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Structure of 59237-53-5

Chemical Structure| 59237-53-5

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Product Details of [ 59237-53-5 ]

CAS No. :59237-53-5
Formula : C7H5ClN2O4
M.W : 216.58
SMILES Code : O=C(OC)C1=CN=C(Cl)C([N+]([O-])=O)=C1
MDL No. :MFCD01928341
Boiling Point : No data available
InChI Key :BRPREIDVQXJOJH-UHFFFAOYSA-N
Pubchem ID :346961

Safety of [ 59237-53-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 59237-53-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 49.35
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

85.01 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.29
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.5
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.43
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.1
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.25
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.77

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.25
Solubility 1.23 mg/ml ; 0.00566 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.89
Solubility 0.277 mg/ml ; 0.00128 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.11
Solubility 1.7 mg/ml ; 0.00783 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.56 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

3.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.06

Application In Synthesis of [ 59237-53-5 ]

* 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 [ 59237-53-5 ]

[ 59237-53-5 ] Synthesis Path-Downstream   1~35

  • 3
  • 5-nitro-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [ No CAS ]
  • [ 59237-53-5 ]
  • 4
  • [ 59237-53-5 ]
  • [ 166742-22-9 ]
  • [ 59237-49-9 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; water; sodium thiomethoxide; REFERENCE EXAMPLE 44 A solution of sodium methoxide in methanol (82.65 ML; 1 M) is added slowly to a stirred solution of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (17 g) in anhydrous methanol (250 ML) and the mixture is stirred for 8 hours. The mixture is concentrated, and the residue is treated with water and extracted with ethyl acetate. The extract is washed with water, treated with decolourising charcoal, and dried over magnesium sulphate. Concentration gives methyl 6-methoxy-5-nitronicotinate (9.8 g), in the form of an orange solid. Recrystallization from cyclohexane gives white needles, m.p.118-119°C. By proceeding in a similar manner using sodium thiomethoxide instead of sodium methoxide as the starting material, there is prepared methyl 6-methylthio-5-nitronicotinate.
  • 5
  • [ 59237-53-5 ]
  • [ 2365-48-2 ]
  • [ 443955-70-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 1h; A solution of 6-chloro-5-nitro-nicotinic acid methyl ester [(L.] [OG)] [prepared as described by A. H. Berne et [AL. J. CHEM. SOC.] 2590-2594 (1951)] in dichloromethane (10 mL) containing triethylamine (0.76 mL) was treated with mercapto-acetic acid methyl ester (0.44 mL) and the solution was stirred at room temperature for 1 hour and evaporated to dryness. Sodium bicarbonate solution was added and the mixture was extracted with dichloromethane, dried (anhydrous sodium sulfate) and evaporated to afford a solid [(L.] [OG).] MS (+ve ion electrospray) m/z 287 (MH+).
With triethylamine; In dichloromethane; at 20℃; for 1h; A solution of 6-chloro-5-nitro-nicotinic acid methyl ester (l. Og) [prepared as described by A. H. Berrie et al. J. Chem. Soc. 2590-2594 (1951)] in dichloromethane (lOmL) containing triethylamine (0.76mL) was treated with mercapto-acetic acid methyl ester (0.44mL) and the solution was stirred at room temperature for 1 hour and evaporated to dryness. Sodium bicarbonate solution was added and the mixture was extracted with dichloromethane, dried (anhydrous sodium sulfate) and evaporated to afford a solid (l. Og). MS (+ve ion electrospray) m/z 287 (MH+).
  • 6
  • [ 59237-53-5 ]
  • [ 51388-20-6 ]
  • [ 847777-84-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; To a solution of 6-chloro-5-nitro-nicotinic acid methyl ester (216mg, 1. OMMOL) and 4- benzyloxyaniline hydrochloride (280mg, 1. 2MMOL) in MEOH (LOML) was added PR2NET (0.35mL, 2. 0MMOL). The resulting mixture was stirred at rt overnight, a red solid precipitated from the mixture, which was collected by filtration. MS (ES, Pos. ) : m/z 380 [MH+]. 1H NMR (CDC13, 400 MHz) : 8 = 3.94 (s, 3H), 5.10 (s, 2H), 7.03 (d, J= 8. 8 Hz, 2H), 7.38-7. 46 (M, 5H), 7.50 (d, J= 8. 8 Hz, 2H), 9.01 (d, J= 2.0 Hz, 1H), 9.08 (d, J= 2.0 Hz, 1H), 10.2 (br s, 1H).
