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Chemistry
Organic Building Blocks
Pyridines
triamine
Pyridine-3,4,5-triamine
Chemistry
Material Science
Organic Building Blocks
Heterocyclic Building Blocks COFs Linkers
Pyridines
Amines Amine COFs Linkers
triamine
pyridin-3-amine

[ CAS No. 618439-82-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 618439-82-0
Chemical Structure| 618439-82-0
Structure of 618439-82-0 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 618439-82-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 618439-82-0 ]

Product Details of [ 618439-82-0 ]

CAS No. :618439-82-0 MDL No. :MFCD09753793
Formula : C5H8N4 Boiling Point : -
Linear Structure Formula :- InChI Key :UIQHHOMREHEPJX-UHFFFAOYSA-N
M.W : 124.14 Pubchem ID :419566
Synonyms :

Calculated chemistry of [ 618439-82-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 3.0
Molar Refractivity : 37.45
TPSA : 90.95 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.36
Log Po/w (XLOGP3) : -1.19
Log Po/w (WLOGP) : -0.15
Log Po/w (MLOGP) : -1.44
Log Po/w (SILICOS-IT) : -0.73
Consensus Log Po/w : -0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.35
Solubility : 55.0 mg/ml ; 0.443 mol/l
Class : Very soluble
Log S (Ali) : -0.23
Solubility : 73.7 mg/ml ; 0.594 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.9
Solubility : 15.5 mg/ml ; 0.125 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 618439-82-0 ]

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 [ 618439-82-0 ]

* 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 [ 618439-82-0 ]

[ 618439-82-0 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 618439-82-0 ]
  • [ 131543-46-9 ]
  • [ 120208-34-6 ]
YieldReaction ConditionsOperation in experiment
80% In ethanol; water at 70℃; for 4h;
Reference： [1]Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo [Organic Letters, 2007, vol. 9, # 3, p. 401 - 404]
[2]Israel; Day [Journal of Organic Chemistry, 1959, vol. 24, p. 1455,1459]
  • 2
  • [ 618439-82-0 ]
  • [ 431-03-8 ]
  • [ 109868-80-6 ]
YieldReaction ConditionsOperation in experiment
With water
Reference： [1]Israel; Day [Journal of Organic Chemistry, 1959, vol. 24, p. 1455,1459]
  • 3
  • [ 4318-68-7 ]
  • [ 618439-82-0 ]
YieldReaction ConditionsOperation in experiment
With ethanol; platinum Hydrogenation;
Reference： [1]Graboyes; Day [Journal of the American Chemical Society, 1957, vol. 79, p. 6421,6423,6424]
  • 4
  • [ 31793-29-0 ]
  • [ 618439-82-0 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In ethanol for 18h; 2 Example 2 Pyridine-3,4,5-triamine (3). 3,5-Dinitro-pyridin-4-ylamine 2 (5.00 g, 27 mmol) was suspended in EtOH (80 ml). The flask was evacuated and then purged with a nitrogen atmosphere. To this flask, Pt/C (500 mg of 10%) was added. The flask was re-evacuated, and then placed under a hydrogen atmosphere (40 psi) on a Parr hydrogenator. It was allowed to shake for 18 hours, and was judged complete by TLC. The platinum catalyst was removed by CELITE filtration, and the solvent was removed by evaporation under a reduced atmosphere to yield the title product 3, a brown solid (3.24 g (97%), 27 mmol). 1H NMR (20): δ 7.51 (s, 2H). MS (ESI-POS): [M+H]+=125.
92% With 1% Pd/C; hydrogen In ethanol
70% With ethanol; tin(ll) chloride for 6h; Reflux;
With ethanol; nickel Hydrogenation;
Multi-step reaction with 2 steps 1: aqueous ammonium polysulfide 2: platinum; ethanol / Hydrogenation

