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[ CAS No. 188577-68-6 ]

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Chemical Structure| 188577-68-6
Chemical Structure| 188577-68-6
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Product Details of [ 188577-68-6 ]

CAS No. :188577-68-6 MDL No. :MFCD07437842
Formula : C5H4Cl2N2 Boiling Point : 269.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :163.01 g/mol Pubchem ID :10773304
Synonyms :

Safety of [ 188577-68-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 188577-68-6 ]

  • Upstream synthesis route of [ 188577-68-6 ]
  • Downstream synthetic route of [ 188577-68-6 ]

[ 188577-68-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 188577-68-6 ]
  • [ 55934-01-5 ]
  • [ 856965-66-7 ]
Reference: [1] Patent: WO2010/122151, 2010, A1, . Location in patent: Page/Page column 66-67
  • 2
  • [ 19798-80-2 ]
  • [ 188577-69-7 ]
  • [ 55933-91-0 ]
  • [ 188577-68-6 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
[2] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
  • 3
  • [ 188577-71-1 ]
  • [ 188577-68-6 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride In water at 100℃; for 17 h; A mixture of 4,5-dichloro-2-trimethylacetamido-pyridine (0.500 g, 2.02 mmol) and aqueous HCl (6N; 9.5 ml) was heated was heated at 100° C. for 17 h. The reaction mixture was allowed to cool to room temperature, diluted with ice-water (15 ml), and the pH of the mixture was adjusted to 7.0 with 10percent aqueous NaOH. The white precipitate was collected by filtration, washed with water (2.x.5 ml), and dried in vacuo over P2O5. The title compound was obtained as a white solid (0.284 g, 86percent); 1H-NMR (500 Mz, DMSO-d6) 6.44 (s, 2H, NH2, exchangeable with D2O), 6.64 (s, 1H), and 8.03 (s, 1H) (3-H, 6-H); LC-MS (ESI, m/z) 4.37 min-163, 165, 167 [(M+H)+, Cl2 isotopic pattern].
85% With hydrogenchloride In water at 100℃; for 10 h; A mixture of N-(4,5-dichloropyridin-2-yl)pivalamide (1.25 g, 5.04 mmol) in 6N HCl (20 mL) was stirred at 100° C. for 10 h. The mixture was cooled, combined with water (20 mL), and basified by the addition of sodium bicarbonate solution (20 mL). The mixture was extracted with ethyl acetate (3×40 mL), and the combined organic layers were dried over sodium sulfate, then evaporated under reduced pressure and purified by gradient column chromatography using ethyl acetate in n-hexane as eluent to afford 4,5-dichloropyridin-2-amine as a white solid (0.7 g, 85percent). 1HNMR (400 MHz, CDCl3): δ 8.06 (s, 1H), 6.60 (s, 1H), 4.48 (br s, 2H). LC-MS calcd exact mass 161.98, found m/z 162.8 [M+H]+.
Reference: [1] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
[2] Patent: US2009/247507, 2009, A1, . Location in patent: Page/Page column 7
[3] Patent: US2016/362407, 2016, A1, . Location in patent: Paragraph 0558-0559
[4] Patent: WO2010/122151, 2010, A1, . Location in patent: Page/Page column 66
  • 4
  • [ 19798-80-2 ]
  • [ 188577-68-6 ]
YieldReaction ConditionsOperation in experiment
69% With N-chloro-succinimide In N,N-dimethyl-formamide at -20 - 20℃; for 24 h; 5.2.2.30
7,8-Dichloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (30)
To a solution of 2-amino-4-chloropyridine (1.28 g, 10.0 mmol) in DMF (40 mL) at -20 °C was added NCS (2.67 g, 20.0 mmol).
This mixture was allowed to warm to room temperature and stirred for 24 h, and then poured into 300 mL ice-water and extracted with ethyl acetate.
The extracts were washed with 1 M NaOH and brine, dried and evaporated.
The residue was purified by column chromatography on silica gel to give 4,5-dichloropyridin-2-amine (1.12 g, 69.0percent).
66% With N-chloro-succinimide In ethyl acetate at 20℃; for 28 h; INTERMEDIATE 1 4,5-Dichloropyridin-2-amine To a solution of 4-chloropyridine-2-amine (50.00 g, 0.389 mol) in EtOAc (400 mL) was added N-chloro succinimide (53.50 g, 0.401 mol) in one portion. The mixture was stirred over night (28 h) at room temperature, and was then filtered to remove precipitated succinimide. The filtrate was washed with aqueous 0.5M NaOH (8x50 mL), water (2x50 mL) and brine (2x50 mL). The organic phase was dried (Na2S04), filtered and evaporated to furnish 59.4 g of crude light brown powder after vacuum drying. The dry isolated crude (with a purity of ca. 75percent of the title compound) was slurried in hexane (800 mL) and stirred at reflux temperature for 15 min. The mixture was allowed to cool to 35 °C and was then filtered using a G3 glass frit filter. The filter cake was washed with hexane (ca. 200 mL) and dried on the filter to furnish 42.1 g (66percent>) of brown solid. The product was pure enough (96percent>) to be taken to the next step. 1H NMR (600 MHz, DMSO-d6) δ ppm 8.02 (s, 1 H) 6.65 (s, 1 H) 6.42 (s, 2 H). MS: (ESI+) m z 163, 165, 167 [M+H]+, di-chlorine isotopic pattern.
66% With N-chloro-succinimide In ethyl acetate at 20℃; for 28 h; To a solution of 4-chloropyridine-2-amine (50.00 g, 0.389 mol) in EtOAc (400 mL) was added N-chloro succinimide (53.50 g, 0.401 mol) in one portion. The mixture was stirred over night (28 h) at room temperature, and was then filtered to remove precipitated succinimide. The filtrate was washed with aqueous 0.5M NaOH (8x50 mL), water (2x50 mL) and brine (2x50 mL). The organic phase was dried (Na2SO4), filtered and evaporated to furnish 59.4 g of crude light brown powder after vacuum drying. The dry isolated crude (with a purity of ca. 75percent of the title compound) was slurried in hexane (800 mL) and stirred at reflux temperature for 15 min. The mixture was allowed to cool to 35 C and was then filtered using a G3 glass frit filter. The filter cake was washed with hexane (ca.200 mL) and dried on the filter to furnish 42.1 g (66percent) of brown solid. The product was pure enough (96percent) to be taken to the next step.1H NMR (600 MHz, DMSO-d6) δ ppm 8.02 (s, 1 H) 6.65 (s, 1 H) 6.42 (s, 2 H). MS: (ESI+) m/z 163, 165, 167 [M+H]+ , di-chlorine isotopic pattern.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 60 - 67
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 19 - 32
[3] Patent: WO2016/124553, 2016, A1, . Location in patent: Page/Page column 71-72
[4] Patent: WO2018/11138, 2018, A1, . Location in patent: Page/Page column 69-70
[5] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
[6] Patent: WO2011/85126, 2011, A2, . Location in patent: Page/Page column 162-163
[7] Patent: WO2011/85126, , A1, . Location in patent: Page/Page column 162-163[7] Patent: , 2011, , . Location in patent: Page/Page column 162-163
[9] Patent: US2016/362407, 2016, A1,
  • 5
  • [ 19798-80-2 ]
  • [ 188577-69-7 ]
  • [ 55933-91-0 ]
  • [ 188577-68-6 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
[2] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
  • 6
  • [ 188577-70-0 ]
  • [ 188577-68-6 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 5, p. 861 - 870
[2] Patent: US2016/362407, 2016, A1,
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