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Chemical Structure| 532-55-8 Chemical Structure| 532-55-8

Structure of 532-55-8

Chemical Structure| 532-55-8

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Product Details of [ 532-55-8 ]

CAS No. :532-55-8
Formula : C8H5NOS
M.W : 163.20
SMILES Code : O=C(N=C=S)C1=CC=CC=C1
MDL No. :MFCD00004815
InChI Key :CPEKAXYCDKETEN-UHFFFAOYSA-N
Pubchem ID :68284

Safety of [ 532-55-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H317-H318
Precautionary Statements:P261-P264-P270-P272-P280-P301+P310-P302+P352-P305+P351+P338-P310-P321-P330-P333+P313-P363-P405-P501
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of [ 532-55-8 ]

* 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 [ 532-55-8 ]
  • Downstream synthetic route of [ 532-55-8 ]

[ 532-55-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1824-81-3 ]
  • [ 532-55-8 ]
  • [ 96938-51-1 ]
YieldReaction ConditionsOperation in experiment
80% for 3 h; Reflux To the solution of benzylisothiocyanate (83.0 g, 509.3 mmol) in acetone (700mL) was added compound 6-methylpyridin-2 -amine (50 g, 463.0mmol) in acetone (600 ml) dropwise, then the reaction mixture was stirred at reflux for 3h. The reaction mixture was poured on to crushed ice, then filtered and washed with water, water/MeOH (1 : 1) and MeOH to give l-benzoyl-3-(6- methylpyridin-2-yl)thiourea as a yellow solid (100.1 g, yield 80percent). To a solution of 1-benzoyl-3-(6-methylpyridin-2-yl)thiourea (60 g,221.4 mmol) in THF ( 1000 ml) was added 2N NaOH (243.5ml), then heated at reflux for 3 h. Cooled to RT and filtered to give (6-methylpyridin-2- yl)thiourea as a white solid (34.1 g, yield 92percent). A mixture of (6-methylpyridin-2-yl)thiourea (13.2 g, 79.16 mmol) and 2-bromo-l-(4-bromophenyl)ethan-l-one (22 g, 79.16 mmol) in ethanol (300 mL) was stirred at reflux for 3h, then concentrated and purified with silica gel column to give N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine as a yellow solid (14.3 g,53percent). A solution of N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine (5 g. 14.5mmol), Bis(pinacolato)diboron (4.8 g, 18.8mmol), Pd(dppf)2Ci2 (1.2 mg, 1.5mmol) and AcOK (4.3 g, 43.3mmol) in dioxane (100ml) was heated to 80 under 2 overnight. The mixture was evaporated to give (6-methyl-N-{4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-l,3-thiazol-2-yl}pyridin-2-amine). Coupling (200mg) with 2-dimethylamino-4- bromopyridine under standard conditions gave 33 mg from 200 mg of, yellow solid, 17 percent yield.
References: [1] Patent: WO2013/33037, 2013, A2, . Location in patent: Paragraph 0752.
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 1, p. 137 - 140.
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3081 - 3085.
[4] Patent: WO2005/95345, 2005, A2, . Location in patent: Page/Page column 41.
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639.
[6] ChemMedChem, 2013, vol. 8, # 5, p. 847 - 857.
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6385 - 6397.
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 8, p. 1366 - 1377.
 

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