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[ CAS No. 679806-84-9 ] {[proInfo.proName]}

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Chemical Structure| 679806-84-9
Chemical Structure| 679806-84-9
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Product Details of [ 679806-84-9 ]

CAS No. :679806-84-9 MDL No. :MFCD09064974
Formula : C11H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 218.64 Pubchem ID :-
Synonyms :

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Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

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* 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.

  • Downstream synthetic route of [ 679806-84-9 ]

[ 679806-84-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 199678-12-1 ]
  • [ 679806-84-9 ]
YieldReaction ConditionsOperation in experiment
84% With oxalyl dichloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 20℃; for 3.0h; Step B. N-(Pyridin-3-ylmethyl)-10-(4-pyrimidin-2-ylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide; To a solution of <strong>[199678-12-1]4-pyrimidin-2-ylbenzoic acid</strong> of Step A (0.283 g, 1.41 mmol) in dry tetrahydrofuran (20 mL) at room temperature under nitrogen was added N,N-dimethylformamide (1 drop, cat) followed by a 2.0 M solution of oxalyl chloride in dichloromethane (1.41 mmol, 2.82 mmol) and the reaction mixture was stirred at room temperature for 3 hours. The mixture was then concentrated in vacuo to afford 4-pyrimidin-2-yl-benzoyl chloride as a yellow syrup. The crude acid chloride was dissolved in dry tetrahydrof-uran (5 mL), added to a suspension of N-(pyridin-3-ylmethyl)-10,11-dihydro-5Hpyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 76, Step C (0.300 g, 0.942 mmol), and N,N-diisopropylethylamine (0.49 mL, 2.83 mmol) in dry tetrahydrofuran (5 mL), and the reaction mixture stirred at room temperature under nitrogen for 20 hours. The reaction was then quenched by the addition of 2 M sodium hydroxide (10 mL) and the mixture partitioned between ethyl acetate (50 mL) and 2 M sodium hydroxide (50 mL). The organic phase was separated, washed with 2 M sodium hydroxide (2×50 mL), water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a yellow foam. Purification by flash chromatography using a solvent gradient of 1 to 5% methanol in dichloromethane gave an cream foam that was crystallized from diethyl ether/hexane to afford the title compound (0.395 g, 84%) as white solid, m.p. 234-236 C. MS [(+)ESI, m/z]: 501 [M+H]+ Anal. Calcd for C30H24N6O2: C, 71.99; H, 4.83; N, 16.79. Found: C, 71.65; H, 4.91; N, 16.56.
With thionyl chloride; at 20 - 85℃; for 3.0h;Inert atmosphere; General procedure: Synthesis of amides from the carboxylic acid: A 100 mL round bottom flask was charged with carboxylic acid (11 mmol) to which thionyl chloride (10 mL) was added dropwise under flow of argon at room temperature. The reaction mixture was refluxed for 3 h at 85 C, then the excess SOCl2 was removed in vacuo to afford the crude acid chloride on one hand, whereas in another flask solution of 8-aminoquinoline (10 mmol) and NEt3 (11 mmol) in dichloromethane (20 mL) was stirred for 10-15 minutes. Deprotonated amine was added to a solution of acid chloride at 0 C. The reaction was allowed to warm to room temperature and stirred overnight for complete conversion. Upon completion, it was quenched with saturated NaHCO3 solution and extracted with CH2Cl2 three times. These extracts were combined and dried over NaSO4. After evaporation in vacuum, the crude amide product was purified by flash column chromatography (Hexane: ethyl acetate 10:1) through silica gel.
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