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Product Citations

Product Citations

Nicholas O. Schneider ; Kendra Gilreath ; Daniel J. Burkett , et al. DOI:

Abstract: Glycogen synthase kinase-3 (GSK-3) is a serine/threonine kinase which plays a center role in the phosphorylation of a wide variety of proteins, generally leading to their inactivation. As such, GSK-3 is viewed as a therapeutic target. An ever-increasing number of small organic molecule inhibitors of GSK-3 have been reported. Phenylmethylene hydantoins are known to exhibit a wide range of inhibitory activities including for GSK-3β. A family of fourteen 2-heterocycle substituted methylene hydantoins (14, 17–29) were prepared and evaluated for the inhibition of GSK-3β at 25 μM. The IC50 values of five of these compounds was determined; the two best inhibitors are 5-[(4′-chloro-2-pyridinyl)methylene]hydantoin (IC50 = 2.14 ± 0.18 μM) and 5-[(6′-bromo-2-pyridinyl)methylene]hydantoin (IC50 = 3.39 ± 0.16 μM). The computational docking of the compounds with GSK-3β (pdb 1q41) revealed poses with hydrogen bonding to the backbone at Val135. The 5-[(heteroaryl)methylene]hydantoins did not strongly inhibit other metalloenzymes, demonstrating poor inhibitory activity against matrix metalloproteinase-12 at 25 μM and against human carbonic anhydrase at 200 μM, and were not inhibitors for Staphylococcus aureus pyruvate carboxylase at concentrations >1000 μM.

Keywords: nitrogen heterocycles ; glycogen synthase kinase 3β ; computational docking

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Product Details of [ 1121-60-4 ]

CAS No. :1121-60-4 MDL No. :MFCD00006290
Formula : C6H5NO Boiling Point : -
Linear Structure Formula :- InChI Key :CSDSSGBPEUDDEE-UHFFFAOYSA-N
M.W : 107.11 Pubchem ID :14273
Synonyms :

Calculated chemistry of [ 1121-60-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.62
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.77
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : 0.89
Log Po/w (MLOGP) : -0.23
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.27
Solubility : 5.75 mg/ml ; 0.0537 mol/l
Class : Very soluble
Log S (Ali) : -0.64
Solubility : 24.7 mg/ml ; 0.231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.91
Solubility : 1.33 mg/ml ; 0.0124 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 1121-60-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P273-P272-P260-P270-P210-P271-P264-P280-P284-P302+P352-P370+P378-P391-P337+P313-P305+P351+P338-P362+P364-P333+P313-P301+P312+P330-P304+P340+P310-P403+P233-P403+P235-P405-P501 UN#:2810
Hazard Statements:H330-H302-H315-H319-H317-H411-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1121-60-4 ]

* 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 [ 1121-60-4 ]
  • Downstream synthetic route of [ 1121-60-4 ]

