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Chemical Structure| 3719-45-7 Chemical Structure| 3719-45-7
Chemical Structure| 3719-45-7

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1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid is from Cordyceps bassiana, which is one of Cordyceps species with anti-oxidative, anti-cancer, anti-inflammatory, anti-diabetic, anti-obesity, anti-angiogenic, and anti-nociceptive activities. 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid targets to block AP-1-mediated luciferase activity, implying it has an anti-inflammatory function.

Synonyms: Nudifloric Acid

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Product Details of 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

CAS No. :3719-45-7
Formula : C7H7NO3
M.W : 153.14
SMILES Code : O=C(C(C=C1)=CN(C)C1=O)O
Synonyms :
Nudifloric Acid
MDL No. :MFCD00031002

Safety of 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

* 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 [ 3719-45-7 ]

[ 3719-45-7 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 3719-45-7 ]
  • [ 701-44-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate; In 1,4-dioxane; at 20℃; for 18h; To a solution of l-methyl-6-oxo-l,6-dihydropyridine-3-carboxylic acid (470 mg, 3.07 mmol) in 20 mL of dioxane was added Boc anhydride (1.34 g, 6.14 mmol), ammonium bicarbonate (485 mg, 6.14 mmol), and pyridine (0.496 mL, 6.14 mmol). The reaction mixture was stirred at ambient temperature for 18 h and then the resultant slurry was filtered to afford the title compound as a grey solid that was used in subsequent steps as is. MS: mlz = 153.1 [M+l]+.
  • 4
  • [ 3719-45-7 ]
  • [ 10561-91-8 ]
  • 5
  • [ 3719-45-7 ]
  • [ 412035-58-6 ]
  • 6
  • [ 6018-41-3 ]
  • [ 74-89-5 ]
  • [ 3719-45-7 ]
  • 8
  • [ 3719-45-7 ]
  • [ 162330-16-7 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 80℃; for 1h; A suspension of 1 -methyl-6-oxo-1 ,6-dihydropyridine-3-carboxylic acid (6.00 g, 39.2 mmol) in thionyl chloride (30 ml_) was heated to 80 C for 1 h. After being concentrated and dried in vacuo, the residue was dissolved in dry tetrahydrofuran (60 ml_). This solution was added dropwise to a mixture of 5-(3-fluorobenzyl)pyridin-2-amine (6.00 g, 30.2 mmol) and pyridine (7.20 ml_, 90.5 mmol) in dry tetrahydrofuran (60 ml_) at 0 C over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2 h. The white solid precipitate was collected by filtration and the filter cake was washed with ethanol (60 ml_) and ferf-butyl methyl ether (60 ml_). The filtrate was concentrated, and the resulting solid was washed with ethanol (60 ml_) and ferf-butyl methyl ether (60 ml_). Combined solids were dried in vacuo to give crude A/-(5-(3-fluorobenzyl)pyridin-2-yl)-1 -methyl-6-oxo-1 ,6-dihydropyridine-3-carboxamide (7.3 g). The crude material (7.3 g) was dissolved in ethanol (1 .10 L) at 80 C. After being filtered, the filtrate was concentrated, to about 300 ml_ and cooled down to room temperature. The solid was collected by filtration and the filter cake was washed with ethanol (50 ml_) and ferf-butyl methyl ether (50 ml_). The white solid was dried in vacuo to obtain A/-(5-(3-fluorobenzyl)pyridin-2-yl)-1 -methyl-6-oxo-1 ,6-dihydropyridine-3-carboxamide (5.05 g, 15.0 mmol, 49.7%).
