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[ CAS No. 30235-28-0 ] {[proInfo.proName]}

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Chemical Structure| 30235-28-0
Chemical Structure| 30235-28-0
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Product Details of [ 30235-28-0 ]

CAS No. :30235-28-0 MDL No. :MFCD00490009
Formula : C8H7N3S Boiling Point : -
Linear Structure Formula :- InChI Key :CUSJGENRTWNHPV-UHFFFAOYSA-N
M.W : 177.23 Pubchem ID :930237
Synonyms :

Calculated chemistry of [ 30235-28-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.75
TPSA : 80.04 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.31
Solubility : 0.874 mg/ml ; 0.00493 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.591 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.148 mg/ml ; 0.000838 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 30235-28-0 ]

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 [ 30235-28-0 ]

* 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 [ 30235-28-0 ]
  • Downstream synthetic route of [ 30235-28-0 ]

[ 30235-28-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 5349-17-7 ]
  • [ 17356-08-0 ]
  • [ 30235-28-0 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 100℃; for 0.5 h; Biotage microwave
Stage #2: With sodium hydrogencarbonate In water
COMPOUND 3a4-(Pyridin-4-yl)thiazol-2-amine. Synthesis of batch 1. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.21 g, 7.90 mmol), thiourea (0.60 g, 7.90 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 °C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Synthesis of batch 2. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.54 g, 9.06 mmol), thiourea (0.69 g, 9.06 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 °C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Synthesis of batch 3. A mixture of 4-(bromoacetyl)pyridine hydrobromide (2) (2.16 g, 7.73 mmol), thiourea (0.58 g, 7.73 mmol) in anhydrous EtOH (10 ml) was stirred in a Biotage microwave at 100 °C for 30 min. After colling to room temperature, the solid precipitate was filtered, dried under vacuum.Batches 1, 2, and 3 were combined, suspended in an aqueous sat. solution of NaHC03 , filtered, dried under vacuum to provide the title compound as a pale pink solid (5.53 g, 31.27 mmol, 95percent), 1H NMR (400 MHz, CD3OD) δ 8.49 (d, J= 6.3 Hz, 2H), 7.79 (d, J= 6.3 Hz, 2H), 7.25 (s, 1H).
93%
Stage #1: Reflux
Stage #2: With ammonium hydroxide In ethanol; water for 2 h;
A mixture of 2-bromo-l-pyridin-4-yl-ethanone hydrobromide (10 g, 35.59 mmol) and thiourea (2.71 g, 35.59 mmol) in absolute EtOH (100 mL) was re fluxed overnight. After cooling, the reaction mixture was diluted with water (400 mL), the pH was adjusted to 11 with ammonium hydroxide solution, and it was further stirred for 2h. The resulting precipitate was filtered, washed with water, and dried in vacuo to provide 5.85 g of 4-(2-amino- thiazol-4-yl)-pyridine as a pinkish solid (93percent yield): 1H NMR (DMSO-dtf, ppm) δ 7.23 (broad s, 2H), 7.42 (s, 1H), 7.74 (d, 2H), 8.56 (d, 2H); [M+H]+ m/z 178
Reference: [1] MedChemComm, 2012, vol. 3, # 6, p. 699 - 709
[2] Patent: WO2011/130740, 2011, A2, . Location in patent: Page/Page column 42
[3] Patent: WO2012/125981, 2012, A2, . Location in patent: Page/Page column 131
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797
[5] Patent: WO2009/114552, 2009, A1, . Location in patent: Page/Page column 133
  • 2
  • [ 6221-13-2 ]
  • [ 17356-08-0 ]
  • [ 30235-28-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 1137 - 1141
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 560 - 564
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5028 - 5037
  • 3
  • [ 6221-13-2 ]
  • [ 30235-28-0 ]
Reference: [1] Patent: US2003/92720, 2003, A1,
  • 4
  • [ 1122-54-9 ]
  • [ 30235-28-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 560 - 564
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5028 - 5037
[3] Patent: WO2009/114552, 2009, A1,
  • 5
  • [ 53289-47-7 ]
  • [ 17356-08-0 ]
  • [ 30235-28-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1976, vol. 318, p. 875 - 877
  • 6
  • [ 1122-54-9 ]
  • [ 17356-08-0 ]
  • [ 30235-28-0 ]
Reference: [1] Chemische Berichte, 1959, vol. 92, p. 22,35
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