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[ CAS No. 23628-31-1 ] {[proInfo.proName]}

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Chemical Structure| 23628-31-1
Chemical Structure| 23628-31-1
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Product Details of [ 23628-31-1 ]

CAS No. :23628-31-1 MDL No. :MFCD00233711
Formula : C6H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NMCKJFCJIHCHIS-UHFFFAOYSA-N
M.W : 138.12 Pubchem ID :351652
Synonyms :

Calculated chemistry of [ 23628-31-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.6
TPSA : 76.21 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) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.52
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : -1.31
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : -0.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.19
Solubility : 8.83 mg/ml ; 0.064 mol/l
Class : Very soluble
Log S (Ali) : -1.35
Solubility : 6.19 mg/ml ; 0.0448 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.01
Solubility : 13.5 mg/ml ; 0.0977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 23628-31-1 ]

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

Application In Synthesis of [ 23628-31-1 ]

* 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 [ 23628-31-1 ]
  • Downstream synthetic route of [ 23628-31-1 ]

[ 23628-31-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 26893-72-1 ]
  • [ 23628-31-1 ]
Reference: [1] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736
[2] Patent: US6689754, 2004, B1,
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 14, p. 2238 - 2241
[4] Supramolecular Chemistry, 2010, vol. 22, # 9, p. 483 - 490
[5] Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596
[6] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
[7] Patent: EP2017275, 2009, A1, . Location in patent: Page/Page column 153; 154
  • 2
  • [ 5327-33-3 ]
  • [ 23628-31-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 14, p. 2238 - 2241
[2] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736
[3] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
[4] Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596
  • 3
  • [ 1824-81-3 ]
  • [ 23628-31-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 11, p. 2741 - 2748
[2] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736
  • 4
  • [ 4684-94-0 ]
  • [ 23628-31-1 ]
Reference: [1] Patent: CH227124, 1941, ,
  • 5
  • [ 21190-87-4 ]
  • [ 23628-31-1 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 10, p. 2343 - 2352
  • 6
  • [ 13538-41-5 ]
  • [ 23628-31-1 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 10, p. 2343 - 2352
  • 7
  • [ 23628-31-1 ]
  • [ 64-17-5 ]
  • [ 69142-64-9 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: at 0℃; Reflux
Stage #2: With sodium carbonate In water
To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 91 (5.5 g, 76percent).
76% at 0℃; for 12 h; Reflux Example 6. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(2- (trifluoromethyl)phenyl)benzo[d]oxazole-7-carboxamide (Compound 125) : Step 1) Preparation of ethyl 6-aminopicolinate (20): 19 20To a solution of 2-amino-6-pyridinecarboxyric acid (19; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 20 (5.5 g, 76percent).
76%
Stage #1: at 0℃; Reflux
Stage #2: With sodium carbonate In water
Step 1. Preparation of ethyl 6-aminopicolinate (78):To a solution of 2-amino-6-pyridinecarboxylic acid 77 (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford 78 (5.5 g, 76 percent yield).
76%
Stage #1: at 0℃; for 12 h; Reflux
Stage #2: With sodium carbonate In water
Example 3. Preparation of 2-(4-fluoro-2-(trifluoromethyl)phenyl)-N-(6- (morpholinomethyl) pyridine-2-yl)-3H-imidazo[4,5-b]pyridine-7-carboxamide (Compound 110):; Step 1) Synthesis of ethyl 6-aminopicolinate (10): 9 10To a solution of 2-amino-6-pyridinecarboxylic acid (9; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101.0 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 10 (5.5 g, 76percent). MS (ESI) calcd for C8Hi0N2O2: 166.2; found: 167 [M+H].
76%
Stage #1: at 0℃; Reflux
Stage #2: With sodium carbonate In water
To a solution of 2-amino-6-pyridinecarboxylic acid (64; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 00C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 65 (5.5 g, 76percent). MS (ESI) calcd for C8Hi0N2O2: 166.2; found: 167 [M+H].
76%
Stage #1: at 0℃; for 12 h; Reflux
Stage #2: With sodium carbonate In water
Step 1. Preparation of ethyl 6-aminopicolinate:To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 °C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2C03 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76percent).
76% at 0℃; for 12 h; Reflux To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 °C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temp for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76 percent yield)
76% at 0℃; for 12 h; Reflux Step 1)
Preparation of ethyl 6-aminopicolinate:
To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 °C.
The resulting reaction mixture was stirred under reflux for 12 h.
Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure.
Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9.
The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue.
The mixture was stirred vigorously at room temperature for 30 min and then filtered.
The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76percent).
76% at 0℃; for 12 h; Reflux To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 °C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temp for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76 percent yield).
76%
Stage #1: at 0℃; Reflux
Example 11. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(3- (trifluoromethyl)phenyl) imidazo[l,2-a]pyridine-8-carboxamide (Compound 159): Step 1) Preparation of ethyl 6-aminopicolinate (43): 42 43 To a solution of 2-amino-6-pyridinecarboxylic acid (42; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 00C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 43 (5.5 g, 76percent).

Reference: [1] Patent: WO2010/3048, 2010, A1, . Location in patent: Page/Page column 107
[2] Patent: WO2010/19606, 2010, A1, . Location in patent: Page/Page column 81-82
[3] Patent: WO2010/37127, 2010, A1, . Location in patent: Page/Page column 109
[4] Patent: WO2010/88574, 2010, A1, . Location in patent: Page/Page column 127-128
[5] Patent: WO2010/101949, 2010, A1, . Location in patent: Page/Page column 132; 133
[6] Patent: WO2011/116176, 2011, A1, . Location in patent: Page/Page column 78
[7] Patent: WO2013/59587, 2013, A1, . Location in patent: Page/Page column 195; 196
[8] Patent: EP2273992, 2016, B1, . Location in patent: Paragraph 0356; 0357
[9] Patent: EP2768509, 2017, B1, . Location in patent: Paragraph 0774; 0775
[10] Patent: WO2009/146358, 2009, A1, . Location in patent: Page/Page column 78
[11] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736
[12] Patent: EP2017275, 2009, A1, . Location in patent: Page/Page column 153; 154
  • 8
  • [ 23628-31-1 ]
  • [ 69142-64-9 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 43, p. 8419 - 8427
[2] Synthetic Communications, 2013, vol. 43, # 8, p. 1173 - 1180
  • 9
  • [ 23628-31-1 ]
  • [ 79651-61-9 ]
  • [ 79651-64-2 ]
Reference: [1] Patent: US4362728, 1982, A,
  • 10
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
  • 11
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
  • 12
  • [ 23628-31-1 ]
  • [ 332884-35-2 ]
Reference: [1] Patent: WO2014/186313, 2014, A1,
[2] Patent: US2015/152108, 2015, A1,
[3] Patent: EP2768509, 2017, B1,
[4] Patent: WO2013/59587, 2013, A1,
  • 13
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
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