  • 9
  • [ 6375-89-9 ]
  • [ 67-56-1 ]
  • [ 3719-45-7 ]
  • 10
  • [ 13441-42-4 ]
  • [ 3719-45-7 ]
  • [ 98279-50-6 ]
  • 11
  • [ 77837-12-8 ]
  • [ 3719-45-7 ]
  • 12
  • 3-(Carboxymethyl)-1-methylpyridiniumiodid [ No CAS ]
  • [ 3719-45-7 ]
  • 13
  • 3-(Carboxymethyl)-1-methylpyridiniumiodid [ No CAS ]
  • [ 3719-45-7 ]
  • [ 98279-50-6 ]
  • 1,6-Dihydro-1-methyl-6-oxo-3-pyridinessigsaeure [ No CAS ]
  • 1,2-Dihydro-1-methyl-2-oxo-3-pyridinessigsaeure [ No CAS ]
  • 14
  • [ 74-88-4 ]
  • [ 3719-45-7 ]
  • [ 6375-89-9 ]
YieldReaction ConditionsOperation in experiment
Example 261-Methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid Sodium hydride (2.87 g, 60percent, 71.8 mmol) was added slowly to methanol (62.5 mL) with stirring. 6-Hydroxy-nicotinic acid (5 g, 35.9 mmol) was added slowly, and the reaction mixture was heated to 62° C. Iodomethane (8.96 mL, 143.7 mmol) was added and the reaction was stirred overnight. The mixture was then cooled to room temperature and filtered to remove undissolved starting material. The filtrate was concentrated to yield a yellow powder which NMR analysis showed contained the title compound and methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate. This mixture was used in the subsequent reaction.1H NMR (300 MHz, (CD3)2SO): delta (ppm) 3.45 (s, 3H); 3.49 (s, 3H); 3.82 (s, 3H); 6.30 (d, 1H); 6.40 (d, 1H); 7.74-7.83 (m, 1H); 7.74-7.83 (m, 1H); 8.26 (d, 1H), 8.51 (d, 1H).
  • 15
  • [ 3719-45-7 ]
  • N-tert-butyl-4-<(1,2-dihydro-1-methyl-2-oxopyridine-5-yl)amido>benzamide [ No CAS ]
  • 16
  • [ 3719-45-7 ]
  • N,N-diisopropyl-4-<(1,2-dihydro-1-methyl-2-oxopyridine-5-yl)amido>benzamide [ No CAS ]
  • 17
  • [ 3719-45-7 ]
  • [ 6375-89-9 ]
  • 18
  • [ 6456-44-6 ]
  • [ 3719-45-7 ]
  • 19
  • [ 3719-45-7 ]
  • [ 153888-41-6 ]
  • 20
  • [ 3719-45-7 ]
  • 1-methyl-5-nitro-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 21
  • [ 55676-25-0 ]
  • [ 3719-45-7 ]
  • 22
  • [ 162330-26-9 ]
  • [ 3719-45-7 ]
  • 23
  • [ 498538-91-3 ]
  • [ 3719-45-7 ]
  • N-[(1S,2S)-2-amino-2-(4-fluorophenyl)-2-(6-fluoro-3-pyridyl)-1-methylethyl]-1-methyl-2-pyridone-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; at 20℃; for 3h; (1S,2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine (50 mg) and 1-methyl-2-pyridone-5-carboxylic acid (66 mg) were dissolved in pyridine (5 ML).To the solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (95 mg), and the mixture was stirred at room temperature for 3 hours.The reaction mixture was concentrated in vacuo, and the residue was dissolved in chloroform.The solution was washed with brine, dried over anhydrous sodium sulfate, and filtered to remove the sodium sulfate.The organic solvent was evaporated in vacuo, and the residue was purified by column chromatography on silica gel (chloroform:methanol=19:1) to give the title compound (100 mg).
