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[ CAS No. 42823-46-1 ] {[proInfo.proName]}

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Chemical Structure| 42823-46-1
Chemical Structure| 42823-46-1
Structure of 42823-46-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 42823-46-1 ]

CAS No. :42823-46-1 MDL No. :MFCD00040587
Formula : C8H10ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YETFLAUJROGBMC-UHFFFAOYSA-N
M.W : 215.64 Pubchem ID :3084875
Synonyms :

Calculated chemistry of [ 42823-46-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 53.88
TPSA : 101.7 Ų

Pharmacokinetics

GI absorption : Low
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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : -2.59
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 1.23 mg/ml ; 0.0057 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.156 mg/ml ; 0.000725 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.15
Solubility : 15.4 mg/ml ; 0.0716 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 42823-46-1 ]

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 [ 42823-46-1 ]

* 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 [ 42823-46-1 ]
  • Downstream synthetic route of [ 42823-46-1 ]

[ 42823-46-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 420-04-2 ]
  • [ 150-13-0 ]
  • [ 42823-46-1 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With hydrogenchloride In water at 20 - 100℃;
Stage #2: With potassium carbonate In water for 0.5 h;
To a stirred suspension of 4-aminobenzoic acid (50 g, 0.364 mole) in a mixture of concentrated HCl/water (46 mL/283 mL) was added cyanamide (35 g, 0.839 mole) at room temperature. The reaction mixture was heated at 100° C. for 6 hours. The reaction mixture was then allowed stand at room temperature (without stirring) for 16 hours. The precipitated solid was filtered and washed with water (100 mL). The solid was taken in aqueous K2CO3 solution (30 g in 400 mL of water) and stirred for 30 minutes. The solid was filtered, washed with water (2.x.50 mL) and dried under vacuum to provide Int-2A (35 g, 53percent) as white solid. 1H NMR (200 MHz, dmso-d6): δ 8.40-8.21 (bs, 2H), 7.93 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H). Mass (m/z): 180.1 [M++1]. To a stirred suspension of Int-2A (35 g, 195.5 mmol) in methanol (350 mL) was added acetyl chloride (35 mL, 490 mmol) dropwise at 0° C. under inert atmosphere over a period of 20 minutes. The reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material (by thin layer chromatography (TLC)), the reaction mixture was neutralized using solid NaHCO3 at 0° C. Solid (excess NaHCO3) was filtered and filtrate was evaporated under vacuum to get crude compound. The crude compound was washed with EtOAc (100 mL) to afford pure Int-2B (35 g, 92percent) as white solid. 1H NMR (200 MHz, dmso-d6): δ 8.45-8.23 (bs, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 3.83 (s, 3H). Mass (m/z): 194.1 [M++1].
Reference: [1] Patent: US2010/29638, 2010, A1, . Location in patent: Page/Page column 62
[2] European Journal of Medicinal Chemistry, 1996, vol. 31, # 11, p. 895 - 899
  • 2
  • [ 156-62-7 ]
  • [ 150-13-0 ]
  • [ 42823-46-1 ]
YieldReaction ConditionsOperation in experiment
45.8% With hydrogenchloride In water at 80℃; for 3 h; Cooling with ice 1) 100 mL of concentrated hydrochloric acid was added to 250 mL of a three-necked reaction flask and mechanically stirred.2) 10 g of p-aminobenzoic acid and 30 g of lime nitrogen were mixed uniformly.3) The mixture was slowly added to the reaction flask under ice-water bath and stirred into a mixture (insoluble).4) The reaction mixture was allowed to warm to 80 ° C for 3 hours.5) 20 g of lime nitrogen was slowly added to the reaction flask and incubated for 3 hours.6) Check whether the pH of the reaction solution is neutral.7) The reaction solution in the reaction flask was concentrated under reduced pressure at 80 ° C to dryness to give a dark brown solid.8) The solid was subjected to Soxhlet extraction for 3 to 4 hours using 200 mL of methyl tert-butyl ether.9) The methyl tert-butyl ether solution was added to dry anhydrous sodium sulfate.10) A solution of dried methyl tert-butyl ether was passed through the dry HCl gas at room temperature to precipitate a solid.11) The above-mentioned precipitated solid was carefully filtered and the precipitated solid was washed with an appropriate amount of methyl t-butyl ether to obtain a wet product.12) The wet product was poured into a vacuum oven at 45 ° C to give a solution of guanidinobenzoate (7.2 g, 45.8percent).
Reference: [1] Patent: CN106543041, 2017, A, . Location in patent: Paragraph 0023-0037
  • 3
  • [ 1627898-15-0 ]
  • [ 42823-46-1 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3565 - 3569
  • 4
  • [ 150-13-0 ]
  • [ 42823-46-1 ]
Reference: [1] Patent: US5086069, 1992, A,
  • 5
  • [ 623-00-7 ]
  • [ 42823-46-1 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3565 - 3569
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