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[ CAS No. 324579-90-0 ] {[proInfo.proName]}

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Chemical Structure| 324579-90-0
Chemical Structure| 324579-90-0
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Product Details of [ 324579-90-0 ]

CAS No. :324579-90-0 MDL No. :MFCD01571854
Formula : C6H8N2S Boiling Point : -
Linear Structure Formula :- InChI Key :FGPNVCRMNYEMEP-UHFFFAOYSA-N
M.W : 140.21 Pubchem ID :674456
Synonyms :

Calculated chemistry of [ 324579-90-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.98
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 0.59
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 2.23 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (Ali) : -2.19
Solubility : 0.914 mg/ml ; 0.00652 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.51
Solubility : 4.36 mg/ml ; 0.0311 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 324579-90-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 324579-90-0 ]

* 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 [ 324579-90-0 ]
  • Downstream synthetic route of [ 324579-90-0 ]

[ 324579-90-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 69267-75-0 ]
  • [ 17356-08-0 ]
  • [ 324579-90-0 ]
YieldReaction ConditionsOperation in experiment
100% Heating / reflux EXAMPLE N; 4-Cyclopropyl-thiazol-2-ylamine; A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight. The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
100% Heating / reflux The 4-Cyclopropyl-thiazol-2-ylamine used in the above example was synthesised according to the following procedure:
A solution of 2-Bromo-1-cyclopropyl-ethanone (CAS [69267-75-0], Indian J. Chem. Sect. B, 22(9), 841(1983) (1 g, 6.1 mmol) and Thiourea (0.481 g, 6.1 mmol) in 15 ml of methanol was refluxed overnight.
The solvent was evaporated off and the title compound was obtained as an off-white solid (1.38 g, 100percent).
11 g With copper diacetate In ethanol at 80℃; for 1 h; To a stirred solution of 2-bromo-l-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)2 (0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80 °C for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHC03 (100 mL) to pH = 8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL x 2). The combined organic layers were washed with sat. NaHC03 (100 mL), brine (100 mL) and dried over anhydrous Na2S04. After filtration and concentration, the residue was purified by column chromatography (eluent: EA: PE = 1 :4) to afford the desired product J (1 1 g) as a yellow solid. 1H NMR (CDCl3-d, 400 MHz): δ ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).
11 g With copper diacetate In ethanol at 80℃; for 1 h; To a stirred solution of 2-bromo-1-cyclopropyl-ethanone (16 g, 100 mmol) in EtOH (150 mL) was added successively thiourea (8.0 g, 105 mmol) and Cu(OAc)2 (0.90 g, 5.0 mmol) at room temperature. After the mixture was heated at 80° C. for 1 hour, the solvent was removed under reduced pressure. The residue was neutralized with saturated NaHCO3 (100 mL) to pH=8-9, and then DCM (200 mL) was added. The organic layer was separated and the aqueous layer was further extracted with DCM (200 mL×2). The combined organic layers were washed with sat. NaHCO3 (100 mL), brine (100 mL) and dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by column chromatography (eluent: EA:PE=1:4) to afford the desired product J (11 g) as a yellow solid. 1H NMR (CDCl3-d, 400 MHz): δ ppm 6.06 (s, 1H), 4.86 (br s, 2H), 1.85-1.79 (m, 1H), 0.84-0.74 (m, 4H).

Reference: [1] Patent: US2006/160857, 2006, A1, . Location in patent: Page/Page column 56
[2] Patent: US2006/199960, 2006, A1, . Location in patent: Page/Page column 25
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3352 - 3371
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778
[5] Patent: WO2005/110980, 2005, A2, . Location in patent: Page/Page column 95
[6] Patent: WO2014/37480, 2014, A1, . Location in patent: Page/Page column 98; 99
[7] Patent: US2015/31687, 2015, A1, . Location in patent: Paragraph 0333; 0334
  • 2
  • [ 17356-08-0 ]
  • [ 324579-90-0 ]
Reference: [1] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 163-164
  • 3
  • [ 765-43-5 ]
  • [ 324579-90-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778
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