[ 1121-60-4 ] Synthesis Path-Upstream   1~39

  • 1
  • [ 1121-60-4 ]
  • [ 21035-59-6 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; sodium tetrahydroborate; methylamine In ethanol; dichloromethane 12-1)
Preparation of 2-(methylaminomethyl)pyridine
Methylamine gas was bubbled through the benzene solution(60 ml) of 10.7 g(100 mmol) of 2-pyridinecarboxaldehyde for 2 hours.
Benzene was distilled off under a reduced pressure and the residue was taken up in 40 ml of ethanol.
To the resulting solution was added 5.7 g of NaBH4 in three portions and the resulting mixture was stirred at room temperature for 8 hours.
To the reaction mixture was added 0.5N hydrochloric acid with care not to allow the pH below 6.
300 ml of dichloromethane was added thereto and the resulting solution was washed three times with 1M NaHCO3 solution of pH 10.
The organic layer was concentrated under a reduced pressure to give 10.4 g of the title compound(yield: 85percent).
1 H NMR(CDCl3) δ2.1(s, 1H), 2.5(s, 3H), 3.9(s, 2H), 7.1(t, 1H), 7.3(d, 1H), 7.6(t, 1H), 8.5(d, 1H)
85% With hydrogenchloride; sodium tetrahydroborate; methylamine In ethanol; dichloromethane 12-1)
Preparation of 2-(methylaminomethyl) pyridine
Methylamine gas was bubbled through the benzene solution(60ml) of 10.7g(100mmol) of 2-pyridinecarboxaldehyde for 2 hours.
Benzene was distilled off under a reduced pressure and the residue was taken up in 40ml of ethanol.
To the resulting solution was added 5.7g of NaBH4 in three portions and the resulting mixture was stirred at room temperature for 8 hours.
To the reaction mixture was added 0.5N hydrochloric acid with care not to allow the pH below 6.
300ml of dichloromethane was added thereto and the resulting solution was washed three times with 1M NaHCO3 solution of pH 10.
The organic layer was concentrated under a reduced pressure to give 10.4g of the title compound(yield: 85percent).
1H NMR(CDCl3) δ 2.1(s, 1H), 2.5(s, 3H), 3.9(s, 2H), 7.1(t, 1H), 7.3(d, 1H), 7.6(t, 1H), 8.5(d, 1H)
Reference: [1] Patent: US5587388, 1996, A,
[2] Patent: EP601486, 1994, A1,
[3] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 696 - 706
  • 2
  • [ 1121-60-4 ]
  • [ 74-89-5 ]
  • [ 21035-59-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 10245 - 10256
  • 3
  • [ 1121-60-4 ]
  • [ 593-51-1 ]
  • [ 21035-59-6 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
  • 4
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  • [ 3433-37-2 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 46, p. 8501 - 8503
  • 5
  • [ 110-89-4 ]
  • [ 1121-60-4 ]
  • [ 536-74-3 ]
  • [ 531-67-9 ]
  • [ 5337-53-1 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 90, p. 87066 - 87081
  • 6
  • [ 1121-60-4 ]
  • [ 4985-92-6 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 19, p. 9805 - 9815
  • 7
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  • [ 141-82-2 ]
  • [ 7340-22-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 1989, vol. 24, p. 65 - 72
  • 8
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  • [ 1452-63-7 ]
Reference: [1] Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2.3, p. 183 - 188
[2] Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2.3, p. 183 - 188
  • 9
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  • [ 874-24-8 ]
Reference: [1] Croatica Chemica Acta, 2010, vol. 83, # 3, p. 291 - 298
  • 10
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  • [ 15197-75-8 ]
Reference: [1] Chemische Berichte, 1956, vol. 89, p. 2578,2582
  • 11
  • [ 1121-60-4 ]
  • [ 107-15-3 ]
  • [ 7471-05-8 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 13, p. 2197 - 2199
[2] Tetrahedron, 2007, vol. 63, # 6, p. 1474 - 1480
[3] Australian Journal of Chemistry, 2014, vol. 67, # 10, p. 1516 - 1521
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4704 - 4708
  • 12
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  • [ 7471-05-8 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 3, p. 638 - 643
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 546 - 549
[3] Tetrahedron Letters, 2012, vol. 53, # 23, p. 2876 - 2880
  • 13
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  • [ 17407-44-2 ]
Reference: [1] Chemische Berichte, 1956, vol. 89, p. 2578,2582
  • 14
  • [ 1121-60-4 ]
  • [ 109-04-6 ]
