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Chemical Structure| 4815-24-1
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Product Details of [ 4815-24-1 ]

CAS No. :4815-24-1 MDL No. :MFCD00085051
Formula : C9H13NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :JYSDXODDWAQWJR-UHFFFAOYSA-N
M.W : 199.27 Pubchem ID :78536
Synonyms :

Calculated chemistry of [ 4815-24-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.44
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.74
TPSA : 80.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.24 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (Ali) : -4.14
Solubility : 0.0145 mg/ml ; 0.0000728 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.539 mg/ml ; 0.0027 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.67

Safety of [ 4815-24-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4815-24-1 ]

* 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 [ 4815-24-1 ]
  • Downstream synthetic route of [ 4815-24-1 ]

[ 4815-24-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 77287-34-4 ]
  • [ 4815-24-1 ]
  • [ 18593-44-7 ]
YieldReaction ConditionsOperation in experiment
85% for 6 h; Reflux Take 19.9g (0.1mol) 2- amino-4,5-dimethyl-thiophene-3-carboxylate in 100ml of formamide, heated at reflux for 6 hours, monitored by TLC after completion of the reaction, the reaction solution was cooled to room temperature, was added 100ml of water, stirring was continued for 1 hour, and filtered to give 15.3 g of soil gray solid, 85percent yield, m.p. 274-275 .
49% Reflux General procedure: The different ethyl 2-aminothiophene-3-carboxylate (5a-g) (1 eq.) and formamide (3.2mL/mmol eq.) were refluxed for 8 h. The reaction mixture was then cooled in an ice-bath and added of cold water. The precipitate formed was collected by filtration, washed thoroughly with cold water and purified by crystallisation from EtOH/H2O unless otherwise stated.
Reference: [1] Molecules, 2010, vol. 15, # 6, p. 3932 - 3957
[2] Patent: CN105218557, 2016, A, . Location in patent: Paragraph 0214; 0215; 0216
[3] Journal of Structural Chemistry, 2001, vol. 42, # 6, p. 995 - 1001
[4] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 31 - 47
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 870 - 876
[6] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 148 - 160
[7] Chemical Biology and Drug Design, 2017, vol. 90, # 6, p. 1115 - 1121
  • 2
  • [ 3473-63-0 ]
  • [ 4815-24-1 ]
  • [ 18593-44-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5992 - 5994
  • 3
  • [ 74-90-8 ]
  • [ 4815-24-1 ]
  • [ 18593-44-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 3, p. 496 - 500
  • 4
  • [ 4815-24-1 ]
  • [ 18593-44-7 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 432 - 433
  • 5
  • [ 105-56-6 ]
  • [ 78-93-3 ]
  • [ 4815-24-1 ]
YieldReaction ConditionsOperation in experiment
75% With sulfur; diethylamine In ethanol at 20℃; for 8 h; Synthesis of ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate. Into a mixture of butan-2-one (20 g, 0.28 mol, 1.0 eq), ethyl 2-cyanoacetate (31.4 g, 0.28 mol, 1.0 eq), and sulphur (8.9 g, 0.28 mol, 1.0 eq) in 100 mL of ethanol was added diethyl amine (21 g, 0.28 mol, 1.0 eq). The mixture was stirred for 8 h at room temperature. The reaction mixture was diluted with water and the precipitate was collected by filtration and recrystallized from ethanol to afford ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate as yellow solid (41 g, 75percent).
72% at 60℃; for 2 h; Ionic liquid; Green chemistry General procedure: For the synthesis of 4,5-alkyl-2-aminothiophenes (2a–2j), the general procedures are the same as those of compound 2i. A mixture of N-benzyl-4-piperidone (1i, 380 mg, 2 mmol), malononitrile (132 mg, 2 mmol), sulfur (64 mg, 2 mmol), and basic ionic liquid (bmIm)OH (380 mg, 2.4 equiv.) was heated to 60°C for 2 h. The reaction mixture was cooled to room temperature and washed with diethyl ether or ethyl acetate (340 mL),and the organic layers were concentrated under vacuum to obtain an oily crude product. The crude product was dissolved in ether/hexane (3:1, 50 mL) mixture, insoluble material was decanted, and the organic layer was concentrated to 1/4 of the volume and kept in a refrigerator. The precipitate that formed was filtered and dried.
61% With sulfur; diethylamine In ethanol at 20℃; for 1.25 h; General procedure: Diethylamine (0.1mol) was added dropwise for 30min to a suspension of the appropriate ketone (0.1mol), ethyl cyanacetate 0.1mol (11ml) and 3.2g sulfur in 30ml ethanol and the reaction mixture was stirred at room temperature for about 75min. When the synthesis was completed the mixture was cooled. The obtained 2-aminothiophene crystalized in the form of yellow powder. The precipitate was filtrated, washed with water and recrystallized from ethanol to give the 2-aminothiophene derivatives [27]. 6.1.1
Ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate (1a)
Yield: 61percent; Mp. 97-100 °C
[1]
; IR (KBr): 3300 cm-1 (NH), 2920 cm-1 (CH3), 2860 cm-1 (CH3), 1640 cm-1 (C=O), 1160 cm-1 (C-O); Analysis: Calc. for C9H13NO2S: C, 54.25; H, 6.58; N, 7.03; O, 16.06; S, 16.09; Found: C, 54.30; H, 6.55; N, 7.08; O, 16.10; S, 16.10.
57% With octasulfur; bovine serum albumin In N,N-dimethyl-formamide at 50℃; for 12 h; General procedure: A mixture of 1 (1 mmol), 2 (1 mmol), elemental sulfur (1 mmol)and BSA (20 mg) was added to 1 mL of DMF. The reaction was incubatedat 50 C and 200 rpm. After the required time, the BSA wasfiltered off to terminate the reaction. For the products with highyields, the solid crude products precipitated in water, and then followedby filtration and drying. For the products with low yields,the crude residues were purified by flash column chromatographyon silica gel using petroleum/ethyl acetate.
47% With sulfur; triethylamine In ethanol for 24 h; Reflux General procedure: To a mixture of ketone (1 eq.), ethyl cyanoacetate (4) (1 eq.), and elemental sulfur (1 eq.) in absolute ethanol (1.7 mL/mmol eq.) was added triethylamine (1.5 eq.), and the mixture was refluxed for 24 h. The reaction mixture was then concentrated and the residue was partitioned between water (10 mL/mmol eq.)and ethyl acetate (10 mL/mmol eq.). The organic layer was separated, dried over MgSO4, and concentrated, and the crude product was purified by crystallization from EtOH/H2O unless otherwise stated.#10;

