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[ CAS No. 955368-90-8 ] {[proInfo.proName]}

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Chemical Structure| 955368-90-8
Chemical Structure| 955368-90-8
Structure of 955368-90-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 955368-90-8 ]

CAS No. :955368-90-8 MDL No. :MFCD19443206
Formula : C9H10N4OS Boiling Point : -
Linear Structure Formula :- InChI Key :JKBQCALHIQOSTC-UHFFFAOYSA-N
M.W : 222.27 Pubchem ID :67171470
Synonyms :

Calculated chemistry of [ 955368-90-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.27
TPSA : 88.87 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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 1.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.945 mg/ml ; 0.00425 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.272 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.553 mg/ml ; 0.00249 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 955368-90-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 955368-90-8 ]

* 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 [ 955368-90-8 ]
  • Downstream synthetic route of [ 955368-90-8 ]

[ 955368-90-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 955368-90-8 ]
  • [ 955365-80-7 ]
Reference: [1] ChemMedChem, 2018, vol. 13, # 16, p. 1681 - 1694
  • 2
  • [ 5909-24-0 ]
  • [ 21075-86-5 ]
  • [ 955368-90-8 ]
YieldReaction ConditionsOperation in experiment
51% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 72 h; Reflux DIPEA (20.8 ml, 120 mmol) and allyl hydrazine 5 (8.23 g, 47.8 mmol) were added to a solution of ethyl 4-chloro-2-methylthio- 5-pyrimidinecarboxylate (6; 1 1.1 g, 47.8 mmol) in THF (150 ml). The reaction mixture was heated at reflux for 72 h, before being concentrated in vacuo. Et20 (50 ml) was added to the residue, and the resultant precipitate was collected by filtration. The filtrate was evaporated to dryness, and the residue was cooled in an ice bath, after which TFA (40 ml) was added. The resultant solution was stirred at RT for 1 h, followed by 70 °C for 1 h. The solvent was removed in vacuo and the residue was dissolved in EtOH (50 ml) and cooled in an ice bath, after which 6M NaOH (75 ml) was added. The resultant solution was stirred at RT for 15 min, before 32 being acidified via the addition of cone. HCI (40 ml). The orange solution was evaporated to dryness and the resultant residue was partitioned between chloroform (100 ml) and water (100 ml), and the organic phase was washed with brine (50 ml), dried (Mg2S04), concentrated in vacuo, and triturated with hexanes. The solid precipitate was washed with EtOH and Et20, before being dried under vacuum to give the target compound as a yellow solid (5.44 g, 24.5 mmol, 51 percent). Rf 0.45 (9:1 DCM:MeOH); M.p. 125- 128 °C; IR (cm-1 ) 3032, 2979, 2926, 2659, 1656, 161 5, 1 566, 1 514; 1 H NMR (400 M Hz, DMSO-d6)2.53 (3H, s, -SCH3), 4.38 (2H, dapp, J = 5.2 Hz, N2-CH2), 5.06-5.20 (2H, m, allyl C-Hcis/trans), 5.87 (1 H, ddt, J = 17.2, 10.5, 5.3 Hz, alkene C-H), 8.67 (1 H, s, H-4), 12.65 (1 H, -1 ); MS [M + H] + m/z 223.1.
Reference: [1] Patent: WO2017/75629, 2017, A2, . Location in patent: Page/Page column 33; 34
[2] ChemMedChem, 2018, vol. 13, # 16, p. 1681 - 1694
[3] Patent: US2007/254892, 2007, A1, . Location in patent: Page/Page column 30-31
[4] Patent: WO2008/133866, 2008, A1, . Location in patent: Page/Page column 28
[5] ACS Chemical Biology, 2016, vol. 11, # 4, p. 921 - 930
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  • [ 638218-78-7 ]
  • [ 955368-90-8 ]
  • [ 955369-56-9 ]
Reference: [1] ChemMedChem, 2018, vol. 13, # 16, p. 1681 - 1694
[2] Patent: US2016/8361, 2016, A1, . Location in patent: Paragraph 0163
[3] ACS Chemical Biology, 2016, vol. 11, # 4, p. 921 - 930
[4] Patent: WO2017/75629, 2017, A2, . Location in patent: Page/Page column 34; 35
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