  • 24
  • [ 3719-45-7 ]
  • [ 4732-69-8 ]
  • [ 89720-77-4 ]
  • [ 7440-66-6 ]
  • [ 1134916-85-0 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; Step 1: 5-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one To a suspension of <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid</strong> (606 mg) in CH2Cl2 (5 ml) were added one drop of N,N-dimethylformamide and oxalylchloride (803 mg). The mixture was stirred at room temperature for 1.5 h and was then concentrated to dryness. 1,2-Dimethoxyethane was added and the solvent was evaporated again to give the crude acid chloride. To a suspension of zinc powder (517 mg) in 1,2-dimethoxyethane (5 ml) was added tetrakis(triphenylphosphine)palladium(0) (55 mg). A suspension of the acid chloride in 1,2-dimethoxyethane (5 ml) was added. The mixture was cooled in an ice bath and a solution of 4-bromo-1-bromomethyl-2-chloro-benzene (1.125 g) in 1,2-dimethoxyethane (5 ml) was slowly added over 30 min. The mixture was stirred for 30 min at 0° C. and for 1.5 h at room temperature. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 7:3=>0:1) to give the title compound (603 mg, not completely pure) as a colorless solid. MS (m/e, ISP neg. ion)=338.0 [M-H+].
  • 25
  • [ 3719-45-7 ]
  • [ 89720-77-4 ]
  • [ 1134916-85-0 ]
YieldReaction ConditionsOperation in experiment
To a suspension of <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid</strong> (606 mg) in CH2Cl2 (5 ml) were added one drop of N,N-dimethylformamide and oxalylchloride (803 mg). The mixture was stirred at room temperature for 1.5 h and was then concentrated to dryness. 1,2-Dimethoxyethane was added and the solvent was evaporated again to give the crude acid chloride. To a suspension of zinc powder (517 mg) in 1,2-dimethoxyethane (5 ml) was added tetrakis(triphenylphosphine)palladium(0) (55 mg). A suspension of the acid chloride in 1,2-dimethoxyethane (5 ml) was added. The mixture was cooled in an ice bath and a solution of 4-bromo-1-bromomethyl-2-chloro-benzene (1.125 g) in 1,2-dimethoxyethane (5 ml) was slowly added over 30 min. The mixture was stirred for 30 min at 0° C. and for 1.5 h at room temperature. The mixture was filtered and the filtrate was concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 7:3=>0:1) to give the title compound (603 mg, not completely pure) as a colorless solid. MS (m/e, ISP neg. ion)=338.0 [M-H+].
  • 26
  • [ 3719-45-7 ]
  • [ 1172068-36-8 ]
  • [ 1196507-90-0 ]
YieldReaction ConditionsOperation in experiment
69% [00370] Step A: TEA (0.61 niL, 4.35 mmol) was added to 5-bromo-4-fluoro-lH- pyrrolo[2,3-b]pyridin-3-amine (0.20 g, 0.87 mmol, Example 1, Step H), l-methyl-6-oxo-l,6- dihydropyridine-3-carboxylic acid (0.17 g, 1.13 mmol) and BOP-Cl (0.33 g, 1.30 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 1 hour, and then a LiOH solution (3 mL, 2N) was added. The mixture was stirred for 30 minutes, and water (10 mL) was added. The solid formed was collected by filtration, washed with DCM (10 mL) and dried to give N-(5- bromo-4-fluoro-lH-pyrrolo[2,3-b]pyridin-3-yl)-l-methyl-6-oxo-l,6-dihydropyridine-3- carboxamide (0.22 g, 69percent yield) as a solid.
  • 27
  • [ 3719-45-7 ]
  • [ 90919-41-8 ]
  • [ 530-62-1 ]
  • [ 1246382-99-9 ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; Steps 1 and 2: 5-[2-(2-Chloro-5-methoxy-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one To a solution of <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid</strong> (7.95 g) in N,N-dimethylformamide (385 ml) was added 1,1'-carbonyldiimidazole (8.42 g). The mixture was stirred at 50° C. for 70 min. The mixture was cooled to -10° C. and (2-chloro-5-methoxy-phenyl)-acetic acid methyl ester (10.61 g) was added. Sodium hydride (60percent dispersion in mineral oil, 6.59 g) was added portionwise over 30 min. The mixture was slowly warmed to room temperature and stirred for 6 h. The mixture was poured into ice water (800 ml) and saturated aqueous ammonium chloride solution (250 ml) and was extracted with ethyl acetate (5*). The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness. The residue was dissolved in dimethylsulfoxide (100 ml). NaCl (3.15 g) and water (1.32 ml) were added and the mixture was heated to 140° C. for 5 h. After cooling to room temperature, ice water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness to give a light brown solid. The solid was washed with cyclohexane and a small amount of dichloromethane to give the title compound as a colorless solid. More product could be obtained by chromatographic purification of the mother liquor ((SiO2, cyclohexane/EtOAc 7:3=>EtOAc). Colorless solid (9.37 g). MS (m/e)=292.1 [M+H+].
