Home Cart 0 Sign in  

[ CAS No. 98-96-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 98-96-4
Chemical Structure| 98-96-4
Structure of 98-96-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 98-96-4 ]

Related Doc. of [ 98-96-4 ]

Alternatived Products of [ 98-96-4 ]

Product Details of [ 98-96-4 ]

CAS No. :98-96-4 MDL No. :MFCD00006132
Formula : C5H5N3O Boiling Point : -
Linear Structure Formula :- InChI Key :IPEHBUMCGVEMRF-UHFFFAOYSA-N
M.W : 123.11 Pubchem ID :1046
Synonyms :
Pyrazinoic acid amide;Pyrazinecarboxamide;NSC 14911;MK 56;α-Pyrazinamide;Aldinamide

Calculated chemistry of [ 98-96-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 30.13
TPSA : 68.87 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.74
Log Po/w (XLOGP3) : -0.6
Log Po/w (WLOGP) : -0.42
Log Po/w (MLOGP) : -1.66
Log Po/w (SILICOS-IT) : 0.08
Consensus Log Po/w : -0.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.65
Solubility : 27.4 mg/ml ; 0.223 mol/l
Class : Very soluble
Log S (Ali) : -0.37
Solubility : 51.9 mg/ml ; 0.422 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.2
Solubility : 7.82 mg/ml ; 0.0635 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 98-96-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98-96-4 ]

* 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.

  • Upstream synthesis route of [ 98-96-4 ]
  • Downstream synthetic route of [ 98-96-4 ]