With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; 6-(4-Benzyloxyphenylamino)-5-nitronicotinic acid methyl ester (XXIV): To a solution of 6-chloro-5-nitro-nicotinic acid methyl ester (216 mg, 1.0 mmol) and 4-benzyloxyaniline hydrochloride (280 mg, 1.2 mmol) in MeOH (10 mL) was added iPr2NEt (0.35 mL, 2.0 mmol). The resulting mixture was stirred at rt overnight, a red solid precipitated from the mixture, which was collected by filtration. MS (ES, Pos.): m/z 380 [MH+]. 1H NMR (CDCl3, 400 MHz): delta=3.94 (s, 3H), 5.10 (s, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.38-7.46 (m, 5H), 7.50 (d, J=8.8 Hz, 2H), 9.01 (d, J=2.0 Hz, 1H), 9.08 (d, J=2.0 Hz, 1H), 10.2 (br s, 1H).
  • 7
  • [ 67-56-1 ]
  • [ 59237-53-5 ]
YieldReaction ConditionsOperation in experiment
A suspension of 6- hydroxy-5-nitro-nicotinic acid (1. 1 g, 6. 0MMOL) and PC15 (3.75g, 18. 0MMOL) in POC13 (5 mL) was stirred at 100°C for 2H. Excessive phosphorus oxychloride was evaporated under reduced pressure. The residue was dissolved in 1 OML of anhydrous ether and cooled to 0°C, then 10mL of methanol was added dropwise. L OMIN later, the ether was evaporated under reduced pressure at rt. The remaining methanol solution was diluted with water (40ML), and the light-yellow solid was collected by filtration. 1H NMR (CDC13, 400 MHz): 8 = 4.03 (s, 3H), 8.77 (d, J= 2.1 Hz, 1H), 9.18 (d, J= 2.1 Hz, 1H).
6-Chloro-5-nitronicotinic acid methyl ester (XXIII): A suspension of 6-hydroxy-5-nitro-nicotinic acid (1.1 g, 6.0 mmol) and PCl5 (3.75 g, 18.0 mmol) in POCl3 (5 mL) was stirred at 100° C. for 2 h. Excessive phosphorus oxychloride was evaporated under reduced pressure. The residue was dissolved in 10 mL of anhydrous ether and cooled to 0° C., then 10 mL of methanol was added dropwise. 10 min later, the ether was evaporated under reduced pressure at rt. The remaining methanol solution was diluted with water (40 mL), and the light-yellow solid was collected by filtration. 1H NMR (CDCl3, 400 MHz): delta=4.03 (s, 3H), 8.77 (d, J=2.1 Hz, 1H), 9.18 (d, J=2.1 Hz, 1H).
  • 8
  • [ 59237-53-5 ]
  • [ 30766-26-8 ]
YieldReaction ConditionsOperation in experiment
90% With hydrazine; In 1,4-dioxane; at 15 - 25℃; for 3h; B. 6-Hydrazino-5-nitro-nicotinic acid methyl ester; To a at 15°C cooled solution of 30.0 g (0.14 mol) 6-chloro-5-nitro-nicotinic acid methyl ester in dioxane (600mi) is added hydrazine hydrate (21.5 ml). During the addition the reaction mixture is warmed up to 25°C and is stirred for further 3 h. The reaction is quenched by pouring the reaction mixture into a saturated aqueous ammonium chloride solution. The precipitated solid is filtered off and dried under vacuo at 50°C to give 26.5 g (0.12 mol/90 percent) of the title compound as a red solid.