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/189616, 2006, A1 Location in patent: Page/Page column 13; 19
[2]Vera, Matthew D.; Lundquist IV, Joseph T.; Chengalvala, Murty V.; Cottom, Joshua E.; Feingold, Irene B.; Garrick, Lloyd M.; Green, Daniel M.; Hauze, Diane B.; Mann, Charles W.; Mehlmann, John F.; Rogers, John F.; Shanno, Linda; Wrobel, Jay E.; Pelletier, Jeffrey C. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2512 - 2515]
[3]Location in patent: experimental part Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
[4]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - DE670920, 1937, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 360][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 360]
[5]Graboyes; Day [Journal of the American Chemical Society, 1957, vol. 79, p. 6421,6423,6424]
  • 5
  • [ 618439-82-0 ]
  • [ 150-13-0 ]
  • 2-(4-Amino-phenyl)-3H-imidazo[4,5-c]pyridin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With PPA
Reference： [1]Tret'yakova, A. V.; Rudaya, L. I.; El'tsov, A. V. [Journal of general chemistry of the USSR, 1984, vol. 54, # 11, p. 2338 - 2340][Zhurnal Obshchei Khimii, 1984, vol. 54, # 11, p. 2617 - 2620]
  • 6
  • [ 618439-82-0 ]
  • [ 65-49-6 ]
  • 5-Amino-2-(7-amino-3H-imidazo[4,5-c]pyridin-2-yl)-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With PPA
Reference： [1]Tret'yakova, A. V.; Rudaya, L. I.; El'tsov, A. V. [Journal of general chemistry of the USSR, 1984, vol. 54, # 11, p. 2338 - 2340][Zhurnal Obshchei Khimii, 1984, vol. 54, # 11, p. 2617 - 2620]
YieldReaction ConditionsOperation in experiment
3,4-Diamino-5-nitropyridin, 5percentig. Pd/C (Hydrier.);
Representative compounds of the present invention are: ... 4-methyl-2,3,6-pyridinetriamine; 4-(methylthio)-2,3,6-pyridinetriamine; 4-ethoxy-2,3,6-pyridinetriamine; 2,3,6-pyridinetriamine; 3,4,5-pyridinetriamine; 4-methoxy-2,3-pyridinediamine; 5-methoxy-2,3-pyridinediamine; 6-methoxy-2,3-pyridinediamine;
  • 8
  • [ 618439-82-0 ]
  • [ 927385-20-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / H2O; ethanol / 4 h / 70 °C 2: 65 percent / triethylamine / CH2Cl2 / 5 h
Reference： [1]Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo [Organic Letters, 2007, vol. 9, # 3, p. 401 - 404]
  • 9
  • [ 618439-82-0 ]
  • N-(2-chloroethyl)-N-(1,2,3,4-tetrahydro-pyrido[3,4-b]pyrazin-8-yl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / H2O; ethanol / 4 h / 70 °C 2: 65 percent / triethylamine / CH2Cl2 / 5 h 3: 52 percent / sodium borohydride; trifluoroacetic acid / tetrahydrofuran / 7 h
Reference： [1]Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo [Organic Letters, 2007, vol. 9, # 3, p. 401 - 404]
  • 10
  • [ 618439-82-0 ]
  • [ 927385-22-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / H2O; ethanol / 4 h / 70 °C 2: 65 percent / triethylamine / CH2Cl2 / 5 h 3: 52 percent / sodium borohydride; trifluoroacetic acid / tetrahydrofuran / 7 h 4: 57 percent / sodium methoxide / methanol / 14 h / Heating
Reference： [1]Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo [Organic Letters, 2007, vol. 9, # 3, p. 401 - 404]
  • 11
  • [ 618439-82-0 ]
  • 1,6-diethyl-2,3,5,6-tetrahydro-1H,4H-1,3a,6,8-tetraaza-phenalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / H2O; ethanol / 4 h / 70 °C 2: 65 percent / triethylamine / CH2Cl2 / 5 h 3: 52 percent / sodium borohydride; trifluoroacetic acid / tetrahydrofuran / 7 h 4: 57 percent / sodium methoxide / methanol / 14 h / Heating 5: 62 percent / sodium cyanoborohydride / methanol; H2O / 5 h / 20 °C
Reference： [1]Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo [Organic Letters, 2007, vol. 9, # 3, p. 401 - 404]
  • 12
  • [ 504-24-5 ]
  • [ 618439-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: aqueous ammonium polysulfide 3: platinum; ethanol / Hydrogenation
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 10 - 85 °C 2: ethanol; tin(ll) chloride / 6 h / Reflux
Reference： [1]Graboyes; Day [Journal of the American Chemical Society, 1957, vol. 79, p. 6421,6423,6424]
[2]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 13
  • [ 618439-82-0 ]
  • [ 939-97-9 ]
  • [ 906461-83-4 ]
YieldReaction ConditionsOperation in experiment