[ 98-96-4 ] Synthesis Path-Upstream   1~36

  • 1
  • [ 98-96-4 ]
  • [ 5049-61-6 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 664
  • 2
  • [ 98-96-4 ]
  • [ 22047-25-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 7, p. 1093 - 1101
  • 3
  • [ 98-96-4 ]
  • [ 19847-12-2 ]
YieldReaction ConditionsOperation in experiment
85% at 325℃; for 1 h; General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), the stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is almost complete. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic proteomics and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10 and A-11 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99percent).In these nitrile product preparation examples, 10 g of diphosphorus pentoxide was optionally added to the reaction vessel as a catalyst at the start of the reaction.
34% With trichlorophosphate In acetonitrile for 6 h; Inert atmosphere; Reflux In a dried 500 ml, three necked, jacketed flask fitted with a mechanical stirrer, temperature probe, a reflux condenser, a circulation bath, and a positive nitrogen atmosphere set-up was charged with 2-pyrazinecarboxamide 20.0 gm (0.162 mol), acetonitrile 240 ml, and POCl3 59.6 gm (0.389 mol). The white slurry was agitated and heated to reflux. The reaction mixture was maintained at reflux for at least 6 hours. Then the excess POCl3 was distilled off under reduced pressure. After aqueous work up, the reaction mixture was extracted with 4.x.70 ml ethyl acetate. The combine ethyl acetate extracts were washed with 3.x.70 ml water, distilled under reduced pressure to remove ethyl acetate and to afford cyanopyrazine as a brown oil: 5.76 gm (34percent yield); HPLC purity, >98 area percent; 1H NMR (300 MHz, CDCl3) δ 8.67 (pair d, J=1.7 and 2.5 1H), 8.75 (d, J=2.5, 1H), 8.87 (d, J=1.3 1H); 13C NMR (300 MHz, CDCl3) δ 115.1, 130.7, 145.3, 147.3, 148.1.
Reference: [1] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 7, p. 1093 - 1101
[2] Patent: CN104557357, 2018, B, . Location in patent: Paragraph 0150; 0151; 0152; 0160
[3] Chemical Communications, 2007, # 3, p. 301 - 303
[4] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 10, p. 731 - 742
[5] Patent: US2009/292122, 2009, A1, . Location in patent: Page/Page column 12-13
[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 822
[7] Patent: US4442095, 1984, A,
[8] Patent: US4442097, 1984, A,
[9] Patent: US4442096, 1984, A,
  • 4
  • [ 109-08-0 ]
  • [ 290-37-9 ]
  • [ 19847-12-2 ]
  • [ 98-96-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
  • 5
  • [ 98-96-4 ]
  • [ 98-97-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 48, p. 9176 - 9179
[2] Journal of the Indian Chemical Society, 2013, vol. 90, # 2, p. 181 - 185
[3] Biocatalysis and Biotransformation, 2017, vol. 35, # 1, p. 74 - 85
[4] Journal of Molecular Structure, 2018, vol. 1173, p. 469 - 480
  • 6
  • [ 290-37-9 ]
  • [ 77287-34-4 ]
  • [ 98-96-4 ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 56423-63-3 ]
  • [ 15226-74-1 ]
  • [ 98-96-4 ]
YieldReaction ConditionsOperation in experiment
74% With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3 h; Sealed tube General procedure: To a stirred solution of aryl halide (Br/I) (1 mmol) in dry dioxane in a 25 mL sealed tube, was added Pd(OAc)2 (5 molpercent), dppf (6 mol percent), DIPEA (2 mmol), imidazole (0.25 mmol), ammonium chloride (2 mmol) and then Co2(CO)8 (0.3 mmol). The seal tube was closed immediately and stirred at 90 °C for 3h. After the reaction time the reaction mixture was cooled to room temperature. The reaction mixture was filtered through celite pad and washed with dioxane, the filtrate was concentrated under reduced pressure and the residue obtained was purified by column chromatography.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 34, p. 4864 - 4867
