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Chemical Structure| 1177415-90-5 Chemical Structure| 1177415-90-5

Structure of 1177415-90-5

Chemical Structure| 1177415-90-5

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Product Details of [ 1177415-90-5 ]

CAS No. :1177415-90-5
Formula : C9H7Cl2N3O2
M.W : 260.08
SMILES Code : O=C(C1=CN=C2C(Cl)=CC(Cl)=NN21)OCC
MDL No. :MFCD31556383
InChI Key :PFVAGCVRRYYJLB-UHFFFAOYSA-N
Pubchem ID :59314032

Safety of [ 1177415-90-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 1177415-90-5 ]

* 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 [ 1177415-90-5 ]

[ 1177415-90-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 446273-59-2 ]
  • [ 33142-21-1 ]
  • [ 1177415-90-5 ]
  • [ 1177415-89-2 ]
YieldReaction ConditionsOperation in experiment
at 90℃; for 16h; To a 250 mL round-bottomed flask was added ethyl 2-chloro-3- oxopropanoate (4.33 g, 28.8 mmol) and 4-bromo-6-chloropyridazin-3-amine (5 g, 23.99 mmol). The solution was heated to 90 0C for 16 hours. The solution was quenched with ethyl acetate and washed with water. The organic layer was dried <n="48"/>over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by ISCO (10 % ethyl acetate / dichloromethane; 80 g column) to give a mixture of ethyl 8-bromo-6-chloroimidazo[l,2-b]pyridazine-3-carboxylate and ethyl 6,8-dichloroimidazo[l,2-b]pyridazine-3-carboxylate (2.1 g, 29 % yield). LC/MS, m/z 256.96 (M+l). HPLC Rt, 2.54 min. LC/MS, m/z 303.92 (M+l). HPLC Rt, 2.63 min. Waters Sunfire C18 column (4.6 x 50 mm). 0%-100%B. Solvent B: (90% MeOH, 10 % H2O, 0.1% TFA). Solvent A: (10% MeOH, 90 % H2O, 0.1% TFA). Gradient, start %B = 0, final % B = 100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.
at 90℃; for 16h; 1C: Preparation of ethyl 8-bromo-6-chloroimidazo[l,2-b]pyridazine-3-carboxylate and ethyl 6,8-dichloroimidazo[l,2-b]pyridazine-3-carboxylate[00230] To a 250 mL round-bottomed flask was added IB (4.33 g, 28.8 mmol) and IA (5 g, 24.0 mmol). The solution was heated to 90 0C for 16 hours. The solution was quenched with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude was purified by flash chromatography (SiC^, 10 % ethyl acetate / DCM; 80 g column) to give a mixture of IC-I and lC-2 (2.1 g, 29 % yield). [00231] IC-I : HPLC: Rt = 2.54 min (Waters Sunfire C18 column (4.6 x 50 mm). 10-90% aqueous methanol containing 0.1% TF A; 4 min gradient, flow rate = 4 mL/min, detection at 254 nm). MS (ES): m/z = 256.96 [M+H]+. [00232] lC-2: HPLC: Rt = 2.63 min (Waters Sunfire C18 column (4.6 x 50 mm). 10-90% aqueous methanol containing 0.1% TF A, 4 min gradient, flow rate = 4 mL/min, detection at 254 nm). MS (ES): m/z = 303.92 [M+H]+.
In ethanol; at 80℃; for 16h; To a solution of 4-bromo-6-chloropyridazin-3-amine (175 g, 840 mmol) in ethanol (2 L) was added <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> (202 g, 1343 mmol) and the reaction was heated to 80 C for 16 hours. The solvent was removed in vacuo and the residual material was diluted with water and dichloromethane. The biphasic mixture was passed through a celite bed and the filtrate was separated into two layers. The dichloromethane layer was separated and then washed with water and saturated aqueous sodium chloride (brine), it was then dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified using silica gel chromatography (0 to 20% ethyl acetate in petroleum ether). The product fractions were dried and then triturated with 10% methyl tert-butyl ether in petroleum ether (500 mL). The product was filtered off and rinsed with petroleum ether to provide the product (73 g, 33% yield) as a mixture of the C8-bromo and C8-chloro species (-80:20), the mixture was used as such in the subsequent steps (referred to as the chloride for simplicity). NMR (300 MHz, CDCh): (0447) Chloro: delta 8.37 (s, 1H), 7.38 (s, 1H), 4.47 (q, J = 7.2 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H). Bromo: delta 8.38 (s, 1H), 7.57 (s, 1H), 4.47 (q, J = 7.2 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H). LC retention time chloro: 1.04 min [O] ; bromo: 1.07 [O]. Mass Spectrometry ("MS") (E+) m/z: 260 (chloro); 304 (bromo) (MH+).
In ethanol; at 80℃; for 16h; To a solution of 4-bromo-6-chloropyridazin-3-amine (175 g, 840 mmol) inethanol (2 L) was added <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> (202 g, 1343 mmol) and thereaction was heated to 80 C for 16 hours. The solvent was removed in vacuo and the residual material was diluted with water and dichloromethane. The biphasic mixture was passed through a celite bed and the filtrate was separated into two layers. The dichloromethane layer was separated and then washed with water and saturated aqueoussodium chloride (brine), it was then dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified using silica gel chromatography (0 to 20% ethyl acetate in petroleum ether). The product fractions were dried and then triturated with 10% methyl tert-butyl ether in petroleum ether (500 mL). The product was filtered off and rinsed with petroleum ether to provide la (73 g, 33% yield) as a mixtureof the C8-bromo and C8-chloro species (80:20), the mixture was used as such in the subsequent steps (referred to as the chloride for simplicity).?H NMR (300 MHz, CDC13): Chloro: 8.37 (s, 1H), 7.38 (s, 1H), 4.47 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H).Bromo: 8.38 (s, 1H), 7.57 (s, 1H), 4.47 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H).LC retention time chloro: 1.04 mm [Bj; bromo: 1.07 [Bj. Mass Spectrometry (?MS?)(E+) m/z: 260 (chloro); 304 (bromo) (MH).
In ethanol; at 80℃; for 16h; To a solution of 4-bromo-6-chloropyridazin-3-amine (175 g, 840 mmol) in ethanol (2 L) was added <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> (202 g, 1343 mmol) and the reaction was heated to 80 C for 16 hours. The solvent was removed in vacuo and the residual material was diluted with water and dichloromethane. The biphasic mixture was passed through a celite bed and the filtrate was separated into two layers. Thedichloromethane layer was separated and then washed with water and saturated aqueous sodium chloride (brine), it was then dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified using silica gel chromatography (0 to 20% ethyl acetate in petroleum ether). The product fractions were dried and then triturated with 10% methyl tert-butyl ether in petroleum ether (500 mL). The product wasfiltered off and rinsed with petroleum ether to provide the product (73 g, 33% yield) as a mixture of the C8-bromo and C8-chloro species (80:20); the mixture was used as such in the subsequent steps (referred to as the chloride for simplicity).?H NMR (300 MHz, CDC13):Chloro: 8.37 (s, 1H), 7.38 (s, 1H), 4.47 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H). Bromo: 8.38 (s, 1H), 7.57 (s, 1H), 4.47 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H). LC retention time chloro: 1.04 mm [Gj; bromo: 1.07 [Gj. Mass Spectrometry (?MS?) (E+)m/z: 260 (chloro); 304 (bromo) (MH).

 

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