  • [ 35047-29-1 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25 h;
Stage #2: at -78 - 20℃; for 2.5 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
Example 26Preparation of Compounds 174 and 175Step A - Synthesis of Di-(Pyridin-2-yl)-MethanolTo a -78 °C solution of 2-bromoρyridine (3.0 g, 19.0 mmol) in 60 mL THF was added w-BuLi (2.5 M in hexane, 7.6 mL, 19.0 mmol). The resulting reaction was allowed to stir at - 78 °C for about 15 minutes, then 2-pyridine carboxaldehyde (2.17 mL, 22.8 mmol) was added dropwise at -78 °C. The resulting reaction mixture was allowed to stir for 30 minutes at -78 0C, then for 2 hours at room temperature after which time the reaction was quenched with saturated aqueous NH4Cl solution. After diluting the reaction mixture with ethyl acetate, the organic layer was separated and the aqueous layer was back extracted twice with ethyl acetate. The combined organic fractions were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo to provide di-pyridin-2-yl-methanol in 70percent yield as a yellow oil.
Reference: [1] Synlett, 2006, # 16, p. 2553 - 2558
[2] Synlett, 2008, # 9, p. 1418 - 1422
[3] Patent: WO2008/130581, 2008, A1, . Location in patent: Page/Page column 181
[4] Journal of Organic Chemistry, 1993, vol. 58, # 16, p. 4382 - 4388
  • 15
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  • [ 35047-29-1 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1395,1406
  • 16
  • [ 1121-60-4 ]
  • [ 623-73-4 ]
  • [ 26510-52-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 4, p. 875 - 878
[2] Synthesis, 2008, # 11, p. 1685 - 1687
[3] Tetrahedron Letters, 2008, vol. 49, # 32, p. 4788 - 4791
  • 17
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  • [ 26510-52-1 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 31, p. 12616 - 12620
  • 18
  • [ 1121-60-4 ]
  • [ 106-39-8 ]
  • [ 27652-89-7 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With iodine; magnesium In tetrahydrofuran; ethylene dibromide at 20℃; for 2 h;
Stage #2: at 20℃; for 2 h;
To a stirred suspension of magnesium (5.37 g, 223.75 mmol, 3 equiv) in dry THF (60 mL) under argon atmosphere was added iodine (2 crystals), 1,2-dibromo ethane (2 drops). 1-bromo-4-chlorobenzene (25.76 g, 134.39 mmol, 1.8 equiv) was then added dropwise for 1 h at room temperature. The reaction mixture was stirred at room temperature for 1 h. A solution of picolinaldehyde (8 g, 74.68 mmol) in dry THF (19 mL) was added drop wise at room temperature and stirred for 2 h. After completion of reaction, the reaction mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined organic extract was washed with water, brine, dried over sodium sulfate, filteredand concentrated under reduced pressure. Purification using silica gel column chromatography (40percent EtOAc/hexanes as eluent) afforded 12.26 g of (4-chlorophenyl) (pyridin-2-yl) methanol (yield = 75percent). ESI + MS: m/z 220 ([M + Hj).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3044 - 3047
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 219 - 232
[3] Patent: WO2016/100823, 2016, A1, . Location in patent: Page/Page column 115; 116
[4] Patent: US2006/100243, 2006, A1, . Location in patent: Page/Page column 7; sheet 1
  • 19
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  • [ 873-77-8 ]
  • [ 27652-89-7 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 17, p. 3242 - 3247
[2] Patent: US2800485, 1955, ,
  • 20
  • [ 1121-60-4 ]
  • [ 108-90-7 ]
  • [ 27652-89-7 ]
Reference: [1] New Journal of Chemistry, 2013, vol. 37, # 3, p. 563 - 567
  • 21
  • [ 1121-60-4 ]
  • [ 603-50-9 ]
Reference: [1] Patent: DE951987, 1952, ,
[2] Archiv der Pharmazie (Weinheim, Germany), 1955, vol. 288, p. 234,245
[3] Patent: US2764590, 1953, ,
  • 22
  • [ 1121-60-4 ]
  • [ 108-95-2 ]
  • [ 603-50-9 ]
Reference: [1] Patent: US2764590, 1953, ,
  • 23
  • [ 119165-69-4 ]
  • [ 1121-60-4 ]
  • [ 84555-18-0 ]
  • [ 16347-06-1 ]
YieldReaction ConditionsOperation in experiment
23% at 20℃; for 14 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
Reference: [1] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142
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  • [ 3731-51-9 ]
  • [ 16858-01-8 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 6, p. 1804 - 1813
