Home Cart 0 Sign in  
X

[ CAS No. 17288-35-6 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 17288-35-6
Chemical Structure| 17288-35-6
Chemical Structure| 17288-35-6
Structure of 17288-35-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Quality Control of [ 17288-35-6 ]

Related Doc. of [ 17288-35-6 ]

SDS
Alternatived Products of [ 17288-35-6 ]

Product Details of [ 17288-35-6 ]

CAS No. :17288-35-6 MDL No. :MFCD09955613
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :162.15 g/mol Pubchem ID :22612670
Synonyms :

Calculated chemistry of of [ 17288-35-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.05
TPSA : 65.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.74
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 0.18
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 0.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.92
Solubility : 1.95 mg/ml ; 0.012 mol/l
Class : Very soluble
Log S (Ali) : -1.9
Solubility : 2.03 mg/ml ; 0.0125 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.863 mg/ml ; 0.00532 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 17288-35-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17288-35-6 ]

* 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 [ 17288-35-6 ]
  • Downstream synthetic route of [ 17288-35-6 ]

[ 17288-35-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 17288-32-3 ]
  • [ 17288-35-6 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium hydroxide In ethanol; water for 16 h;
Stage #2: Acidic conditions
3-Amino-2-chloro-pyridine 4f (150 mg, 1.17 mmol), ethyl pyruvate 8 (0.25 ml, 2.00 mmol), pyridinium p-toluenesulfonate, (73 mg, 0.29 mmol) and tetraethoxy-silane (0.26 ml, 1.18 mmol) were suspended in 0.4 ml pyridine and stirred for 24 h at 20 °C. Afterwards Pd[P(C6H6)3]4 (70 mg, 0.06 mmol) and N,N-dicyclohexylmethylamine (0.35 ml, 2.06 mmol) were added and the reaction mixture was heated in a microwave oven to 160 °C for 20 min. The reaction mixture is diluted with 100 ml dichloromethan and extracted two times with 50 ml of a half saturated aqueous sodium hydrogencarbonat solution. The organic layer was dried with sodium sulfate, the solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P3, yielding 190 mg (1.00 mmol) of 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester. The ester was dissolved in 17 ml ethanol and 5 ml water. To this solution lithium hydroxide (120 mg, 5.00 mmol) was added. After 16 h the pH value of the reaction mixture was adjusted to pH 4 and the solvent is evaporated in vacuum. The crude product was purified using an acid ion exchanger (Strata-X-C, Phenomenex), yielding of 155 mg (82percent) of the title compound. Purity by method A1: >95percent; MS (ESI) m/z 163 (M + H)+; 1H NMR (DMSO) δ (ppm) 13.34 (br, 1H), 8.77 (d, J = 5.3 Hz, 1H), 8.53 (d, J = 8.3 Hz, 1H), 7.73 (dd, J = 5.4 Hz, J = 8.3 Hz, 1H), 7.33 (br, 1H); 13C NMR (500 MHz, DMSO) δ (ppm) 161.4 (s), 138.0 (s), 136.1 (s), 135.8 (s), 132.7 (s), 128.6 (s), 119.6 (s), 101.2 (s).
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 660 - 668
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 42-43
  • 2
  • [ 39856-58-1 ]
  • [ 127-17-3 ]
  • [ 17288-35-6 ]
Reference: [1] Patent: EP1479680, 2004, A1, . Location in patent: Page 48
  • 3
  • [ 17288-32-3 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 4
  • [ 18699-87-1 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Patent: WO2004/104001, 2004, A2,
  • 5
  • [ 5470-18-8 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Patent: WO2004/104001, 2004, A2,
  • 6
  • [ 17288-30-1 ]
  • [ 17288-35-6 ]
Reference: [1] Patent: WO2004/104001, 2004, A2,
  • 7
  • [ 23596-34-1 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 8
  • [ 64362-41-0 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 9
  • [ 18699-87-1 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 10
  • [ 5470-18-8 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 11
  • [ 23596-34-1 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 12
  • [ 64362-41-0 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 13
  • [ 67-56-1 ]
  • [ 17288-32-3 ]
  • [ 394223-19-9 ]
  • [ 853685-35-5 ]
  • [ 17288-35-6 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
  • 14
  • [ 6298-19-7 ]
  • [ 17288-35-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 660 - 668
  • 15
  • [ 64-17-5 ]
  • [ 17288-35-6 ]
  • [ 17288-32-3 ]
Reference: [1] Patent: WO2018/119395, 2018, A1, . Location in patent: Page/Page column 134; 135
[2] Patent: WO2018/195075, 2018, A1, . Location in patent: Page/Page column 55; 100; 101
Historical Records

Related Functional Groups of
[ 17288-35-6 ]

Carboxylic Acids

Chemical Structure| 920979-05-1

[ 920979-05-1 ]

5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid

Similarity: 0.82

Chemical Structure| 1190319-18-6

[ 1190319-18-6 ]

1H-Pyrrolo[3,2-b]pyridine-7-carboxylic acid

Similarity: 0.81

Chemical Structure| 112766-32-2

[ 112766-32-2 ]

1H-Pyrrolo[3,2-b]pyridine-6-carboxylic acid

Similarity: 0.78

Chemical Structure| 130473-27-7

[ 130473-27-7 ]

1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid

Similarity: 0.75

Chemical Structure| 800401-71-2

[ 800401-71-2 ]

5-Bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Similarity: 0.74

Related Parent Nucleus of
[ 17288-35-6 ]

Other Aromatic Heterocycles

Chemical Structure| 17288-32-3

[ 17288-32-3 ]

Ethyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Similarity: 0.90

Chemical Structure| 872355-63-0

[ 872355-63-0 ]

Methyl 1H-pyrrolo[3,2-b]pyridine-5-carboxylate

Similarity: 0.84

Chemical Structure| 920979-05-1

[ 920979-05-1 ]

5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid

Similarity: 0.82

Chemical Structure| 1190319-18-6

[ 1190319-18-6 ]

1H-Pyrrolo[3,2-b]pyridine-7-carboxylic acid

Similarity: 0.81

Chemical Structure| 112766-32-2

[ 112766-32-2 ]

1H-Pyrrolo[3,2-b]pyridine-6-carboxylic acid

Similarity: 0.78