  • 8
  • [ 19847-12-2 ]
  • [ 98-96-4 ]
YieldReaction ConditionsOperation in experiment
98% at 100℃; for 0.333333 h; A solution of nitrile 3 in ethanol/H2O (0.6 M, 8:1 v/v) was passed through the column reactor R2 (100 mm × 10 mm, 5 g hydrous zirconia) heated at 100 °C, with a residence time of 20 minutes, to obtain a quantitative recovery of the primary amide 2 after concentration of the reactor output (>98percent yield). White solid; m.p. 191–194 °C; δ H (400 MHz, d6-DMSO, 25 °C) 7.84 (1H, br. s), 8.24 (1H, br. s), 8.70 (1H, dd, J = 2.5 Hz, J 1.5 Hz), 8.85 (1H, d, J = 2.5 Hz), 9.17 (1H, d, J = 1.5 Hz); δ C (100 MHz, CDCl3, 25 °C) 143.46 (CH), 143.69 (CH), 145.18 (C), 147.46 (CH), 165.13 (C); FTIR (neat, ν): 3422, 3132, 1669, 1583, 1525, 1481, 1432, 1373, 1171, 1089, 1046, 1021, 870, 791 cm−1; LC-MS: retention time 0.28 min, m/z [M + H]+ = 124.19; HRMS (ESI): m/z calcd for C5H6ON3+: 124.0505; found 124.0504. Elemental analysis: calcd C = 48.78percent, H = 4.09percent, N = 34.13percent; found C = 48.60percent, H = 4.19percent, N = 33.70percent.
96% at 110℃; for 6 h; General procedure: Two milli liter water at room temperature was added to astirred mixture of nitrile (1mmol) and catalyst (40mg) thenheated with an oil bath maintained at 110°C, and stirred. After completion of the reaction (monitored by TLC), thecatalyst was removed from the reaction mixture by externalmagnet. Then the mixture was extracted with ethyl acetate,subsequently purified by column chromatography on silicagel to provide the corresponding amide products.
65% With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In nitromethane; water at 20 - 80℃; for 0.25 h; To a nitromethane (0.10 mL) solution of pyrazine-2-carbonitrile (4e) (30 mg, 0.285 mmol) were addedH2O (1.0 mL), DBU (87 mg, 0.571 mmol), copper (I) iodide (11 mg, 0.0571 mmol), cesium (I)carbonate (47 mg, 0.143 mmol), 4-dimethylaminopyridine (35 mg, 0.285 mmmol) at roomtemperature. The reaction mixture was heated at 80 °C for 15 min and then poured into water (50mL). The organic layer was separated and the aqueous layer was extracted with AcOEt. Thecombined organic layer was dried over MgSO4. The solvent was removed under reduced pressure.The residue was purified by preparative TLC on silica gel eluting with AcOEt-n-hexane (2:1) to givepyrazine-2-carboxamide (5e) S11 (23 mg, 65percent) as pale yellow powders.5e: mp 187-188 °C,
92 %Chromat.
Stage #1: With dimethyl sulfoxide; sodium hydroxide In ethanol; water at 25℃; for 0.0416667 h; Flow reactor
Stage #2: With dihydrogen peroxide In ethanol; water at 25℃; for 0.0694444 h; Flow reactor
General procedure: 0.6 mmol benzonitrile and 0.6 mmol DMSO were solved in 3 mL EtOH and pumped into inlet A, 50 μL 1 M NaOH (aq) solved in 1 mL EtOH and pumped into inlet B, 30percent H2O2 (aq) was solved in 7 mL ethanol and pumped into inlet C (flow rate A: B: C = 1.54 μl/min:0.46 μl/min:0.3 μl/min for a 400s residence time). The whole system was maintained on 25 °C. The flow system was equilibrated for 30 min, then the product stream was quenched and collected in a glass vessel with saturated aqueous NaHSO3 in it for 2 h. After being filtered, 5.0 ml of this solution was injected to the HPLC instrument for analysis. The conversion of the reaction was determined by relative area percentage of nitriles and corresponding amides. Conversion = Area (benzamide)/[Area (benzamide) + Area (benzonitrile)].

Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 11, p. 2814 - 2819
[2] Organic Letters, 2014, vol. 16, # 4, p. 1060 - 1063
[3] Chemistry - A European Journal, 2017, vol. 23, # 32, p. 7761 - 7771
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 641 - 652
[5] ACS Catalysis, 2015, vol. 5, # 1, p. 20 - 26
[6] Chemical Communications, 2009, # 22, p. 3258 - 3260
[7] Organic Syntheses, 2017, vol. 94, p. 34 - 45
[8] New Journal of Chemistry, 2018, vol. 42, # 18, p. 15221 - 15230
[9] Catalysis Letters, 2018, vol. 148, # 11, p. 3378 - 3388
[10] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 4148 - 4151
[11] ChemSusChem, 2012, vol. 5, # 8, p. 1392 - 1396
[12] Applied Catalysis A: General, 2012, vol. 421-422, p. 114 - 120
[13] ChemSusChem, 2013, vol. 6, # 8, p. 1341 - 1344
[14] New Journal of Chemistry, 2016, vol. 40, # 1, p. 358 - 364
[15] Synthetic Communications, 2002, vol. 32, # 11, p. 1731 - 1734
[16] ACS Catalysis, 2014, vol. 4, # 6, p. 1901 - 1910
[17] Green Chemistry, 2014, vol. 16, # 4, p. 2136 - 2141
[18] Dalton Transactions, 2016, vol. 45, # 34, p. 13590 - 13603
[19] Green Chemistry, 2016, vol. 18, # 18, p. 4865 - 4870
[20] Synlett, 2018, vol. 29, # 15, p. 2061 - 2065
[21] Synthetic Communications, 2000, vol. 30, # 10, p. 1713 - 1718
[22] Chemistry - A European Journal, 2011, vol. 17, # 41, p. 11428 - 11431
[23] Inorganica Chimica Acta, 2016, vol. 442, p. 134 - 144
[24] Tetrahedron, 2018, vol. 74, # 13, p. 1527 - 1532
  • 9
  • [ 98-97-5 ]
  • [ 98-96-4 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 6, p. 2880 - 2892
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 315 - 318
[3] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 664
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1424 - 1427
[6] Patent: CN104557357, 2018, B, . Location in patent: Paragraph 0135; 0136; 0137; 0145
  • 10
  • [ 19847-10-0 ]
  • [ 98-96-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1424 - 1427
  • 11
  • [ 306990-94-3 ]
  • [ 98-96-4 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8210 - 8213
  • 12
  • [ 109-08-0 ]
  • [ 98-96-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1993, vol. 27, # 3, p. 219 - 220[2] Khimiko-Farmatsevticheskii Zhurnal, 1993, vol. 27, # 3, p. 45 - 47
  • 13
  • [ 19847-12-2 ]
  • [ 64-17-5 ]
  • [ 98-96-4 ]
  • [ 1339045-85-0 ]
  • [ 6924-68-1 ]
YieldReaction ConditionsOperation in experiment
65% Cooling with ice To a solution of pyrazinecarbonitrile (1.00 g, 9.5 mmol) in dry ethanol (30 ml) was introduced a stream of dry HCl gas bubbled through the solution with stirring. Shortly after the HCl was introduced the temperature quickly rose requiring cooling with an ice/water bath. At this time a heavy white precipitate had fonned and after 2 h the gas inlet was replaced with a calcium' chloride drying tube and the reaction mixture stirred overnight. The HC1 gas stream was re-introduced into the reaction mixture for 2 h before again replacing the gas inlet with a drying tube and stirring for 1 h. Dry diethyl ether (45 ml) was then added to the mixture and stirring continued for 10 min before the solid was filtered under nitrogen using a Schlenk apparatus. The collected material was washed with dry diethyl ether (3 x 20 ml) and dried under vacuum to give 1.59 g of a highly moisture- sensitive white powder. nmr revealed the solid to be a mixture of the desired ethyl pyrazine-2-carbimidate hydrochloride (65percent) and the two hydrolysis products pyrazine-2- carboxamide (30percent) and ethyl pyrazine-2-carboxylate (5percent).*H nmr (400 MHz, de-dmso) δ 1.49, t (J = 7.0 Hz), 3H, OEt; 4.73, q (J = 6.9 Hz), 2H, OEt; 7.85, br, lH, C=NH2+; 8.24, br, 1H, C=NH2+; 8.93, dd (J = 1.6, 2.4 Hz), 1H, H6; 9.06, d (J = 2.4 Hz), 1H, H5; 9.33, d (J = 1.2 Hz), 1H, H3.
Reference: [1] Patent: WO2011/123890, 2011, A1, . Location in patent: Page/Page column 63-64
  • 14
  • [ 123-32-0 ]
  • [ 98-96-4 ]
  • [ 41110-27-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
  • 15
  • [ 6164-79-0 ]
  • [ 98-96-4 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 664
[2] Yakugaku Zasshi, 1956, vol. 76, p. 470[3] Chem.Abstr., 1956, p. 14777
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 22, p. 622
[5] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
  • 16
  • [ 123-32-0 ]
  • [ 290-37-9 ]
  • [ 98-96-4 ]
  • [ 5521-57-3 ]
  • [ 41110-27-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
  • 17
  • [ 89-01-0 ]
  • [ 98-96-4 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 664
  • 18
  • [ 19847-12-2 ]
  • [ 98-96-4 ]
  • [ 32046-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 169 - 171
  • 19
  • [ 123-32-0 ]
  • [ 290-37-9 ]
  • [ 109-08-0 ]
  • [ 98-96-4 ]
  • [ 41110-27-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
[2] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