90% With hydrazine; In 1,4-dioxane; at 15 - 25℃; for 3h; To a at 15°C cooled solution of 30.0 g (0.14 mol) 6-chloro-5-nitro-nicotinic acid methyl ester in dioxane (600ml) is added hydrazine hydrate (21.5 ml) During the addition the reaction mixture is warmed up to 25°C and is stirred for further 3 h. The reaction is quenched by pouring the reaction mixture into a saturated aqueous ammonium chloride solution. The precipitated solid is filtered off and dried under vacuo at 50°C to give 26.5 g (0.12 mol/90 percent) of the title compound as a red solid. 'H-NMR (200MHz, d"-DMSO) : 8 = 3.85 (s, 3 H), 8.69 (d, 1 H), 8.90 (d, 1 H).
  • 9
  • [ 67-56-1 ]
  • [ 7477-10-3 ]
  • [ 59237-53-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 0℃; To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60°C until the evolution of gaz has ended. Then it is stirred at 80°C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the title compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol).
  • 10
  • [ 59237-53-5 ]
  • [ 59237-49-9 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; water; REFERENCE EXAMPLE 17 Sodium methoxide in methanol (82.65 mL of a 1 M solution) is added slowly to a stirred solution of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (17 g) in anhydrous methanol (250 mL) and the mixture stirred for 8 hours. The mixture is concentrated, the residue treated with water and then extracted into ethyl acetate. The extracts are washed with water, treated with decolourising charcoal and dried (MgSO4). Concentration afforded methyl 6-methoxy-5-nitronicotinate (9.8 g) as an orange solid. Recrstallisation from cyclohexane afforded white needles, m.p.118-9° C.
  • 11
  • [ 59237-53-5 ]
  • [ 203661-13-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydrogensulfide; In methanol; di-isopropyl ether; Production Example 105 Methyl 5-amino-6-mercaptonicotinate To a solution of 6 g of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> in methanol (100 ml) was added 6.7 g of sodium hydrogensulfide and the resulting mixture was heated under reflux for 2 hours. After distilling off the solvent under reduced pressure, dilute hydrochloric acid was added to the residue followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 24.7 g of the title compound as yellow crystals. 1H-NMR(DMSO-d6) delta ppm: 3.78(s, 3H),5.91-6.00(br.s, 2H), 7.12(d, J=2.0 Hz, 1H), 7.53(dd, J=2.0, 6.4 Hz, 1H)
  • 12
  • [ 59237-53-5 ]
  • [ 211915-52-5 ]
YieldReaction ConditionsOperation in experiment
In methylamine; a Methyl 6-methylamino-5-nitro-nicotinate 1.6 g (7.4 mMol) of methyl 6-chloro-5-nitro-nicotinate (see Bernie et al. in J. Chem. Soc. 1951, 2590) were stirred in 20 ml of 40percent aqueous methylamine solution at room temperature for 30 minutes. The reaction mixture was then diluted with ice water, the yellow precipitate formed was filtered off and dried. Yield: 1.2 g (80percent of theory), Rf value: 0.66 (silica gel; ethyl acetate/ethanol/glacial acetic acid=90:5:5)
  • 13
  • [ 59237-53-5 ]
  • [ 7439-89-6 ]
  • [ 211915-96-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; water; a Methyl 5-amino-6-chloro-nicotinate A solution of 1.08 g (5.00 mMol) of methyl 6-chloro-5-nitro-nicotinate (see A. H. Berrie, G. T. Newbold, F. S. Spring in J. Chem. Soc., 2590, 1951) in 25 ml of absolute ethanol was mixed successively with 0.53 ml (29 mmol) of water, 3.2 g (57 mMol) of iron powder and 0.030 ml of concentrated hydrochloric acid and heated to boiling for one hour. Then equal quantities of water, iron powder and hydrochloric acid were added and the mixture was heated to boiling for 30 minutes. The precipitate formed on cooling was filtered off and washed with ethanol and the solvent was distilled off in vacuo. Yield: 0.75 g (81percent of theory) of greenish-yellow solid, Rf value: 0.31 (silica gel;ethyl acetate/petroleum ether=1:4) C7 H7 ClN2 O2 (186.60) YEF- Mass spectrum: M+ =186 and 188 (chlorine isotopes).
