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[ CAS No. 543740-89-2 ] {[proInfo.proName]}

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Chemical Structure| 543740-89-2
Chemical Structure| 543740-89-2
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Product Details of [ 543740-89-2 ]

CAS No. :543740-89-2 MDL No. :MFCD12827873
Formula : C6H5IN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FKCUPIYQJSBUPO-UHFFFAOYSA-N
M.W : 264.02 Pubchem ID :11425541
Synonyms :

Safety of [ 543740-89-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 543740-89-2 ]

* 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 [ 543740-89-2 ]

[ 543740-89-2 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 536-74-3 ]
  • [ 76-05-1 ]
  • [ 543740-89-2 ]
  • 6-amino-5-phenylethynyl-nicotinamide; compound with trifluoro-acetic acid [ No CAS ]
  • 2
  • [ 536-74-3 ]
  • [ 543740-89-2 ]
  • 2-phenyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide [ No CAS ]
  • 3
  • [ 693-02-7 ]
  • [ 76-05-1 ]
  • [ 543740-89-2 ]
  • 6-amino-5-hex-1-ynyl-nicotinamide; compound with trifluoro-acetic acid [ No CAS ]
  • 4
  • [ 693-02-7 ]
  • [ 543740-89-2 ]
  • 2-butyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide [ No CAS ]
  • 5
  • [ 76-05-1 ]
  • [ 543740-89-2 ]
  • 6-amino-5-iodo-nicotinamide; compound with trifluoro-acetic acid [ No CAS ]
  • 6
  • [ 543740-75-6 ]
  • [ 543740-89-2 ]
  • 7
  • [ 39658-41-8 ]
  • [ 543740-89-2 ]
  • 8
  • (S)-S-methyl-S-phenylsulfoximine [ No CAS ]
  • [ 543740-89-2 ]
  • [ 1027729-81-2 ]
YieldReaction ConditionsOperation in experiment
71% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 60℃; for 5.16667h; Step 3 (S)-6-amino-5-iodo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamideTo a solution of <strong>[543740-89-2]6-amino-5-iodonicotinic acid</strong> (330 mg, 1.3 mmol), N, N- diisopropylethylamine (0.44 mL, 2.5 mmol), and (S)-(+)-S-methyl-S-phenylsulfoximine (291 mg, 1.9 mmol) in 7.0 mL DMF at room temperature was added BOP (608 mg, 1.4 mmol). The solution was stirred 10 minutes and then heated at 60 0C for 5 hours. The mixture was dissolved in EtOAc, washed with Na2CO3 solution, H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The brown oil was purified by chromatography (silica gel, hexane/acetone). The product containing fractions were purified by chromatography one additional time (silica gel, EtOAc/MeOH). To give the title compound as a white foam (354 mg, 71%).
  • 9
  • [ 211308-80-4 ]
  • [ 543740-89-2 ]
YieldReaction ConditionsOperation in experiment
65% Step 26-amino-5-iodonicotinic acidA solution of methyl 6-amino-5-iodonicotinate (723 mg, 2.6 mmol) and potassium hydroxide (729 mg, 13.0 mmol) in 40 mL methanol/H2O (3: 1 ratio) was heated at 50 0C. After 4 hours 10 mL THF was added and the reaction continued until 22 hours. The reaction was cooled to room temperature and concentrated HCl added until the solution was pH 4. The solution was concentrated to a volume of 15mL and the resulting precipitate filtered, rinsed with H2O and 40% EtOAc/hexane to give the title compound as a white solid (443mg, 65%).
1.77 g With water; potassium hydroxide; In tetrahydrofuran; at 50℃; for 48h; Preparation 4 6-Amino-5-iodonicotinic acid A mixture of methyl 6-amino-5-iodonicotinate, (2.78 g, 10 mmol, 1 eq) and potassium hydroxide (2.8 g, 5 eq) in THF/H2O (120 mL, 3:1) was heated at 50 C. for 48 hours. The reaction was then cooled to room temperature and concentrated HCl was drop wise added until a pH around 3-4 was achieved. The solution was concentrated and the resulting precipitate was collected by filtration to give the title compound as a slightly brown solid (1.77 g.) 1H NMR (DMSO-d6) δ: 12.64 (br. s., 1H), 8.47 (d, J=2.1 Hz, 1H), 8.25 (d, J=1.8 Hz, 1H), 6.88 (br. s., 2H)
  • 10
  • methyl 5-(S-methylsulfonimidoyl)pentanoate [ No CAS ]
  • [ 543740-89-2 ]
  • methyl 5-{N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.65 g With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70℃; for 1h; A solution of methyl 5-(S-methylsulfonimidoyl)pentanoate (2.32 g) was dissolved in anhydrous DMF (30 mL) and to this solution was added 5-iodo-6-amino-nicotinic acid (3.17 g, 1 eq), diisopropylethylamine (4.2 mL, 2 eq), and BOP (5.85 g, 1.1 eq). The reaction mixture was heated at 70 C. for 1 hour and then partitioned between EtOAc and aq NH4Cl. The organic layer was separated, washed sequentially with aq NH4Cl (1×), saturated aq NaHCO3 (1×), brine (1×), and dried with anhydrous Na2SO4 overnight. The upper solution layer was decanted, concentrated, and the brown oily reside was subject to column chromatography ( acetone-CHCl3 1:100 to MeOH-acetone-CHCl3 1:2:50). Concentration of the product eluting fractions provided the title compound as a slight yellow colored foam (2.65 g). 1H NMR (DMSO-d6) δ: 8.52 (d, J=2.1 Hz, 1H), 8.31 (d, J=1.9 Hz, 1H), 6.72 (br. s., 2H), 3.52-3.63 (m, 5H), 3.38 (s, 3H), 2.39 (t, J=7.2 Hz, 2H), 1.61-1.86 (m, 4H)
