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[ CAS No. 21352-19-2 ] {[proInfo.proName]}

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Chemical Structure| 21352-19-2
Chemical Structure| 21352-19-2
Structure of 21352-19-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 21352-19-2 ]

CAS No. :21352-19-2 MDL No. :MFCD00223341
Formula : C7H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :170.60 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 21352-19-2 ]

* 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 [ 21352-19-2 ]

[ 21352-19-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 21352-19-2 ]
  • [ 4584-49-0 ]
  • [ 138768-69-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) DMF, 0 deg C, 10 min, 2.) 80 deg C, 1 h; Yield given. Multistep reaction;
  • 2
  • [ 21352-19-2 ]
  • [ 27483-92-7 ]
  • [ 138768-74-8 ]
  • 3
  • [ 21352-19-2 ]
  • [ 75449-26-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76.6 percent / activated copper bronze / dimethylformamide / 4 h / 110 °C 2: 95.2 percent / HCl / H2O / 0.5 h / Heating
Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / 3 h / 130 °C / Inert atmosphere; Schlenk technique 2: hydrogenchloride / water / 1 h / Reflux; Inert atmosphere; Schlenk technique
  • 4
  • [ 6298-19-7 ]
  • [ 75-36-5 ]
  • [ 21352-19-2 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃;
84% With triethylamine In tetrahydrofuran at 70℃; for 8h;
82% With triethylamine at 20℃; for 18h; Inert atmosphere; 1.1 The first step Dissolve 650 mg (A1, 5 mmol, 1.0 equiv.) of the commercially available compound 2-chloro-3-aminopyridine in 10 mL of triethylamine, and add 1 mL of acetyl chloride (15 mmol, 3.0 equiv.) under the protection of nitrogen, at room temperature After stirring for 3 h, 1 mL of acetyl chloride (15 mmol, 3.0 equiv.) was added, and the reaction was continued for 15 h at room temperature. TLC detected that the raw material was almost completely reacted. Add 50mL of water and 50mL of ethyl acetate for liquid separation extraction. The separated aqueous phase was extracted twice with 50mL of ethyl acetate. The combined organic phase was washed twice with 50mL of water. After drying, the solvent was evaporated to obtain 701mg of yellow oil B1. The yield is 82%, which can be directly used in the next reaction.
62% With triethylamine In dichloromethane The present invention is illustrated by the following examples, but is not limited to the details thereof. To a solution of 2chloro-3-aminopyridine (51.4 g, 400 mmol) in dichloromethane (800 mL) at 0° C. was added triethylamine (31.0 mL, 440 mmol) followed by acetyl chloride (62.0 mL, 440 mmol). The reaction was allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured into water (800 mL) and the layers were separated. The organic layer was treated with Darco-G-60 (activated charcoal), heated to reflux, filtered over Celite (diatomaceous earth manufactured by Celite Corp., Santa Barbara, Calif.) and concentrated to an oil. The oil was crystallized in diisopropyl ether and the solids were filtered to afford 42.4 g (62% yield) of N-(2-chloro-pyridin-3-yl)-acetamide. M. p.=81-83° C. 1 NMR (400 MHz, CDCl3) δ2.23 (s,3), 7.21 (dd, 1, J=8.1, 4.7) 7.67 (bs, 1), 8.06 (dd, 1, J=4.7, 1.3), δ8.66 (d, 1, J=7.9). 13C NMR (100 MHz, CDCl3) δ24.93, 123.34, 129.06, 131.89, 143.81, 144.08, 168.79.
62% With triethylamine In dichloromethane at 0 - 20℃;

  • 5
  • [ 39620-04-7 ]
  • [ 75-36-5 ]
  • [ 21352-19-2 ]
YieldReaction ConditionsOperation in experiment
N-(2-Chloropyridin-3-yl)acetamide (S-2) To a mixture of <strong>[39620-04-7]3-chloropyridin-2-amine</strong> (S-1) (12.8 g, 100 mmol) and Et3N (3 mL) in dried DCM (50 mL) was added acetyl chloride (8 mL) dropwise. The reaction was stirred at room temperature overnight, then adjusted to pH about 7 with an aqueous NaHCO3 solution, and extracted with DCM. The organic layer was washed with water, dried over Na2SO4, and concentrated to afford the title compound (17.1 g). MS (m/z): 171.6 (M+1)+.
  • 6
  • [ 21352-19-2 ]
  • [ 51013-67-3 ]
  • 4-(4-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); ruphos; In tert-butyl alcohol; at 110℃; for 18h; A 20 mL Biotage microwave vial loaded with Pd2(dba)3 (25.7 mg, 0.028 mmol), RuPhos (69.9 mg, 0.150 mmol), N-(2-chloropyridin-3-yl)acetamide 177-A (351 mg, 2.06 mmol), 4-(morpholinomethyl)aniline (400 mg, 1.872 mmol), K3PO4 (1.192 g, 5.62 mmol) and t-BuOH (4.68 mL) was capped, purged with argon, and heated to 110 C. for 18 h in an oil bath. The reaction was cooled, diluted with DCM, filtered through celite, concentrated, dryloaded onto silica gel and purified on a 12 g silica gel column (DCM/MeOH, 0-5%), affording 4-(4-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)morpholine 177 as a green oil (69 mg, 0.224 mmol, 12% yield, 5% MeOH in DCM). 1H NMR (CDCl3) delta: 8.28 (dd, J=4.9, 1.3 Hz, 1H), 7.99 (dd, J=8.0, 1.5 Hz, 1H), 7.55 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.27-7.19 (m, 1H), 3.82-3.71 (m, 4H), 3.58 (s, 2H), 2.55 (s, 3H), 2.53-2.43 (m, 4H)
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