J=4.8 Hz).13C NMR (75 MHz, CDCl3, 293K, TMS): 147.8, 134.0.HRMS calculated for C4H4N2O1 (M+) 96.0324; Found: 96.0295.Melting point ° C.: 103.2-104.5IR (vmax/cm-1): 3120, 3088, 1595, 861, 847, 838.Rf (20percent MeOH/EtOAc): 0.3
50%
With dihydrogen peroxide; acetic acid In water at 70 - 80℃; for 5.5 h;
A solution of pyrazine (2.5 g, 31 mmol) in AcOH (30 mL) was stirred at 70-80 °C while a mixture of 30percent H2O2 (3.55 g, 32 mmol) and AcOH (25 mL) was added dropwise over 30 min. After the addition, heating was continued for 5 h then the mixture was evaporated under reduced pressure and the residue was taken up in CH2Cl2 (125 mL). Drying over anhydrous Na2CO3 and evaporation gave a solid, which was recrystallised from hexane to give the title product (1.48 g, 50percent) as colourless crystals, mp 113-114 °C (lit.6 113-114 °C); δH 8.11 (2H, m) and 8.48 (2H, m).
Reference:
[1] Organic Letters, 2017, vol. 19, # 18, p. 4707 - 4709
[2] Organic Letters, 2018, vol. 20, # 8, p. 2346 - 2350
[3] Angewandte Chemie - International Edition, 2006, vol. 45, # 46, p. 7781 - 7786
[4] Patent: US2008/132698, 2008, A1, . Location in patent: Page/Page column 17-18
[5] Chemical Communications, 2015, vol. 51, # 12, p. 2425 - 2428
[6] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1585 - 1588
[7] Chemistry - A European Journal, 2013, vol. 19, # 44, p. 14998 - 15003
[8] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 5, p. 1386 - 1394
[9] Heterocyclic Communications, 2001, vol. 7, # 4, p. 307 - 312
[10] Tetrahedron, 2012, vol. 68, # 29, p. 5845 - 5851
[11] Journal of Organic Chemistry, 1958, vol. 23, p. 1603,1605
[12] Journal of the American Chemical Society, 1959, vol. 81, p. 5160,5163
[13] Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2059 - 2066
Reference:
[1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1285 - 1287
7
[ 110-85-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 109-97-7 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[6] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
8
[ 107-15-3 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[4] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
9
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
10
[ 110-85-0 ]
[ 288-32-4 ]
[ 290-37-9 ]
[ 616-47-7 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
Reference:
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
11
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 13925-00-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
12
[ 123-84-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
[ 15707-23-0 ]
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
13
[ 56-45-1 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 13925-03-6 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 4332 - 4335
14
[ 492-62-6 ]
[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
15
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
16
[ 290-37-9 ]
[ 127-17-3 ]
[ 22047-25-2 ]
Reference:
[1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 - 2869
17
[ 290-37-9 ]
[ 75-07-0 ]
[ 22047-25-2 ]
Reference:
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 17, p. 3288 - 3296
18
[ 290-37-9 ]
[ 75-07-0 ]
[ 22047-25-2 ]
[ 39248-49-2 ]
Reference:
[1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 497 - 500
19
[ 56-87-1 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 22047-25-2 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
20
[ 56-45-1 ]
[ 56-87-1 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 22047-25-2 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13360-64-0 ]
Reference:
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
21
[ 109-08-0 ]
[ 290-37-9 ]
[ 19847-12-2 ]
[ 98-96-4 ]
Reference:
[1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
22
[ 107-15-3 ]
[ 56-81-5 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 6705-33-5 ]
[ 108-50-9 ]
[ 5780-66-5 ]
Reference:
[1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8
23
[ 107-15-3 ]
[ 56-81-5 ]
[ 290-37-9 ]
[ 6705-33-5 ]
Reference:
[1] Applied Catalysis A: General, 2014, vol. 469, p. 398 - 409
24
[ 290-37-9 ]
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]
Reference:
[1] Patent: US2540476, 1948, ,
25
[ 103150-78-3 ]