  • 14
  • [ 59237-53-5 ]
  • [ 104685-75-8 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; REFERENCE EXAMPLE 12 23 Grams of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> was dissolved in 200 ml of dioxane. To this solution was introduced ammonia gas under stirring condition at room temperature. 10 Minutes after the introduction of ammonia gas, the crystals formed in the reaction mixture were collected by filtration. Recrystallized from dimethylformamide (DMF) to yield 18 g of methyl 6-amino-5-nitronicotinate in the form of yellow needle-like crystals. Melting point: 195°-196° C.
With ammonia; In ethanol; at 0℃; for 3h; To <strong>[59237-53-5]methyl 6-chloro-5-nitropyridine-3-carboxylate</strong> (200 mg, 0.92 mmol) was added a 2 M solution of ammonia in EtOH (1.85 ml, 3.69 mmol) at 0 °C. The cooling bath was removed and the mixture was stirred for 3 h. The solvents were removed in vacuo and the crude product taken to the next step. Yellow solid. MS (ESI+) mlz 198 [M+H]+.
  • 15
  • [ 96-35-5 ]
  • [ 59237-53-5 ]
  • [ 924279-03-8 ]
YieldReaction ConditionsOperation in experiment
56% With sodium hydride; In 1,4-dioxane; at 25℃; for 24h; To a solution of methyl beta-chloro-delta-nitro-S-pyridinecarboxylate (2 g, 9.3 mmol) in dioxane (40 mL) were added NaH (0.4 g, 10.2 mmol, 60percent in mineral oil) and methyl EPO <DP n="43"/>hydroxyacetate (0.78 g, 9.3 mmol). After stirring at 25°C for 24 hr, the solution was partitioned between ethyl acetate and water. The aqueous solution was extracted several times with ethyl acetate. The organic fractions were combined, concentrated and purified with column chromatography (silica, 5 -30percent ehtyl acetate in hexane) to provide the title compound as a white solid (1.3 g, 56percent): LC/MS (ES) m/e 271 (M+H)+
  • 16
  • [ 59237-53-5 ]
  • [ 203661-13-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium sulfide nonahydrate; hydrogen sulfide; sodium acetate; sodium sulfate; zinc; In 1,4-dioxane; methanol; water; acetic acid; (a) 5-Amino-6-thioxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester A mixture of sodium sulfide nonahydrate (2.17 g) and sulfur (0.29 g) was heated in boiling water (20 ml) until the solution was homogeneous and added to a solution of 6-chloro-5-nitro-nicotinic acid methyl ester [prepared as described by A. H. Berrie et al. J. Chem. Soc. 2590-2594 (1951)] (3.10 g) in methanol (50 ml). The mixture was boiled for 15 minutes and cooled. The resulting disulfide was collected and washed with water to give a yellow solid (2.46 g). The solid (5 g) in acetic acid (100 ml) and 4M HCl in dioxan (50 ml) was treated with zinc dust (12 g) and the mixture was stirred at room temperature for 30 minutes, filtered and evaporated to dryness. Sodium acetate and sodium sulfate were added and the mixture was extracted with warm chloroform and chromatographed on silica gel, eluding with chloroform then methanol-chloroform to afford a yellow solid (2.3 g). MS (+ve ion electrospray) m/z 185(MH+)
  • 17
  • [ 67-56-1 ]
  • [ 23945-84-8 ]
  • [ 59237-53-5 ]
  • 18
  • [ 623-50-7 ]
  • [ 59237-53-5 ]
  • [ 615568-46-2 ]
YieldReaction ConditionsOperation in experiment
61.7% With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 96h; To a solution of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (3 g, 13.85 mmol) in THF (60 mL) and DMF (30.0 mL) was added ethyl 2-hydroxyacetate (1.573 mL, 16.62 mmol) and potassium carbonate (5.74 g, 41.6 mmol). The reaction was stirred at room temperature for 24 hours. TLC analysis of the reaction mixture indicated partial consumption of starting material. Ethyl 2-hydroxyacetate (1 mL, 10.57 mmol) and potassium carbonate (2 g, 14.5 mmol) were added and the reaction was stirred at room temperature for 72 hours. TLC analysis of the reaction mixture indicated nearly complete consumption of starting material. The reaction mixture was partially concentrated under reduced pressure for removal of THF. The resulting red solution was diluted with H2O (200 mL) and 1N HCl was added to adjust the pH to 7. Theaqueous layer was extracted with EtOAc (3.x.200 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting solid was purified by flash column chromatography using a gradient elution of hexanes with 10-70percent EtOAc to provide methyl 6-(2-ethoxy-2-oxoethoxy)-5-nitronicotinate (2.43 g, 8.55 mmol, 61.7percent yield) as a white solid.1H-NMR (CDCl3) delta 8.95 (d, 1H), 8.88 (d, 1H), 5.12 (s, 2H), 4.23 (q, 2H), 3.97 (s, 3H), 1.27 (t, 3H).
