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Product Details of [ 1452-63-7 ]

CAS No. :1452-63-7 MDL No. :MFCD00059782
Formula : C6H7N3O Boiling Point : -
Linear Structure Formula :NC5H4CONHNH2 InChI Key :BAQLNPIEFOYKNB-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :255881
Synonyms :
Chemical Name :Picolinohydrazide

Calculated chemistry of [ 1452-63-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.13
TPSA : 68.01 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) : -7.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : -0.83
Log Po/w (WLOGP) : -0.31
Log Po/w (MLOGP) : -0.47
Log Po/w (SILICOS-IT) : -0.27
Consensus Log Po/w : -0.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.48
Solubility : 45.5 mg/ml ; 0.332 mol/l
Class : Very soluble
Log S (Ali) : -0.12
Solubility : 104.0 mg/ml ; 0.762 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.17 mg/ml ; 0.0231 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 1452-63-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1452-63-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1452-63-7 ]
  • Downstream synthetic route of [ 1452-63-7 ]

[ 1452-63-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 2524-52-9 ]
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YieldReaction ConditionsOperation in experiment
93% With hydrazine hydrate In ethanol at 80℃; for 4 h; A mixture of ethyl pyridin-2-carboxylate (90 gm) and hydrazine hydrate (60 gm) in ethanol (400 ml) was stirred at 80° C over a period of 4 h. Solvent was evaporated and to provide a crude mass. The mass was stirred with diethyl ether and the suspension was filtered and the wet cake washed with small quantity of ethanol (50 ml) to provide title compound in 76 gm quantity (93percent) as a white solid.Mass: m/z: 138.0 (M+l)
93% With hydrazine hydrate In ethanol at 80℃; for 4 h; Step-1:
Pyridin-2-carboxylic acid hydrazide
A mixture of ethyl pyridin-2-carboxylate (90 gm) and hydrazine hydrate (60 gm) in ethanol (400 ml) was stirred at 80° C. over a period of 4 h.
Solvent was evaporated and to provide a crude mass.
The mass was stirred with diethyl ether and the suspension was filtered and the wet cake washed with small quantity of ethanol (50 ml) to provide title compound in 76 gm quantity (93percent) as a white solid.
Mass: m/z: 138.0 (M+1)
93% With hydrazine In ethanol at 80℃; for 4 h; Preparation 3: 2- (5-Bromometh yl- 1 ,3,4-thiadiazol-2- yl) -pyridine :Step- 1 : Pyridin-2-carboxylic acid hydrazide:A mixture of ethyl pyridin-2-carboxylate (90 gm) and hydrazine (60 gm) in ethanol (400 ml) was stirred at 80°C over a period of 4 h. Solvent was evaporated under vacuum to provide a crude mass. The crude mass was stirred with diethyl ether and the suspension was filtered and the wet cake washed with small quantity of ethanol (50 ml) to provide title compound in 76 gm quantity (93percent) as a white solid.Mass: m/z: 138 (M+l).
90% With hydrazine hydrate In ethanol at 80℃; for 2 h; To a round-bottom flask was added ethyl picolinate (2.5 mL, 18.52mmol) in ethanol (12 mL) followed by hydrazine monohydrate (1.74 mL, 55.56mmol). The mixture was refluxed for 2h. Ethanol was evaporated after reaction mixture cooled down. The light yellow crude product was washed with diethyl ether (15 mL x 2). Final product as a white solid (2.3 g, 90percent) was collected by vacuum filtration and dried under vacuum. 1H NMR (600 MHz, CDCI3) 9.00 (s, 1H), 8.57 - 8.53 (m, 1H), 8.15 (dd, J = 7.8, 1.2 Hz, 1H), 7.85 (td, J = 7.7, 1.7 Hz, 1H), 7.44 (ddd, J = 7.8, 4.8, 1.2 Hz, 1H), 4.09 (s, 2H); 13C NMR (100MHz, CDCI3) 164.84, 149.17, 148.51, 137.47, 126.61, 122.36
85% With hydrazine In toluene for 18 h; Preparation of pyridine 2-carboxylic acid hydrazine
To 3.0 g (19.8 mmol) of ethyl picolinate are dissolved in 30 ml of toluene, 4.0 ml (79.8 mmol) of anhydrous hydrazine a 100percent are added.
This solution is distillated using a Dean Starck distillator for 18 hour.
The solution is concentrated and dissolved in water and brought to basic pH with ammoniac (20percent).
The precipitate is washed with water and dried.
The relating powder (2.3 g) is pinky R=85percent).
RMN 1H (DMSO-d6, 300 MHz) δ : 4.50 (bs, 2H), 7.54 (m,1H), 7.96 (m,2H), 8.57 (m, 1H), 9.88 (bs, 1H).