[ 290-37-9 ]
[ 98-97-5 ]
Reference:
[1] Chemische Berichte, 1893, vol. 26, p. 724
26
[ 122-05-4 ]
[ 290-37-9 ]
[ 98-97-5 ]
[ 15719-64-9 ]
Reference:
[1] Chemische Berichte, 1893, vol. 26, p. 724
27
[ 89-01-0 ]
[ 290-37-9 ]
[ 98-97-5 ]
Reference:
[1] Chemische Berichte, 1907, vol. 40, p. 4852
[2] Chemische Berichte, 1907, vol. 40, p. 4852
28
[ 290-37-9 ]
[ 77287-34-4 ]
[ 98-96-4 ]
Yield
Reaction Conditions
Operation in experiment
86%
at 70℃; for 12 h;
General procedure: In an oven dried glass tube containing a mixture of pyridine 1a (100 mg, 1.26 mmol), and potassium persulphate (683 mg, 2.53 mmol), formamide 2a (2 ml) was added and the reaction mixture was heated at 70 °C. Upon the completion of the reaction (monitored by TLC), saturated sodium bicarbonate solution (5 mL) was added and the crude product was extracted in ethyl acetate (3 X 5 mL). The crude product was purified by column chromatography to furnish compound 3aa as a white crystalline solid (122 mg, 79percent yield)
Reference:
[1] Tetrahedron Letters, 2017, vol. 58, # 50, p. 4709 - 4712
[2] Tetrahedron, 1985, vol. 41, # 19, p. 4157 - 4170
[3] Chemical Communications, 2002, # 21, p. 2496 - 2497
Reference:
[1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
32
[ 290-37-9 ]
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]
Reference:
[1] Patent: US2540476, 1948, ,
33
[ 290-37-9 ]
[ 98-80-6 ]
[ 3438-48-0 ]
[ 7431-45-0 ]
Yield
Reaction Conditions
Operation in experiment
50 mg
With ammonium peroxodisulfate; zinc trifluoromethanesulfonate; silver nitrate In dichloromethane; water at 20℃; for 4 h;
General procedure: Ammonium persulfate (3 equiv, 342 mg), phenylboronic acid (1.5 equiv, 91 mg), silver nitrate (0.2 equiv, 17 mg), and zinc trifluoromethanesulfonate (0.2 equiv, 36 mg) were combined ina 10 mL round bottom flask. A heterocycle (1 equiv, 0.5 mmol) was then added to the same flask and solvated with water (0.4 mL) and CH2Cl2 (1.6 mL). The resulting mixture was sonicated for 10 sec and placed on a stir plate to stir vigorously at room temperature for 4 h. The reaction was quenched with 28percent ammonium hydroxide (2 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3 x 10 mL). The organic layer was dried over sodium sulfate, filtered through cotton, and evaporated en vacuo. The products were purified by column chromatography (SiO2, 5-20percent EtOAc/hexanes). Products 3b, 3c, and 3d required further purification by crystallization as the trifluoromethanesulfonic acid salts and recrystallization from THF/hexanes.
Reference:
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
58
[ 290-37-9 ]
[ 56842-95-6 ]
Reference:
[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 40, p. 9485 - 9489
59
[ 290-37-9 ]
[ 75-07-0 ]
[ 94777-52-3 ]
Reference:
[1] Journal of Organic Chemistry, 1995, vol. 60, # 12, p. 3781 - 3786
60
[ 290-37-9 ]
[ 128796-39-4 ]
[ 380626-88-0 ]
Reference:
[1] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2639 - 2648
With dipotassium peroxodisulfate; at 70℃; for 12h;
General procedure: In an oven dried glass tube containing a mixture of pyridine 1a (100 mg, 1.26 mmol), and potassium persulphate (683 mg, 2.53 mmol), formamide 2a (2 ml) was added and the reaction mixture was heated at 70 C. Upon the completion of the reaction (monitored by TLC), saturated sodium bicarbonate solution (5 mL) was added and the crude product was extracted in ethyl acetate (3 X 5 mL). The crude product was purified by column chromatography to furnish compound 3aa as a white crystalline solid (122 mg, 79% yield)
2,2',2"-cyclohexane-1,3,5-triyltripyrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
28%
With ammonium peroxydisulfate; sulfuric acid; silver nitrate; In water; at 80℃; for 0.5h;