Reference: [1] Synthetic Communications, 2012, vol. 42, # 16, p. 2367 - 2374
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2091 - 2092
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 24, p. 4233 - 4242
[4] Journal of Sulfur Chemistry, 2014, vol. 35, # 3, p. 261 - 269
[5] Journal of Heterocyclic Chemistry, 2014, vol. 51, # SUPPL. 1, p. E216-E221
[6] Patent: WO2012/97013, 2012, A1, . Location in patent: Page/Page column 120
[7] Synthetic Communications, 2015, vol. 45, # 1, p. 119 - 126
[8] Synthetic Communications, 2004, vol. 34, # 20, p. 3801 - 3806
[9] Turkish Journal of Chemistry, 2011, vol. 35, # 6, p. 915 - 924
[10] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 69 - 79
[11] Synthetic Communications, 2007, vol. 37, # 23, p. 4273 - 4279
[12] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3171 - 3172
[13] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 29 - 35
[14] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 1014 - 1022
[15] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 31 - 47
[16] Synthetic Communications, 2013, vol. 43, # 13, p. 1859 - 1864
[17] Pharmazie, 1987, vol. 42, # 3, p. 160 - 161
[18] Journal of Chemical Research, 2008, # 6, p. 334 - 339
[19] European Journal of Medicinal Chemistry, 2010, vol. 45, # 5, p. 1739 - 1745
[20] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 870 - 876
[21] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5992 - 5994
[22] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 148 - 160
[23] Chemical Biology and Drug Design, 2017, vol. 90, # 6, p. 1115 - 1121
  • 6
  • [ 4815-24-1 ]
  • [ 55502-96-0 ]
Reference: [1] Patent: US3951989, 1976, A,
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