[2] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 467 - 473
[3] Patent: US2012/16127, 2012, A1, . Location in patent: Page/Page column 8
[4] Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2453 - 2458
  • 25
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  • [ 1539-42-0 ]
  • [ 16858-01-8 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 84, p. 12779 - 12782
[2] Dalton Transactions, 2016, vol. 45, # 13, p. 5439 - 5443
  • 26
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  • [ 16858-01-8 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 84, p. 12779 - 12782
  • 27
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  • [ 75-04-7 ]
  • [ 51639-58-8 ]
Reference: [1] Patent: US2009/275588, 2009, A1, . Location in patent: Page/Page column 11
[2] Patent: WO2007/116374, 2007, A1, . Location in patent: Page/Page column 27-28
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  • [ 69716-28-5 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 7, p. 1210 - 1223
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3997 - 4001[3] Angew. Chem., 2016, vol. 128, # 12, p. 4065 - 4069,5
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5290 - 5302
[5] Patent: WO2018/64119, 2018, A1,
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  • [ 131543-46-9 ]
  • [ 18653-75-3 ]
YieldReaction ConditionsOperation in experiment
41% With ammonium hydroxide In ethanol; water at 0 - 20℃; for 6 h; General procedure: An ice-cold solution of the appropriate aldehyde(2-pyridinecarboxyaldehyde (4.668 mmol) or 2-quinolinecarboxyaldehyde(3.181 mmol) in 5 mL ethanol was added to an ice cold solution of 40percent aqueous glyoxal (0.2 mL) in 5 mL ethanol,and then ice-cold concentrated aqueous NH4OH solution(0.15 mL) was added immediately. This solution was stirred at 0 C for 1 h, warmed to room temperature, and stirred for an additional 5 h. The solvent was removed under reduced pressure, andthe resulting solution was extracted several times with diethyl ether. The combined organic extracts were evaporated under reduced pressure and crystalline solids were obtained upon recrystallization with diethyl ether.
34% With ammonium hydroxide In ethanol; water at 0 - 20℃; for 13 h; Inert atmosphere Anhydrous ethanol (25ml), Glyoxal solution (5ml) were stirred in an ice bath, Then, picolinaldehyde (0.54g, 5.02mmol) and concentrated ammonia were added to the mixed solution under nitrogen for 1h. The mixed solution was cooled to room temperature and allowed to stand for 12h, extracted with dichloromethane and washed by water until neutral, and evaporated under reduced pressure to remove the solvent. The product was isolated using silica gel column chromatography with EtAc as the solvent. Recrystallization of the residue from EtOH afforded a brown compound (0.25g, 1.72mmol, 34percent yield).1H NMR (400MHz, DMSO) δ 12.80 (s, 1H), 8.59 (d, J=4.3Hz, 1H), 8.04 (d, J=7.9Hz, 1H), 7.88 (t, J=7.7Hz, 1H), 7.39–7.31 (m, 1H), 7.15 (s, 2H).
32%
Stage #1: at 0℃; for 0.5 h;
Stage #2: With ammonia In ethanol at 0℃; for 4 h;
The overall route for synthesis is depicted by Scheme 1. The ligand was synthesized by some modification of Radziszewski method [20]. In a typical procedure, 5.0g freshly distilled pyridine-2-carboxaldehyde in 5.0ml EtOH at 0°C was added dropwise into 6.75ml glyoxal (dissolved in 5.0ml EtOH) of 0°C and was stirred for 30.0min 19.2ml ammonia at 0°C was added very slowly with constant stirring at 0°C for 4.0h. The mixture was stirred further for 18.0h at room temperature to achieve a deep brown solution. The volume of the content was then reduced to 30percent by rotary evaporator. The remaining content was extracted by diethyl ether (10times×30ml). The ether from the extracted was removed by rotary evaporator and a red oily product was found. It was distilled at 132.0°C under low pressure. Pale yellow needle like crystals were found. Yield 32percent, melting point 136.0°C. 1H NMR (500MHz, CDCl3): 8.46 (d, J=4.8, 1H), 8.09 (d, J=7.6, 1H); 7.71 (td, J=7.6, 3.8 1H); 7.68 (s, 1H), 7.18 (q, 1H), 7.13 (s, 1H). UV/Vis (MeOH): 273 (11,900), 294 (15,600). IR (KBr): ca. 3352w, 1614s, 1595s, 1508m, 1481s, 1458s, 1414s, 1379m, 1307s, 1280m, 1252m, 1171m, 1150s, 1136s, 1107m, 991s, 955s, 901m, 789s, 758s, 737s, 708m, 621s, 657m, 499m, 462m, 430w.