[3] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 7, p. 381 - 383
  • 20
  • [ 13925-00-3 ]
  • [ 98-96-4 ]
Reference: [1] Journal of Chemical Thermodynamics, 2005, vol. 37, # 1, p. 49 - 53
  • 21
  • [ 4744-50-7 ]
  • [ 98-96-4 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 470[2] Chem.Abstr., 1956, p. 14777
  • 22
  • [ 73763-86-7 ]
  • [ 98-96-4 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 470[2] Chem.Abstr., 1956, p. 14777
  • 23
  • [ 109-08-0 ]
  • [ 290-37-9 ]
  • [ 19847-12-2 ]
  • [ 98-96-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
  • 24
  • [ 67367-37-7 ]
  • [ 98-96-4 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 470[2] Chem.Abstr., 1956, p. 14777
[3] Patent: US2780624, 1953, ,
  • 25
  • [ 2423-84-9 ]
  • [ 77287-34-4 ]
  • [ 98-96-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 949 - 953
[2] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 949 - 953
  • 26
  • [ 89-01-0 ]
  • [ 57-13-6 ]
  • [ 98-96-4 ]
Reference: [1] Patent: US2705714, 1952, ,
  • 27
  • [ 98-96-4 ]
  • [ 768-05-8 ]
YieldReaction ConditionsOperation in experiment
80% With hydrazine hydrate In ethanol for 12 h; Reflux A mixture of pyrazine-2-carboxamide (1) 50 g (0.406 mol) in ethanol (500 mL) and hydrazine hydrate (98percent) 34.76 g (0.695 mol) was refluxed for 12 h. The completion of reaction was monitored by TLC (Hexane 6: Ethyl acetate 4). The reaction mass cooled to 10-15°C and filtered off under vacuum. Pyrazin-2-carboxamide is highly soluble in iso-octane at 25-30°C. Iso-octane (50 mL) washing given and suck dried to give pure white to off white solid compound (2) 41.50 g (80.00percent) mp-168-170°C. IR (KBr, cm-1): 3352.4 (-NH2 stretch), 3230.3 (>NH stretch), 2845 (-OCH3), 1640.65 (>C=O stretch), 764 (>C-Br); 1HNMR (400 MHz, DMSO-d6 ppm): δ 4.50 (s, 2H, amine), 8.59 (s, 1H, amide), 8.74 (d, 1H, CH-pyrazine), 9.16 (d, 1H, CH-pyrazine), 9.90 (s, 1H, C=NH); 13C NMR (400MHz, DMSO-d6 ppm): 143.36 (pyrazine C-N), 143.71 (pyrazine C=N), 144.74 (pyrazine C=N), 147.38 (pyrazine C=N), 162.10 (-C=O). MS: 137; m/z: 138 (M+H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3845 - 3850
  • 28
  • [ 19847-12-2 ]
  • [ 64-17-5 ]
  • [ 98-96-4 ]
  • [ 1339045-85-0 ]
  • [ 6924-68-1 ]
YieldReaction ConditionsOperation in experiment
65% Cooling with ice To a solution of pyrazinecarbonitrile (1.00 g, 9.5 mmol) in dry ethanol (30 ml) was introduced a stream of dry HCl gas bubbled through the solution with stirring. Shortly after the HCl was introduced the temperature quickly rose requiring cooling with an ice/water bath. At this time a heavy white precipitate had fonned and after 2 h the gas inlet was replaced with a calcium' chloride drying tube and the reaction mixture stirred overnight. The HC1 gas stream was re-introduced into the reaction mixture for 2 h before again replacing the gas inlet with a drying tube and stirring for 1 h. Dry diethyl ether (45 ml) was then added to the mixture and stirring continued for 10 min before the solid was filtered under nitrogen using a Schlenk apparatus. The collected material was washed with dry diethyl ether (3 x 20 ml) and dried under vacuum to give 1.59 g of a highly moisture- sensitive white powder. nmr revealed the solid to be a mixture of the desired ethyl pyrazine-2-carbimidate hydrochloride (65percent) and the two hydrolysis products pyrazine-2- carboxamide (30percent) and ethyl pyrazine-2-carboxylate (5percent).*H nmr (400 MHz, de-dmso) δ 1.49, t (J = 7.0 Hz), 3H, OEt; 4.73, q (J = 6.9 Hz), 2H, OEt; 7.85, br, lH, C=NH2+; 8.24, br, 1H, C=NH2+; 8.93, dd (J = 1.6, 2.4 Hz), 1H, H6; 9.06, d (J = 2.4 Hz), 1H, H5; 9.33, d (J = 1.2 Hz), 1H, H3.
Reference: [1] Patent: WO2011/123890, 2011, A1, . Location in patent: Page/Page column 63-64
  • 29
  • [ 98-96-4 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 30
  • [ 98-96-4 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 31
  • [ 98-96-4 ]
  • [ 36070-75-4 ]
Reference: [1] Agricultural and Biological Chemistry, 1982, vol. 46, # 8, p. 2169 - 2172
  • 32
  • [ 98-96-4 ]
  • [ 21279-64-1 ]
Reference: [1] Agricultural and Biological Chemistry, 1982, vol. 46, # 8, p. 2169 - 2172
  • 33
  • [ 2423-65-6 ]
  • [ 98-96-4 ]
  • [ 59489-39-3 ]
  • [ 55557-52-3 ]
Reference: [1] Patent: US4293552, 1981, A,
  • 34
  • [ 98-96-4 ]
  • [ 6863-74-7 ]
  • [ 36070-75-4 ]
  • [ 55557-52-3 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 1, p. 61 - 65
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1598 - 1601
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 476 - 479
  • 35
  • [ 2423-65-6 ]
  • [ 98-96-4 ]
  • [ 59489-39-3 ]
  • [ 55557-52-3 ]
Reference: [1] Patent: US4293552, 1981, A,
  • 36
  • [ 98-96-4 ]
  • [ 356783-16-9 ]
Reference: [1] Patent: CN106478528, 2017, A,
Same Skeleton Products
Historical Records