Example 1 - Procedure for Tri-directional Radical Alkylation (Minisci-type) Reaction[0059] The results demonstrated below are believed to represent the first success in preparing tri-podal compounds using a tridirectional Minisci-type radical alkylation reaction. Because this procedure provides functional organic molecules in a single step, it fulfills many criteria of an ideal synthesis.[0060] To a solution of 1,3,5-cyclohexane tricarboxylic acid (1 mmol) in 10%H2SO4 (5 ml) was added silver nitrate (0.6 mmol) and the N-heterocycle (10 mmol). The reaction mixture was heated to 80 0C. A saturated solution of ammonium persulfate (10 mmol) in water was added dropwise over 10 minutes to the reaction mixture with evolution of carbon dioxide (indicated by bubbling in the solution). After emission of carbon dioxide ceased, the reaction mixture was allowed to stir for an additional 20 min at 80 0C. The reaction mixture was then poured into ice and neutralized using saturated ammonium hydroxide solution (q.s). The resulting suspension was extracted with chloroform and the organic extract was washed with brine solution. Finally, the organic layer was dried over Na2SO4 and concentrated to yield crude product. The crude product was then purified using flash chromatography (appropriate proportions of methanol and dichloromethane). [0061] Initial trials employing pyridine (Figure 4) as the radical acceptor and c-l,3,5-cyclohexanetricarboxylic acid reacted under modified Minisci conditions (1.0 eq. triacid, 0.6 eq. AgNO3, 10 eq. NH4S2Os, 10 eq. heterocyclic base, excess H2SO4) produced inseparable mixtures of regioisomeric products. Since both the pyridine 2- and 4-positions are available for reaction with the intermediate secondary radical, this outcome was not altogether surprising. In contrast, reaction with pyrazine under analogous conditions produced the desired (2,2',2") trisubstituted compound 2 in 24% isolated yield as the major product (Figure 4). Yield of the major product was strongly dependent on the use of an excess of heterocyclic base in the reaction, and one could envision further improvements by employing an even larger amount. However, difficulty with separating unreacted starting material as well as the <n="18"/>expense of the reagent itself must be balanced against the desire to optimize yields, and it was discovered that a 10-fold excess represented a reasonable compromise. [0062] The scope of this reaction was then examined by varying the identity of the heterocyclic base while keeping the radical source constant. As shown in Figure 4, yields of major products were remarkably consistent for reaction with pyrimidine (affording Compound 3), ethyl isonicotinate (affording Compound 5), and ethyl nicotinate (affording Compound 6). In contrast, reaction with pyridazine (affording Compound 4) produced only a 5% yield of the desired product. No reaction was observed with triazine or benzoxazole. Like pyridine, reaction with quinoline produced only a complex mixture of inseparable products.[0063] Compound 7 was synthesized because it was expected that this compound would allow monitoring of carbohydrate binding by fluorescence spectroscopy (the quinoline moiety is a known fluorophore). The synthesis was effected in a similar way as that of Compound 12, where c-cyclohexane 1,3,5- tricarboxylic acid was reacted with 4-methylquinoline in a tri-directional Minisci reaction to obtain Compound 7 in 5% yield. Studies by Minisci and co workers demonstrated that radical alkylation of lepidine proceeds more rapidly in nonpolar solvent (Minisci et al., J. Org. Chem. 52:730-736 (1987), which is hereby incorporated by reference in its entirety), and it is possible that a similar change in solvent environment could improve the yield of Compound 7.[0064] Regioselectivity for the reaction with ethyl nicotinate was particularly interesting; Compound 6 was the only product isolated with a mixed (4,4',6") configuration. A minor product was also produced in this reaction, but could not be isolated in sufficient quantity to permit characterization. [0065] The obtained products 2-7 were characterized as set forth below:2,2',2"-cyclohexane-l,3,5-triyltripyrazine (2): yellow, amorphous solid; yield: 28%; mp 122-124 0C. IR (thin film from CHCl3): 2922, 1576, 1523, 1472, 1406, 1248, 1152, 1058, 1016, 843, 767 cm"1. 1H NMR (400 MHz, CDCl3): delta 8.57 (d, J=0.8 Hz, 3H), 8.51 (t, J=I.2 Hz, 3H), 8.43 (d, J=2.0 Hz, 3H), 3.28-3.21 (m, 3H), 2.32 (d, J=IO Hz, 3H), 2.12 (q, J=IO Hz, 3H). 13C NMR (400 MHz, CDCl3): delta 159.6, 144.1, 143.5, 142.9, 43.5, 37.0. HRMS: m/z calcd for C18Hi9N6 (M+H)+: 319.1671; found: 319.1679.