  • 19
  • [ 924-44-7 ]
  • [ 59237-53-5 ]
  • [ 615568-46-2 ]
YieldReaction ConditionsOperation in experiment
A solution of ethyl glyoxalate (2. 80g) in dry dioxan (lOOmL), cooled in ice, was treated with sodium hydride (60percent dispersion in oil; 1.30g) and the mixture was heated at 50°C for 30 minutes and cooled in ice. A solution of 6-chloro-5-nitro-nicotinic acid methyl ester (5.25g) [prepared as described by A. H. Berrie et al. J. Chem. Soc. 2590- 2594 (1951) ] in dioxan (40mL) was added and the solution was stirred at 0°C for 30 minutes and then at room temperature overnight. The reaction mixture was evaporated to dryness, sodium bicarbonate solution was added to pH 7, and the mixture extracted with chloroform, dried (anhydrous sodium sulfate) and evaporated to afford a semi-solid that was chromatographed on silica gel [dichloromethane-hexane (1: 1) then dichloromethane] to afford the product (4.70g). MS (+ve ion electrospray) m/z 285 (MH+).
  • 20
  • [ 67-56-1 ]
  • [ 6635-31-0 ]
  • [ 59237-53-5 ]
YieldReaction ConditionsOperation in experiment
90% DMF (0.15 eq) was added to a solution of beta-hydroxy-S-nitronicotinic acid (1 eq) in SOCl2 (4.7 eq). The mixture was heated at reflux for 8 h then concentrated in vacuo. The residue was taken up in CH2Cl2, cooled to -400C, and MeOH (1.4 eq) added while maintaining the internal temperature below -300C. Aqueous NaHCO3 (1 eq) was added and the mixture allowed to warm to room temperature. The organic phase was separated and concentrated in vacuo. The crude residue was crystallized from EtOH to give methyl 6-chloro-5-nitronicotinate (90 percent yield)
76% A 250 ml. round-bottorned flask was charged with 6-hydroxy-5-nitronicotinicacid (2.72 g, 14.8 mmol) and thionyl chloride (6.6 mL, 90 mmol), purged with N2, DMF(0.11 mL, 1.42 mmol) was added then heated to reflux with stirring overnight. The reaction was cooled to roorn ternperature and concentrated in vacuo. The residue was dissolved in CH2C12 (70 mL), cooled to 0°C, then rnethanol (10 mL, 247 mmol) was added, allowed to gradually warrn to roorn ternperature as bath warrned, and stirredovernight. The reaction mixture was concentrated. The resulting solid was recrystalized frorn hot EtOH, cooled in ice, the solid collected by filtration, washed with cold EtOH, and air dried to afford the product (rnethyl 6-chloro-5-nitronicotinate (2.433 g, 76 percent)) as atan solid: ?H NMR (400 MHz, CDC13) oe 9.18 (d, J=2.0 Hz, 1 H), 8.77 (d, J=2.2 Hz, 1 H), 4.03 (s, 3 H).