  • 11
  • [ 543740-89-2 ]
  • 6-amino-5-[(3-aminophenyl)ethynyl]-N-[dimethyl(oxido)-λ4-sulfanylidene]nicotinamide [ No CAS ]
  • 12
  • [ 543740-89-2 ]
  • 6-amino-N-[dimethyl(oxido)-λ4-sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide [ No CAS ]
  • 13
  • [ 543740-89-2 ]
  • 6-amino-N-[2-(3-hydroxypyrrolidin-1-yl)-2-oxoethyl](methyl)oxido-λ4-sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide [ No CAS ]
  • 6-amino-N-[2-(3-hydroxypyrrolidin-1-yl)-2-oxoethyl](methyl)oxido-λ4-sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide [ No CAS ]
  • 14
  • [ 1520-31-6 ]
  • [ 543740-89-2 ]
  • 6-amino-N-[dimethyl(oxido)-λ4-sulfanylidene]-5-iodonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; In N,N-dimethyl-formamide; at 70℃; for 1.5h;Inert atmosphere; To a 250 mL round bottom flask containing 5-iodo-6-amino-nicotinic acid (5 g, 18.9 mmol) and dimethylsulfoximine (1.94 g, 1.1 eq) in anhydrous DMF (50 mL) was added diisopropylamine (6.6 mL, 2 eq) and BOP (9.21 g, 1.1 eq) under nitrogen atmosphere. The reaction mixture was heated at 70 C. for 1.5 hours and then partitioned between aq NH4Cl and EtOAc. The aqueous layer was separated and extracted once with EtOAc. The two organic layers were combined, and washed with saturated aq NaHCO3/brine (1:1, 1×), brine (1×), and dried with anhydrous Na2SO4. The solution layer was decanted, concentrated, and the brown solid residue was treated with EtOAc with stirring at RT for 30 minutes. The solid which formed was colleded by filtration and dried to give the title compound as an offwhite solid (5.31 g, 83%).
  • 15
  • ethyl(S-methylsulfonimidoyl)acetate [ No CAS ]
  • [ 543740-89-2 ]
  • ethyl {N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
24 mg With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; In N,N-dimethyl-formamide; at 70℃; for 6h; A solution of ethyl(S-methylsulfonimidoyl)acetate was dissolved in anhydrous DMF (1 mL) and treated with 5-iodo-6-amino-nicotinic acid (82 mg, 1.05 eq), diisopropylamine (0.1 mL, 2 eq), and BOP (149 mg, 1.1 eq) with stirring. The reaction mixture was heated to 70 C. for 6 hours and then partitioned between EtOAc and aq NH4Cl. The organic layer was separated, washed with saturated aq NaHCO3 (1×) and brine (1×), and dried over Na2SO4. The organic phase was filtered and concentrated. The residue as purified by gradient column chromatography (EtOAc-Hexane 1:9 to 2:3). Concentration of the product containing fractions provided the title compound as a brown oil (24 mg).
  • 16
  • ethyl(S-methylsulfonimidoyl)acetate [ No CAS ]
  • [ 543740-89-2 ]
  • ethyl(N-[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)acetate [ No CAS ]
  • 17
  • [ 543740-89-2 ]
  • 6-amino-N-(4-oxido-1,4λ6-oxathian-4-ylidene)-5-[(trimethylsilyl)ethynyl]nicotinamide [ No CAS ]
  • 18
  • [ 543740-89-2 ]
  • 6-amino-5-[3-([4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)phenyl]ethynyl}-N-(4-oxido-1,4λ4-oxathian-4-ylidene)nicotinamide [ No CAS ]
  • 19
  • [ 543740-89-2 ]
  • 6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)-N-(4-oxido-1,4λ6-oxathian-4-ylidene)nicotinamide [ No CAS ]
  • 20
  • [ 708257-15-2 ]
  • [ 543740-89-2 ]
  • 6-amino-5-iodo-N-(4-oxido-1,4λ6-oxathian-4-ylidene)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 20h; Preparation 5 6-amino-5-iodo-N-(4-oxido-1,4λ4-oxathian-4-ylidene)nicotinamide To a solution of 1,4-oxathiane (510 mg, 3.21 mmol, 1.05 eq) in anhydrous DMF (8 mL) was added <strong>[543740-89-2]6-amino-5-iodonicotinic acid</strong> (806 mg, 1.0 eq), diisopropylethylamine (1.1 mL, 2 eq), and BOP (1.484 g, 1.1 eq). The reaction mixture was heated at 60 C. for 20 hours and then partitioned between EtOAc and aq NH4Cl. The organic layer was separated, washed further with saturated aq NaHCO3 (1*), brine (1*), and dried with anhydrous Na2SO4 overnight. The upper solution layer was decanted, concentrated, and the brown oily reside was subject to column chromatography (EtOAc-Hex 1:5 to 3:1). Concentration of the product eluting fractions gave the title compound as white solid (889 mg, 77%). 1H NMR (DMSO-d6) δ: 8.57 (d, J=2.1 Hz, 1H), 8.35 (d, J=2.1 Hz, 1H), 6.78 (br. s., 2H), 4.10-4.15 (m, 2H), 3.91 (ddd, J=12.6, 8.5, 2.1 Hz, 2H), 3.79-3.84 (m, 2H), 3.55-3.60 (m, 2H)
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