24%
With dihydrogen peroxide; iron(II) sulfate; In dichloromethane; water; at 0℃; for 0.5h;Product distribution / selectivity;
Example 2 - Biphasic Variant of Tri-directional Minisci-type Reaction forSynthesis of 2,2 ',2"-cyclohexane-l,3,5-triyltripyrazine (Compound2); [0066] A biphasic variant of the traditional Minisci reaction, reported byHeinisch and Ltsch (Angew. Chem. Int. Ed. 24:692-693 (1985), which is hereby incorporated by reference in its entirety), was examined using pyrazine as the radical acceptor (Scheme 3; Figure 3). Cyclohexane tricarboxylic acid (leq.) was reacted with pyrazine (10 eq.) and ferrous sulfate heptahydrate (10 eq.) in a hydrogen peroxide (aq.) / dichlormethane biphasic solution at 00C for 15 minutes. After 15 min. of stirring, the resulting mixture was poured into ice, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (3 times, 5 ml). After drying over anhydrous Na2SO4, the solvent was removed in vacuo to generate a yellow oil. This oil was directly applied to silica gel and eluted with a 5% MeOH/CH2Cl2 solution to afford the desired compound (2) in 24% yield. Increases in reaction time did not result in an increase in yield.
[Cu(3-hydroxy-2-quinoxalinecarboxylate)2(py)]*4H2O}[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Ca. 40%
To a stirred solution of Cu(ClO4)2*6H2O (18.75 mg, 0.05mmol) in H2O (2 mL) was added 1 equiv. of pyrazine (4 mg,0.05 mmol) in CH3OH (5 mL). This was stirred for 5 min,and then a 5 mL CH3OH solution of <strong>[1204-75-7]3-hydroxy-2-quinoxalinecarboxylic acid</strong> (9.5 mg, 0.05 mmol) wasadded to the reaction mixture and then filtered to givea green solution. Slow evaporation of the solvent atroom temperature gave rise to green block single crystals suitable for X-ray single-crystal analysis after ca 5 days. Yield: 40% (based on Cu). Anal. calcd forC22H20CuN6O10: C, 44.64; H, 3.41; N, 14.20%. Found: C,44.58; H, 3.49; N, 14.27%; IR (KBr)/cm-1: 3464(m),1683(s), 1609(m), 1374(m), 1326(m), 1221(w), 986(w),882(w), 806(w), 776(m), 676(m), 446(w).
Example 2 Preparation and Characterization of the Co-Crystal <strong>[287714-41-4]Rosuvastatin</strong> Pyrazine Hydrate of Formula (IV) [0087] Preparation [0088] To an assay tube equipped with magnetic stirrer containing <strong>[287714-41-4]Rosuvastatin</strong> (as acid form) (31 mg, 0.06 mmol) and pyrazine (250 mg, 3.1 mmol, 50 eq), water was added (0.3 mL) and the mixture was sonicated for 5 min before stirring for 3 h at room temperature. The resulting white suspension was centrifuged at room temperature (14000 rpm, 10 min), the supernatant liquid was discarded and the resulting solid was dried at vacuum to provide 17 mg of co-crystal <strong>[287714-41-4]Rosuvastatin</strong> pyrazine hydrate as a white solid for a molar yield of 50%. 1H-NMR Characterization [0089] Proton nuclear magnetic resonance analyses were recorded in deuterated dimethyl sulfoxide (DMSO-d6) in a Varian Mercury 400 spectrometer, equipped with a broadband probe ATB 1H/19F/X of 5 mm. Spectra were acquired dissolving 5-10 mg of sample in 0.6 mL of deuterated solvent. [0090] 1H-NMR (DMSO, 400 MHz): delta=8.66 (s, 4H); 7.77-7.67 (m, 2H); 7.33-7.23 (m, 2H); 6.51 (dd, J=1.2 Hz, J=16.0 Hz, 1H); 5.54 (dd, J=5.9 Hz, J=16.0 Hz, 1H); 4.20 (q, J=6.3 Hz, 1H); 3.89-3.78 (m, 1H); 3.55 (s, 3H); 3.50-3.39 (m, 4H); 2.31 (dd, J=4.7 Hz, J=14.8 Hz, 1H); 2.20 (dd, J=7.8 Hz, J=14.8 Hz, 1H); 1.60-1.49 (m, 1H); 1.45-1.34 (m, 1H); 1.22 (d, J=6.6 Hz, 6H). (See FIG. 6-1H-NMR) Karl-Fischer