MS (ESI+) m/z : 137.9 [M+H].
74% With hydrazine In ethanol for 10 h; Reflux Picolinohydrazide 5 was synthesized by theaddition of a solution containing 50 mmol of hydrazine dissolved in 40 ml ofethanol to 10 mmol of ethyl picolinate 4 and reuxed for 10 h. Then, the volume ofthe solvent was reduced to 10 ml and cooled to room temperature when a whitesolid as the product was precipitated. The crude product was recrystallized inethanol to obtain picolinohydrazide in a yield of 74 percent [22] (Scheme 2).
86% With hydrazine hydrate In ethanol EXAMPLE 58
The synthesis of 2-pyridylhydrazide (58).
Hydrazine hydrate (17.5 ml, 500 mmol) in ethanol (50 ml) was added to a solution of ethyl 2-pyridinecarboxylate (7.53 g, 50.0 mmol) and ethanol (25 ml).
After evaporation and coevaporation with toluene, the product was crystallized from toluene.
The yield was 6.1 g (86percent).
1 H NMR (60 MHz, DMSO-d6): 4.49 (3H, bs); 7.44-7.74 (1H, m); 7.94-8.04 (2H, m); 8.56-8.68 (1H, m)
11.1 g With hydrazine hydrate In ethanol for 3 h; Reflux General procedure: An ethanol (300 ml) suspension of salicylic acid(13.8 g; 0.1 mol) and strongly acidic ion-exchange resin,Amberlyst-15 (5 g) were stirred with refluxing for three days.Insoluble catalyst was separated by filtration, and washed withethanol (3 20 ml). Combined ethanol filtrates were mixed with hydrazine hydrate (20 ml; 20.5 g; 0.4 mol) and refluxed with slowsolvent distillation using the modified Hickman still apparatus(Scheme 3). After 3 h of refluxing, the volume of the reaction mixturewas reduced to about 50 ml and white precipitate started toform. The white suspension was cooled to room temperature andthen left at 5 C for 1 h. Insoluble product was separated by filtration,washed with ice cold ethanol, and dried on air to give pureproduct (13.2 g; 87percent).

Reference: [1] Patent: WO2010/136971, 2010, A1, . Location in patent: Page/Page column 12
[2] Patent: US2012/142710, 2012, A1, . Location in patent: Page/Page column 6
[3] Patent: WO2012/76989, 2012, A1, . Location in patent: Page/Page column 55; 64
[4] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5535 - 5542
[5] Patent: WO2017/106427, 2017, A1, . Location in patent: Page/Page column 37-38
[6] Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1329 - 1334
[7] Patent: EP2338879, 2011, A1, . Location in patent: Page/Page column 11
[8] Photochemistry and Photobiology, 2013, vol. 89, # 5, p. 1020 - 1028
[9] European Journal of Organic Chemistry, 2004, # 16, p. 3422 - 3434
[10] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 8201 - 8215
[11] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2002, vol. 41, # 12, p. 2544 - 2547
[12] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2773 - 2780
[13] European Journal of Medicinal Chemistry, 1990, vol. 25, # 1, p. 75 - 79
[14] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981, vol. 20, # 5, p. 520 - 523
[15] Patent: US5571897, 1996, A,
[16] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7836 - 7841
[17] Patent: WO2011/77098, 2011, A1, . Location in patent: Page/Page column 181-182
[18] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1114 - 1119,6
[19] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297
[20] Organic and Biomolecular Chemistry, 2014, vol. 12, # 27, p. 4975 - 4982
[21] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 54B, # 2, p. 228 - 239
[22] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3397 - 3407
[23] Medicinal Chemistry Research, 2016, vol. 25, # 8, p. 1666 - 1677
[24] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1423 - 1429
[25] ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985
[26] Patent: CN107011255, 2017, A, . Location in patent: Paragraph 0038
[27] Patent: WO2018/160845, 2018, A1, . Location in patent: Paragraph 0220
[28] Patent: CN104892639, 2018, B, . Location in patent: Paragraph 0072; 0073
  • 2
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YieldReaction ConditionsOperation in experiment
100% With hydrazine hydrate In ethanol for 1 h; Reflux To a 500 mL three neck round-bottomed flask equipped with a mechanical stirrer, a reflux condenser, and a nitrogen inlet/outlet was added methyl picolinate (40 g, 0.292 mol), hydrazine hydrate (17.5 g, 0.35 mol) and ethanol (120 mL). The resulting mixture was heated under reflux for 1 h. The solvent was removed under reduced pressure and the resulting residue dried to give the product 40 g (0.292 mol, 100percent) as a white solid. 1H NMR (400 MHz, CDCl3) 8.99 (br s, 1H, —N—H), 8.51 (m, 1H, Ar—H), 8.13 (m, 1H, Ar—H), 7.82 (m, 1H, Ar—H), 7.40 (m, 1H, Ar—H) 4.08 (br s, 2H, —NH2).
