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[ CAS No. 615568-96-2 ] {[proInfo.proName]}

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Chemical Structure| 615568-96-2
Chemical Structure| 615568-96-2
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Product Details of [ 615568-96-2 ]

CAS No. :615568-96-2 MDL No. :MFCD18807799
Formula : C8H5FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :GGTMKHDQBKQAEP-UHFFFAOYSA-N
M.W : 164.14 Pubchem ID :21873634
Synonyms :

Safety of [ 615568-96-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 615568-96-2 ]

* 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 [ 615568-96-2 ]

[ 615568-96-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 615568-96-2 ]
  • (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride [ No CAS ]
  • [ 1075236-96-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-fluoro-1H-benzimidazole-2-carbaldehyde; (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride With sodium hydrogencarbonate; sodium sulfate In methanol; dichloromethane at 20℃; for 15h; Stage #2: With sodium tris(acetoxy)borohydride In methanol; dichloromethane at 25℃; for 4h; 46 Example 46; (lR)-l-[(4-[(4-Fluoro-lH-benzimidazol-2-yl)methyl]amino}-l- piperidinyl)methyl] - 1 ,2-dihydro-4H,9H-imidazo [ 1 ,2,3-//] -1 ,8-naphthyridine-4,9- dione dihydrochloride; To a 10 mL round-bottomed flask were added (li?)-l-[(4-amino-l- piperidinyl)methyl]-l,2-dihydro-4η,9η-imidazo[l,2,3-ij]-l,8-naphthyridine-4,9-dione (for a preparation see Example 5A(j)) (80 mg, 0.238 mmol), 4-fluoro-lH-benzimidazole- 2-carbaldehyde (for a synthesis see WO2003087098, Example 320) (42.9 mg, 0.261 mmol), and sodium bicarbonate (100 mg, 1.190 mmol) in DCM (4 ml) and methanol (1 ml) to give a brown suspension. Sodium sulfate (200 mg, 1.408 mmol) was added and the reaction was stirred at rt overnight. After 15h sodium triacetoxyborohydride (101 mg, 0.475 mmol) was added and the reaction was stirred at 25 0C under nitrogen for 4h. The reaction mixture was adsorbed onto silica and purified using 0 - 10% MeOH/DCM (1% NH4OH) to give the free base of the title compound. The LCMS and IH NMR were consistent with the desired product.1H NMR δH D-4 MeOH, (400MHz) 1.35-1.55 (m, 2H), 1.90- 1.96 (m, 2H), 2.30-2.41 (m, 2H), 2.71-2.81 (m, 2H), 2.91-2.99 (m,lH), 3.05-3.15 (m, 2H), 4.20 (s, 2H), 4.41-4.50 (m, 2H), 4.69 (s, 2H), 5.10-5.20 (m, IH), 6.25-6.36 (m, 2H), 6.91- 7.05 (m, IH), 7.16-7.25 (m, IH), 7.31-7.39 (m, IH), 7.75-7.81 (m, 2H), MS (ES+) m/z 449 (MH+). The free base of the title compound was taken up in 10% MeOH/DCM and treated with IN HCl to form the title compound as the diHCl salt (17 mg, 0.033 mmol, 13.73 % yield) .
  • 2
  • [ 615568-96-2 ]
  • (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride [ No CAS ]
  • (1R)-1-[(4-[(4-fluoro-1H-benzimidazol-2-yl)methyl]amino}-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; sodium sulfate / methanol; dichloromethane / 15 h / 20 °C 1.2: 4 h / 25 °C 2.1: hydrogenchloride / methanol; dichloromethane; water
  • 3
  • [ 615568-96-2 ]
  • [ 1075237-77-2 ]
  • [ 1075236-96-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-fluoro-1H-benzimidazole-2-carbaldehyde; (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione With sodium hydrogencarbonate; sodium sulfate In methanol; dichloromethane at 20℃; for 15h; Stage #2: With methanol; sodium tris(acetoxy)borohydride In dichloromethane at 25℃; for 4h; Inert atmosphere; 46 Example 46
(1R)-1-[(4-[(4-Fluoro-1H-benzimidazol-2-yl)methyl]amino}-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride To a 10 mL round-bottomed flask were added (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (for a preparation see Example 5A(j)) (80 mg, 0.238 mmol), 4-fluoro-1H-benzimidazole-2-carbaldehyde (for a synthesis see WO2003087098, Example 320) (42.9 mg, 0.261 mmol), and sodium bicarbonate (100 mg, 1.190 mmol) in DCM (4 ml) and methanol (1 ml) to give a brown suspension. Sodium sulfate (200 mg, 1.408 mmol) was added and the reaction was stirred at rt overnight. After 15 h sodium triacetoxyborohydride (101 mg, 0.475 mmol) was added and the reaction was stirred at 25° C. under nitrogen for 4 h. The reaction mixture was adsorbed onto silica and purified using 0-10% MeOH/DCM (1% NH4OH) to give the free base of the title compound. The LCMS and 1H NMR were consistent with the desired product. 1H NMR δH D-4 MeOH, (400 MHz) 1.35-1.55 (m, 2H), 1.90-1.96 (m, 2H), 2.30-2.41 (m, 2H), 2.71-2.81 (m, 2H), 2.91-2.99 (m, 1H), 3.05-3.15 (m, 2H), 4.20 (s, 2H), 4.41-4.50 (m, 2H), 4.69 (s, 2H), 5.10-5.20 (m, 1H), 6.25-6.36 (m, 2H), 6.91-7.05 (m, 1H), 7.16-7.25 (m, 1H), 7.31-7.39 (m, 1H), 7.75-7.81 (m, 2H), MS (ES+) m/z 449 (MH+).
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