  • 28
  • [ 3719-45-7 ]
  • [ 853569-69-4 ]
  • [ 1134916-85-0 ]
  • [ 1134916-90-7 ]
YieldReaction ConditionsOperation in experiment
Step 1: 5-[2-(2-Chloro-5-fluoro-4-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one In analogy to Example 165, step 1, <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid</strong> was converted to the acid chloride and subsequently reacted with 1-bromomethyl-2-chloro-5-fluoro-4-methoxy-benzene (CAS Reg. No. [853569-69-4]) to give the title compound. Off-white solid. MS (m/e)=310.2 [M+H+].
  • 29
  • [ 3719-45-7 ]
  • 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride [ No CAS ]
  • [ 76-05-1 ]
  • [ 883574-25-2 ]
YieldReaction ConditionsOperation in experiment
20% (4c) 4-(1-(3-Ethoxy-4-isopropoxyphenyl)-2-(N'-(1-methyl-6-oxo-1,6-dihydropyridine-3-carbonyl)hydrazino)-2-oxoethylamino)benzamidine trifluoroacetate [Show Image] 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (4 mg, 0.0872 mmol) was dissolved in N,N-dimethylformamide (0.25 ml) and cooled to 0°C. To the reaction mixture were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4 mg, 0.0209 mmol) and 1-hydroxybenzotriazole monohydrate (5 mg, 0.0326 mmol), followed by stirring for 1 hour and addition of 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride (10 mg, 0.0218 mmol) prepared in Example 4b and triethylamine (0.01 ml). After stirring the reaction mixture at room temperature for 3 days, it was directly purified by reversed-phase high performance liquid chromatography to give the title compound (2.8 mg, yield: 20percent). 1H-NMR (400 MHz, CD3OD) delta: 1.29 (d, J = 6.0 Hz, 6H), 1.39 (t, J = 6.8 Hz, 3H), 3.59 (s, 3H), 4.09 (q, J = 7.2 Hz, 2H), 4.52 (sept, J = 6.0 Hz, 1H), 5.14 (s, 1H), 6.53 (d, J = 9.6 Hz, 1H), 6.86 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 8.0 Hz, 1H), 7.10 (d, J = 8.0Hz, 1H), 7.21 (s, 1H), 7.63 (d, J = 8.8 Hz, 2H), 7.88 (d, J = 9.6 Hz, 1H), 8.30 (s, 1H); Mass spectrum (ESI) m/z: 521 (M+H)+
  • 30
  • [ 3719-45-7 ]
  • [ 1318757-72-0 ]
  • [ 1318756-56-7 ]
YieldReaction ConditionsOperation in experiment
44% To a solution of tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (500 mg, 1.4 mmol) obtained in Example 145-E) in ethanol (2 mL) was added concentrated hydrochloric acid (1 mL), and the mixture was stirred at 50°C for 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in DMF (3 mL), and <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid</strong> (257 mg, 1.68 mmol), HATU (638 mg, 1.68 mmol) and DIEA (0.144 mL, 0.84 mmol) were added. The reaction mixture was stirred at 60°C for 6 hr, diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: ethyl acetate-methanol]. The obtained resultant product was crystallized from ethyl acetate-heptane to give the title compound (240 mg) as a pale-brown solid (yield 44percent). MS (ESI+): [M+H]+ 392. 1H NMR (300MHz, CDCl3) delta2.41 (3H, s), 3.63 (3H, s), 4.19 (2H, s), 6.59 (1H, d, J = 9.5 Hz), 6.87-7.05 (2H, m), 7.10 (1H, s), 7.67 (1H, dd, J = 9.5, 2.7 Hz), 7.79 (1H, s), 8.22 (1H, d, J = 2.7 Hz).