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[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 4, p. 671 - 678
[3] Inorganica Chimica Acta, 2017, vol. 460, p. 63 - 68
[4] Inorganica Chimica Acta, 2019, vol. 484, p. 237 - 244
[5] Journal of Organometallic Chemistry, 2016, vol. 808, p. 42 - 47
[6] Helvetica Chimica Acta, 2005, vol. 88, # 3, p. 487 - 495
[7] Inorganic Chemistry, 2013, vol. 52, # 15, p. 8579 - 8590
[8] Patent: WO2009/11787, 2009, A1, . Location in patent: Page/Page column 102
[9] Patent: US2010/29655, 2010, A1, . Location in patent: Page/Page column 83
[10] Green Chemistry, 2011, vol. 13, # 8, p. 2100 - 2106
[11] RSC Advances, 2013, vol. 3, # 46, p. 24146 - 24153
[12] Journal of Organometallic Chemistry, 2014, vol. 751, p. 430 - 437
[13] Journal of Molecular Structure, 2017, vol. 1145, p. 102 - 111
[14] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 2915 - 2921[15] Zh. Obshch. Khim., 2017, vol. 87, # 12, p. 2915 - 2921,7
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Reference: [1] New Journal of Chemistry, 2018, vol. 42, # 15, p. 12649 - 12665
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  • [ 1336-21-6 ]
  • [ 131543-46-9 ]
  • [ 18653-75-3 ]
Reference: [1] Patent: US2003/96997, 2003, A1,
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Reference: [1] Chemical Communications, 2017, vol. 53, # 3, p. 651 - 654
  • 33
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  • [ 90965-06-3 ]
  • [ 1945-84-2 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In methanol at 20℃; for 1.5 h; Example 104-Methyl-2-[(E)-2-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-vinyl]-thiazole-5-carboxylic acid isopropylamide a) 2-Ethynyl-pyridine; To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e=103.0 [M]+.
71% With potassium carbonate In methanol at 20℃; for 1.5 h; To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (l-diazo-2-oxo-propyl)- phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e = 103.0 [M]+.
Reference: [1] Patent: US2012/115868, 2012, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2012/62623, 2012, A1, . Location in patent: Page/Page column 32
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  • [ 1945-84-2 ]
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[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
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  • [ 31181-90-5 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 19, p. 9805 - 9815
  • 36
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  • [ 94-63-3 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 481,483
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, # 6, p. 1069 - 1078
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  • [ 1122-54-9 ]
  • [ 112881-51-3 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 8, p. 1142 - 1148
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  • [ 619-05-6 ]
  • [ 669070-64-8 ]
YieldReaction ConditionsOperation in experiment
47% With copper(II) acetate monohydrate In ethanol; water at 100℃; for 2 h; To a mixture of 3,4-diaminobenzoic acid (0.6 g, 3.94 mmol, 1 equiv) in EtOH (6 mL) andsolution of cooper acetate monohydrate (0.86 g, 4.33 mmol, 1.1 equiv) in water (10 mL),2-pyridine carboxaldehyde (0.42 mL, 4.33 mmol, 1.1 equiv) was added. The resultingmixture was stirred for 2h at 100°C. Black precipitate was filtered off and dispersed inEtOH (4 mL). Then, Na2SxH2O (1 .7 g) was added and the mixture was stirred for 30mmat 100°C. The obtained solid was filtered off from hot solution and washed with hot wateron the filter. The filtrate was acidified with HOI (pH2) and then the resulted mixture washeating at 80°C till the removing of H25. The cooled mixture was filtered off, concentratedand recrystallized from EtOH. The obtained dihydrochloride product was mixed with an equivalent quantity of KOH in ethanol. The solid was filtered off and the filtrate was concentrated to give (8) (0.447 g, 47percent) as a brown solid
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 13, p. 3289 - 3298
[2] Patent: WO2018/50771, 2018, A1, . Location in patent: Page/Page column 25; 26
  • 39
  • [ 1121-60-4 ]
  • [ 1260765-26-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 6, p. 1410 - 1414
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