Benzamide, N-[[(6-methyl-2-pyridinyl)amino]thioxomethyl]- synthesis
- Product Name:Benzamide, N-[[(6-methyl-2-pyridinyl)amino]thioxomethyl]-
- CAS Number:96938-51-1
- Molecular formula:C14H13N3OS
- Molecular Weight:271.34
1824-81-3
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96938-51-1
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Yield:96938-51-1 80%
Reaction Conditions:
in acetone; for 3 h;Reflux;
Steps:
N,N-dimethyl-4-(4-{2-[(6-methylpyridin-2-yl)amino]-1,3-thiazol-4-yl}phenyl)pyridin-2-amine
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 80%). 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 92%). 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,53%). 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 % yield.
References:
WO2013/33037,2013,A2 Location in patent:Paragraph 0752
1824-81-3
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333-20-0
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98-88-4
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96938-51-1
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65-85-0
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96938-51-1
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