Characterization [0091] Karl Fischer analyses were recorded with a Metrohm 787 KF Trinito. Analyses of two samples of 28.1 mg and 36.8 mg were carried out using the following reactants: Hydranal-Composite 5 (Riedel de Haen Ref 34081), Hydranal Methanol Rapid (Riedel de Haen Ref 37817) and Hydranal Water Standard 10.0 (Riedel de Haen Ref 34849 used to calculate the factor). [0092] The KF analysis of the co-crystal <strong>[287714-41-4]Rosuvastatin</strong> pyrazine hydrate shows 3.6% water (average of the two analyses) confirming that such co-crystal is a monohydrate form (calc. 3.1%). X-Ray Powder Diffraction (XRPD) Characterization [0093] XRPD analysis was performed using a Philips X?Pert diffractometer with Cu Kalpha radiation in Bragg-Brentano geometry. The system is equipped with a mono-dimensional, real time multiple strip detector. The diffractogram was recorded from 3 to 40 (20) at a scan rate of 17.6 per minute (See FIG. 7). [0094] List of selected peaks (only peaks with relative intensity greater than or equal to 1% are indicated) in Table 5:
In water; at 375℃; under 760.051 Torr; for 6h;Inert atmosphere; Flow reactor;
The dehydrocyclization activities of Zn?Cr?Ocatalysts calcined at different temperatures were performedat 375°C and atmospheric pressure in a fixedbedvertical quartz reactor (i.d = 8 mm, length =450 mm) placed in a two zone furnace operated in adown flow mode. In the first zone maintained at300°C the reaction mixture was preheated whereas inthe second zone containing the catalyst bed the reactortemperature was set at 375°C. Temperatures in theboth zones were monitored by a temperature controller-cum-programmer using a K-type thermocouple.Glycerol (Fluka) and EDA (SDFCL, India) wereused. Nitrogen (IOLAR-I grade, BOC, India) wasused as a carrier gas. The catalytic activities were measured using ?18/+23 sieved (BSS) particles. The carbonmass balance was done based on the inlet and outletconcentration of the organic moiety. Prior to thereaction, the calcined catalyst (about 0.2 g) wasreduced in a flow of 5percent H2 and 95percent Ar (30 mL min?1)at 400°C for 5 h. The catalytic activities were measuredunder strict kinetic control. An aqueous glycerol solution(20 wtpercent in H2O) was used with a glycerol to EDAmole ratio of 1 :1 , at a flow rate of 5 mL h?1 (10 mmolglycerol + 10 mmol EDA + 200 mmol H2O), alongwith N2 as a carrier gas at a flow rate of 1800 mL h?1.The feed mixture mole ratio is glycerol : EDA : H2O :N2= 1 : 1 : 20 : 8. The product mixture was analyzed bygas chromatograph (Shimadzu, GC-17A) via a flameionization detector (FID) using a ZB-5 capillary columnat a ramping rate of 10°C min?1 from 60 to280°C. The mass balance for all the measurements was>95percent. The samples were analyzed by GC-MS(QP5050A Shimadzu) using a ZB-5 capillary columnwith EI mode.
A 250 ml round bottom flask was first placed in an ice-water bath followed by the addition of 0.01 mmol of pyrazine,0.05 mol acetaldehyde (dissolved in 15 ml of water), 15 ml of glacial acetic acid and 3 ml of concentrated sulfuric acid, stirring to completely dissolve pyrazine,And then continue to stir for 10 min, slowly dropping 0.02mmol of t-butyl hydroperoxide solution, after dripping and then continue to stir for 20 min, and finally slowly dropping the concentration of 0.02mol / L ferrous sulfate solution 1ml,After the completion of the dropwise stirring for 2 h, the mixture was filtered and washed with a large amount of water to obtain 2,5-dicarboxylic acid pyrazine.