  • 31
  • [ 3719-45-7 ]
  • [ 19335-11-6 ]
  • N-(1H-Indazol-5-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide [ No CAS ]
  • 32
  • [ 66171-50-4 ]
  • [ 3719-45-7 ]
  • 33
  • [ 6375-89-9 ]
  • [ 3719-45-7 ]
YieldReaction ConditionsOperation in experiment
80% With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 3h; To a solution of methyl 1 -methyl-6-oxo-1 ,6-dihydropyridine-3-carboxylate (1 .5 g, 8.97 mmol) in tetrahydrofuran (1 0 ml_) and water (10 ml_) at room temperature was added sodium hydroxide (1 .44 g, 35.9 mmol). The reaction mixture was stirred at room temperature for 3 h. The mixture was diluted with water (100 ml_), pH was adjusted to ~3-4 with aqueous 2 M hydrogen chloride and extracted with ethyl acetate (80 ml_ c 3). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford 1 -methyl-6-oxo-1 ,6-dihydropyridine-3-carboxylic acid (1 .1 g, 7.18 mmol, 80.0 %) as a white solid. LCMS (ESI) m/z: 154.1 [M+H]+.
  • 34
  • [ 3719-45-7 ]
  • N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine [ No CAS ]
  • 5-[3-benzyl-5-(4-methyl-piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-1-methyl-1H-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% 5-[3-Benzyl-5-(4-methyl-piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-1-methyl-1H-pyridin-2-one III-1 DIPEA (51 mg; 0.392 mmol) is added to a suspension of <strong>[3719-45-7]1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid</strong> D-7 (20 mg; 0.131 mmol) and HATU (70 mg; 0.183 mg) in DMF. The mixture is stirred at RT for 5 min. N2-Benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine E-3.1 is then added and the reaction mixture stirred at RT for 1 h. The reaction mixture is extracted with DCM and NaHCO3 solution. The organic layer is dried over Na2SO4 and concentrated in vacuum. To the formed amide is added 1 ml glacial acetic acid, the reaction is stirred at 120° C. for 2 days. The crude reaction mixture is purified by using reversed phase chromatography (Method: prep. HPLC 1). Yield: 30percent (16 mg; 0.039 mmol) HPLC-MS: (M+H)+=415; tRet=1.01 min; method LCMS BAS1
  • 35
  • [ 3719-45-7 ]
  • N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine [ No CAS ]
  • C24H28N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5- [3-Benzyl-5-(4-methyl-piperazin-1-yl)-3H-imidazo [4,5-bjpyridin-2-ylj -1-methyl-1H-pyridin-2-one III-1 DIPEA (51 mg; 0.392 mmol) is added to a suspension of 1-methyl-6-oxo-1,6- dihydro-pyridine-3-carboxylic acid D-7 (20 mg; 0.131 mmol) and HATU (70 mg;0.183 mg) in DMF. The mixture is stirred at RT for 5 mi N2-Benzyl-6-(4-methyl- piperazin- 1 -yl)-pyridine-2,3-diamine E-3. 1 is then added and the reaction mixture stirred at RT for lh. The reaction mixture is extracted with DCM and NaHCO3 solution. The organic layer is dried over Na2SO4 and concentrated in vacuum. To the formed amide is added 1 ml glacial acetic acid, the reaction is stirred at 120 °Cfor 2 days. The crude reaction mixture is purified by using reversed phase chromatography (Method: prep. HPLC 1).Yield: 30 percent (16 mg; 0.039 mmol)HPLC-MS: (M+H) = 415; tRet = 1.01 mm; method LCMS BAS1
 

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