37% In isopropyl alcohol for 48h; Heating / reflux; 4 Example 4 2-(4-tert-Butyl-phenyl)-1H-imidazo[4,5-c]pyridin-7-ylamine (4). Pyridine-3,4,5-triamine 3 (100 mg, 0.81 mmol) was dissolved in isopropanol (4 ml) with Pd/C (20 mg of 10% powder). 4-t-butyl benzaldehyde (150 mg, 0.92 mmol) was added, and this mixture was refluxed for 48 hours. The reaction mixture was filtered through CELITE to remove the palladium, and the crude was purified by HPLC (Method E) to yield the title compound 4 (81 mg (37%), 0.3 mmol). 1H NMR (DMSO-d6): δ 8.64 (bs, 1H), 8.18 (d, J=8.6 Hz, 2H), 7.75 (s,1H), 7.69 (d, J=8.6 Hz, 2H), 6.30-6.61 (bs, 2H), 1.35 (s, 9H). MS (ESI-POS): [M+H]+=266.
24% With 1% Pd/C
Reference： [1]Current Patent Assignee: PFIZER INC - US2006/189616, 2006, A1 Location in patent: Page/Page column 13; 19
[2]Vera, Matthew D.; Lundquist IV, Joseph T.; Chengalvala, Murty V.; Cottom, Joshua E.; Feingold, Irene B.; Garrick, Lloyd M.; Green, Daniel M.; Hauze, Diane B.; Mann, Charles W.; Mehlmann, John F.; Rogers, John F.; Shanno, Linda; Wrobel, Jay E.; Pelletier, Jeffrey C. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2512 - 2515]
  • 14
  • [ 618439-82-0 ]
  • [ 1305317-16-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2: pyridine / 24 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 15
  • [ 618439-82-0 ]
  • [ 1305317-17-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 7 h / 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 16
  • [ 618439-82-0 ]
  • [ 1305317-18-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 8 h / 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 17
  • [ 618439-82-0 ]
  • [ 1305317-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 8 h / 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 18
  • [ 618439-82-0 ]
  • [ 1305317-20-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 5 h / 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 19
  • [ 618439-82-0 ]
  • [ 1305317-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 6 h / 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 20
  • [ 618439-82-0 ]
  • [ 1305317-24-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2: pyridine / 24 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 21
  • [ 618439-82-0 ]
  • [ 1305317-25-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / Reflux 2: pyridine / 24 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 22
  • [ 618439-82-0 ]
  • [ 1305317-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 20 °C
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 23
  • [ 618439-82-0 ]
  • [ 1305317-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2: caesium carbonate / acetonitrile / 19 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 24
  • [ 618439-82-0 ]
  • [ 1305317-27-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / Reflux 2: caesium carbonate / acetonitrile / 24 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 25
  • [ 618439-82-0 ]
  • [ 1305317-28-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / Reflux 2: caesium carbonate / acetonitrile / 24 h / Reflux
Reference： [1]Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 26
  • [ 618439-82-0 ]
  • [ 1226-42-2 ]
  • [ 1305317-11-6 ]
YieldReaction ConditionsOperation in experiment
31% With sodium hydrogencarbonate In 1,4-dioxane; water Reflux;
Reference： [1]Location in patent: experimental part Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 27
  • [ 618439-82-0 ]
  • [ 134-81-6 ]
  • [ 788821-74-9 ]
YieldReaction ConditionsOperation in experiment
23% With sodium hydrogencarbonate In 1,4-dioxane; water for 6h; Reflux;
Reference： [1]Location in patent: experimental part Antoine, Maud; Czech, Michael; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Marchand, Pascal [Synthesis, 2011, # 5, p. 794 - 806]
  • 28
  • [ 618439-82-0 ]
  • [ 1075-06-5 ]
  • [ 1361298-35-2 ]
YieldReaction ConditionsOperation in experiment
54% With sodium hydrogencarbonate In 1,4-dioxane for 6h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Antoine, Maud; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Czech, Michael; Seipelt, Irene; Marchand, Pascal [Synthesis, 2012, vol. 44, # 1, p. 69 - 82]
  • 29
  • [ 618439-82-0 ]
  • 2,2-dihydroxy-1-(4-hydroxyphenyl)ethan-1-one [ No CAS ]
  • [ 1361298-39-6 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydrogencarbonate In 1,4-dioxane for 6h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Antoine, Maud; Gerlach, Matthias; Guenther, Eckhard; Schuster, Tilmann; Czech, Michael; Seipelt, Irene; Marchand, Pascal [Synthesis, 2012, vol. 44, # 1, p. 69 - 82]

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