75% a)Methyl 6-chloro-5-nitronicotinateN,N'-Dimethylformamide (0.4 mL) was added to a suspension of 6-hydroxy-5-nitronicotinic acid (10.0 g, 50 mmol) in thionyl chloride (50 mL) and the mixture was stirred and heated to 60 °C.After gas evolution had ceased, the mixture was heated to 80 °C and stirred overnight.The mixture was concentrated in vacuo and then co-evaporated with toluene three times.The residue was taken up in dichloromethane (20 mL), cooled to 0 °C and methanol (12 mL) was added dropwise with stirring.The mixture was stirred for 1 hour then evaporated.The residue was partitioned between ethyl acetate and water and the organic layer was separated, dried (MgSO4 and evaporated to give the title compound (8.83 g, 75percent) as a pale yellow solid.LRMS (m/z): 217 (M+1)+.1H NMR delta (300 MHz, CDCl3): 4.03 (s, 3H), 8.77 (d, 1H), 9.18 (d, 1H).
75% 5-(Difluoromethyl)-2-methoxypyridin-3 -amine a) Methyl 6-chloro-5-nitronicotinateLambda/,Lambda/'-Dimethylformamide (0.4 mL) was added to a suspension of 6-hydroxy-5- nitronicotinic acid (10.0 g, 50 mmol) in thionyl chloride (50 mL) and the mixture was stirred and heated to 60 °C. After gas evolution had ceased, the mixture was heated to 80 °C and stirred overnight. The mixture was concentrated in vacuo and then co- evaporated with toluene three times. The residue was taken up in dichloromethane (20 mL), cooled to 0 °C and methanol (12 mL) was added dropwise with stirring. The mixture was stirred for 1 hour then evaporated. The residue was partitioned between ethyl acetate and water and the organic layer was separated, dried (MgS04) and evaporated to give the title compound (8.83 g, 75percent) as a pale yellow solid.LRMS (m/z): 217 (M+1 )+.1H NMR delta (300 MHz, CDCI3): 4.03 (s, 3H), 8.77 (d, 1 H), 9.18 (d, 1 H).
54% To a solution of phosphoryl pentachloride (12.98 g, 62.3 mmol) in phosphoryl chloride (18 mL), was added 3 (4.00 g, 21.7 mmol), and the mixture was stirred for 3 h at 100 oC equipped with condenser. Then, the excess amount of phosphoryl chloride was removed in vacuo at 50 oC, and the residue was dissolved in MeOH (30 mL) at 0 oC and further stirred for 30 min. Excess amount of MeOH was removed in vacuo and the residue was dissolved in AcOEt. This organic layer was washed with water, brine and dried over anhydrous Na2SO4. After the solvent was removed in vacuo, the resultant residue was purified by column chromatography on silica gel using hexane/AcOEt (6:1) as an eluant to give 4 as pale yellow needles (2.54 g, 54percent); 1H NMR (300 MHz, CD3OD) 4.00 (s, 3H), 8.52 (d, J = 2.1Hz, 1H), 9.14 (d, J = 2.1 Hz, 1H); HRMS (ES+): m/z 217.0006 (M+H+) (calcd for C7H6N2O4Cl: 217.0016).
52% A. 6-Chloro-5-nitro-nicotinic acid methyl ester; To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicotinic acid in thionyl chloride (240 ml) is added DMF (2 ml). This mixture is stirred at 60°C and after gassing stops it is stirred at 80°C for further 18 h. The thionyl chloride is removed under vacuo and the residue is coevaporated with toluene three times. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the titled compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol).
18.2 g Compound 2 (20.0 g) and N,N-dimethylformamide (8.44 mL, 0.109 mmol) were added to a 500 mL recovery flask in an argon gas stream, and thionyl chloride (158.3 mL, 2.18 mmol) was added while cooling by ice bath. After the entire amount of thionyl chloride had been added, the flask was returned to room temperature. It was then gradually heated using an oil bath, and stirring was conducted for 16 hours at 80° C. After stopping heating and allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure. Dichloromethane (50 mL) was added to the residue obtained, which was again concentrated, and the remaining thionyl chloride was distilled off azeotropically. After concentration, the residue obtained was cooled by an ice bath, and methanol (50 mL) was added. Compound 3 (18.2 g, 0.084 mmol) was obtained by concentration and drying under reduced pressure. 1H NMR (300 MHz, CD3OD) 4.00 (s, 3H), 8.52 (d, J=2.1 Hz, 1H), 9.14 (d, J=2.1 Hz, 1H); HRMS (ES+): m/z 217.0006 (M+H)+ (calcd for C7H8N2O4Cl: 217.0016).