Ag<SUB>4</SUB>(H<SUB>2</SUB>O)<SUB>2</SUB>(npth)<SUB>2</SUB>[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58.71%
With ammonia; In methanol; N,N-dimethyl-formamide; at 40℃; for 0.5h;Sonication;
A mixture of AgNO3 (33.4 mg, 0.2 mmol), pyrazine (pyz) (16.0 mg, 0.2 mmol) and <strong>[603-11-2]3-nitrophthalic acid</strong> (H2npth) (42.2 mg, 0.2 mmol) were dissolved in methanol-H2O-DMF (N,N-dimethylformamide) solvents (6 mL, v/v/v = 1:1:1) in the presence of ammonia (0.5 mL, 14 M) under ultrasonic treatment (160 W, 40 kHz, 30 min) at 40 C. The resultant colorless solution was allowed to evaporate slowly at room temperature in the dark. Colorless crystals of compound 1 were obtained after several days. The crystals were isolated by filtration, washed with deionized water and dried in air. Yield based on silver is 58.71%. Elemental analysis, anal. calc. (found) for Ag4C16H10N4O14: C, 21.64 (21.67); H, 1.14 (1.12); N, 3.20 (3.16)%. IR (KBr, cm-1): 3355 (m), 3099 (w), 1591 (vs), 1519 (m), 1461 (m), 1399 (s), 1343 (m), 1157 (w), 924 (w), 826 (w), 753 (m), 717 (m).
With ammonia; at 100℃; for 72h;Autoclave; High pressure;
A mixture of AgNO3 (33.4mg, 0.2mmol), H2npth (42.2mg, 0.2mmol), pyz (16mg, 0.2mmol) and H2O (10mL) was stirred for a few minutes, then sealed in a 25mL Teflon-lined stainless steel autoclave and heated at 100C for 72h. After cooling to room temperature, pale yellow crystals were obtained in a yield of 51.91% based on Ag. Elemental analysis, anal. calc. (found) for AgC12H10N3O7: C, 34.63 (34.61); H, 2.41 (2.40); N, 10.09 (10.10)%. IR (KBr, cm-1): 3443 (w), 3092 (w), 1720 (m), 1653 (s), 1630 (m), 1540 (vs), 1384 (s), 1348 (vs), 1151 (m), 784 (m), 707 (m).
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide; In dichloromethane; water; at 40℃;
General procedure: N-heteroarene (1 mmoL, 80 mg), alpha-keto acid (3 mmol), Formic acid (1 mmol, 38 muL), ammonium persulfate (3 mmoL, 685 mg), ferrous sulfate heptahydrate (0.08 mmoL, 22 mg) and 20 mL of mixed solvent (DCM: H2O = 3: 1) , 0.1 mL DMSO was added into a 25 mL round-bottomed flask. The mixture was stirred at 40 oC until TLC analysis indicating that the reaction was complete (witnessed by the disappearance of the N-heteroarene). After separation of organic phase, the residue was neutralized by 0.1 M sodium hydroxide solution, then extracted with DCM (3×20 mL), combined the organic phases, dried over Na2SO4, and concentrated in vacuo. The residue was N-heteroarene (1 mmoL, 80 mg), alpha-keto acid (3 mmol), Formic acid (1 mmol, 38 muL), ammonium persulfate (3 mmoL, 685 mg), ferrous sulfate heptahydrate (0.08 mmoL, 22 mg) and 20 mL of mixed solvent (DCM: H2O = 3: 1) , 0.1 mL DMSO was added into a 25 mL round-bottomed flask. The mixture was stirred at 40 oC until TLC analysis indicating that the reaction was complete (witnessed by the disappearance of the N-heteroarene). After separation of organic phase, the residue was neutralized by 0.1 M sodium hydroxide solution, then extracted with DCM (3×20 mL), combined the organic phases, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of petroleum ether/EtOAc (v : v = 20 : 1) as eluent to afford the desired pure product.