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[ CAS No. 18593-44-7 ]

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Chemical Structure| 18593-44-7
Chemical Structure| 18593-44-7
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Product Details of [ 18593-44-7 ]

CAS No. :18593-44-7 MDL No. :MFCD00463622
Formula : C8H8N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :QAFMGDDXMIKGEY-UHFFFAOYSA-N
M.W :180.23 Pubchem ID :403053
Synonyms :

Calculated chemistry of [ 18593-44-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.17
TPSA : 73.99 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 3.66
Consensus Log Po/w : 1.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.647 mg/ml ; 0.00359 mol/l
Class : Soluble
Log S (Ali) : -2.64
Solubility : 0.412 mg/ml ; 0.00229 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.095 mg/ml ; 0.000527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.34

Safety of [ 18593-44-7 ]

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 [ 18593-44-7 ]

* 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 [ 18593-44-7 ]
  • Downstream synthetic route of [ 18593-44-7 ]

[ 18593-44-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 51486-04-5 ]
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YieldReaction ConditionsOperation in experiment
85% at 130℃; for 0.166667 h; Microwave irradiation General procedure: A mixture of 1a,b ( 1 mmol) and formamide( 5-6 mmol) in ( 1 mmol) acetic acid, was irradiationin the microwave oven for 10 min. at (300 W) 130 °C.The reaction mixture was cooled and poured intoiced-cold water, filtered, washed and recrystallized from ethanol. . 5,6-Dimethyl-3H-thieno[2,3-d]pyrimidin-4-one (4a) M.p. 180-183 °C; IR(cm-1): 3320, 1670; 1H-NMR(DMSO-d6) 1.7(s, 3H, CH3), 2.0(s, 3H, CH3),7.80 (1H, s, pyrimidine-H), 10.00 (br. s, 1H, NH);MS: m/z (percent), 180[M+] (95) (C8H8N2OS);CHN anal.calcd percent: C:53.33; H: 4.44; N:15.55; Found: C: 53.45;H: 4.30; N:15.56.
Reference: [1] Oriental Journal of Chemistry, 2014, vol. 30, # 2, p. 469 - 477
  • 2
  • [ 55502-96-0 ]
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YieldReaction ConditionsOperation in experiment
79% at 130℃; for 0.166667 h; Microwave irradiation General procedure: A mixture of 1a,b ( 1 mmol) and formamide( 5-6 mmol) in ( 1 mmol) acetic acid, was irradiationin the microwave oven for 10 min. at (300 W) 130 °C.The reaction mixture was cooled and poured intoiced-cold water, filtered, washed and recrystallized from ethanol. 5,6-Dimethyl-3H-thieno[2,3-d]pyrimidin-4-one (4a) M.p. 180-183 °C; IR(cm-1): 3320, 1670; 1H-NMR(DMSO-d6) 1.7(s, 3H, CH3), 2.0(s, 3H, CH3),7.80 (1H, s, pyrimidine-H), 10.00 (br. s, 1H, NH);MS: m/z (percent), 180[M+] (95) (C8H8N2OS);CHN anal.calcd percent: C:53.33; H: 4.44; N:15.55; Found: C: 53.45;H: 4.30; N:15.56.
Reference: [1] Oriental Journal of Chemistry, 2014, vol. 30, # 2, p. 469 - 477
  • 3
  • [ 77287-34-4 ]
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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
  • 4
  • [ 3473-63-0 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5992 - 5994
  • 5
  • [ 32973-77-6 ]
  • [ 18593-44-7 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 432 - 433
  • 6
  • [ 74-90-8 ]
  • [ 4815-24-1 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 3, p. 496 - 500
  • 7
  • [ 99379-87-0 ]
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 432 - 433
  • 8
  • [ 4815-24-1 ]
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 432 - 433
  • 9
  • [ 77287-34-4 ]
  • [ 18593-44-7 ]
Reference: [1] Synthetic Communications, 2011, vol. 41, # 19, p. 2835 - 2851
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