Reference: [1] Patent: US2016/244860, 2016, A1, . Location in patent: Paragraph 0158-0159
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 44, p. 8952 - 8965
[3] Journal of the American Chemical Society, 2003, vol. 125, # 49, p. 15128 - 15139
[4] Journal of the American Chemical Society, 2015, vol. 137, # 47, p. 14982 - 14991
[5] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1525 - 1530
[6] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 576 - 588
[7] Journal of Coordination Chemistry, 2011, vol. 64, # 24, p. 4357 - 4372
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5185 - 5189
[9] Journal of Coordination Chemistry, 2012, vol. 65, # 13, p. 2234 - 2246
[10] Heterocyclic Communications, 2013, vol. 19, # 3, p. 171 - 177
[11] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2613 - 2616
[12] Journal of Materials Chemistry B, 2018, vol. 6, # 34, p. 5435 - 5442
  • 3
  • [ 98-98-6 ]
  • [ 1452-63-7 ]
YieldReaction ConditionsOperation in experiment
14.6%
Stage #1: With sulfuric acid In methanol for 12 h; Reflux
Stage #2: With hydrazine hydrate In methanol for 12 h; Reflux
Add to the reaction flask2-picolinic acid (12.31 g, 100 mmol) and methanol (100 ml) were added dropwise 2 mL of concentrated sulfuric acid,Heated to reflux for 12 h. After cooling to room temperature, 20 mL of deionized water was added, and most of the methanol was removed under reduced pressure by a rotary evaporator, followed by extraction with ethyl acetate (100 mL x 5).The resulting organic liquid was dried in anhydrous, filtered, and the solvent was distilled off under reduced pressure. The resulting colorless transparent liquid was dried in a vacuum oven at 50C for 24 hours.To the above-mentioned intermediate was added 100 mL of methanol and 30 mL of 85percent hydrazine hydrate, stirred and refluxed for 12 h.After cooling, the mixture was poured into 200 mL of deionized water and extracted with dichloromethane (100 mL x 5).The resulting organic phase was dried over anhydrous MgSO4 and dried to remove the solid. The resulting filtrate was concentrated, added dropwise to 200 mL of vigorously stirred n-hexane, and stirring was continued for 30 min.The resulting white solid was washed with n-hexane and dried in a vacuum oven at 50 ° C for 24 h to give the product as a white solid, 2-pyridinecarboxylic acid hydrazide (2.0 g, 14.6 mmol) in 14.6percent yield.
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2011, vol. 66, # 12, p. 1202 - 1208
[2] Patent: CN104262404, 2017, B, . Location in patent: Paragraph 0045; 0047
[3] Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 369 - 374
[4] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2002, vol. 41, # 12, p. 2544 - 2547
[5] Australian Journal of Chemistry, 1985, vol. 38, # 10, p. 1491 - 1497
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 1, p. 184 - 187
[7] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5535 - 5542
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5185 - 5189
[9] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1114 - 1119,6
[10] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297
[11] Photochemistry and Photobiology, 2013, vol. 89, # 5, p. 1020 - 1028
[12] Organic and Biomolecular Chemistry, 2014, vol. 12, # 27, p. 4975 - 4982
[13] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 576 - 588
[14] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 54B, # 2, p. 228 - 239
[15] Dalton Transactions, 2015, vol. 44, # 9, p. 4123 - 4132
[16] Russian Journal of General Chemistry, 2015, vol. 85, # 3, p. 746 - 751
[17] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3397 - 3407
[18] New Journal of Chemistry, 2015, vol. 39, # 12, p. 9535 - 9542
[19] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 8201 - 8215
[20] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1423 - 1429
[21] ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985
[22] Patent: CN107011255, 2017, A,
[23] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2773 - 2780
[24] Inorganica Chimica Acta, 2018, vol. 479, p. 148 - 153
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YieldReaction ConditionsOperation in experiment
80.5% With hydrazine hydrate In ethanol for 6 h; Reflux General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 3, p. 746 - 751
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Reference: [1] New Journal of Chemistry, 2015, vol. 39, # 12, p. 9535 - 9542
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Reference: [1] Patent: CN107011255, 2017, A,
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  • [ 29745-44-6 ]
  • [ 1452-63-7 ]
Reference: [1] Patent: CN107011255, 2017, A,
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  • [ 108921-63-7 ]
  • [ 1452-63-7 ]
  • [ 1671-86-9 ]
Reference: [1] Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2.3, p. 183 - 188
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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
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