  • 21
  • [ 5473-12-1 ]
  • [ 59237-53-5 ]
  • [ 1236119-07-5 ]
YieldReaction ConditionsOperation in experiment
99% at 20 - 90℃;Inert atmosphere; Neat (no solvent); Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(methylamino)acetate (1.9 g, 18.47 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one hour and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified using flash column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield 2.60 g (99percent yield) of the title compound as a yellow oil. [M+H] calc'd for C11H13N3O6, 284; found, 284.
  • 22
  • [ 288-32-4 ]
  • [ 59237-53-5 ]
  • [ 1236119-42-8 ]
YieldReaction ConditionsOperation in experiment
Methyl 6-chloro-5-nitronicotinate (2.17 g, 10.0 mmol) was dissolved in ethyl acetate (55 mL) and imidazole (4.09 g, 60 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and treated with 5 nCl2-2H2O (13.5 g, 60.0 mmol). It was heated to 70° C. for 2 h, diluted with potassium carbonate (sat. aq.) and extracted with ethyl acetate (5.x.20 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a crude yellow solid, which was used in the next step without further purification. [M+H] calc'd for C10H10N4O2, 219; found, 219.
  • 23
  • [ 59237-53-5 ]
  • [ 69684-69-1 ]
  • [ 1236119-53-1 ]
YieldReaction ConditionsOperation in experiment
92% (S)-methyl azetidine-2-carboxylate hydrochloride (1 g, 6.60 mmol) was diluted with Tetrahydrofuran (Volume: 20 ml) and treated with TRIETHYLAMINE (0.919 ml, 6.60 mmol). The reaction mixture was stirred vigorously and sonicated periodically, until a fine suspension resulted. This was stirred for 1 h and filtered through a small plug of celite. The plug was washed well with THF (20 mL) and the combined filtrate and washes were treated with <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (0.714 g, 3.30 mmol). The reaction mixture was concentrated in vacuo and heated briefly (5 min) to 80° C. LCMS showed complete conversion. The reaction mixture was diluted with DCM (10 mL) and purified using flash column chromatography on silica gel (80 g SiO2, 20-30percent ethyl acetate in hexanes) to afford the title compound (S)-methyl 6-(2-(methoxycarbonyl)azetidin-1-yl)-5-nitronicotinate (0.90 g, 3.05 mmol, 92percent yield) as a yellow oil. [M+H] calc'd for C12H13N3O6, 295; found, 295.
  • 24
  • [ 126264-49-1 ]
  • [ 59237-53-5 ]
  • C13H15N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In tetrahydrofuran; for 3h;Inert atmosphere; Reflux; To a suspension of methyl morpholine-3-carboxylate (2.0 g, 13.78 mmol) in THF was added methyl <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (2.71 g, 12.53 mmol) and potassium carbonate (5.19 g, 37.6 mmol). The suspension was heated to reflux for 3 hours. The crude orange solution was allowed to cool to RT and filtered through a pad of celite which was washed with DCM (50 mL) and transferred to a bomb hydroginator. To the solution was added triphenyl phosphite (0.039 ml, 0.125 mmol), platinum (5percent, 0.489 g, 0.125 mmol), and ammonium metavanadate (0.117 g, 1.0 mmol). The vessel was sealed and pressurized to 140 psi with stirring for 24 h at room temperature. The vessel was depressurized and the mixture was diluted with DCM (100 mL) and refluxed for 30 minutes. The hot mixture was filtered through celite and concentrated to yield 1.98 g (60percent) of the product as a white solid. [M+H] calc'd for C12H13N3O4, 264; found, 264.
  • 25
  • [ 67-56-1 ]
  • [ 1193-62-0 ]
  • [ 59237-53-5 ]
  • [ 1236119-77-9 ]
YieldReaction ConditionsOperation in experiment
92% Methyl 1H-pyrrole-2-carboxylate (5.78 g, 46.2 mmol) was dissolved in DMSO and cooled to 10° C. NaH was added in two portions over 5 min. The reaction mixture was stirred at 10° C. for 10 min and <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (5 g, 23.09 mmol) in DMSO (10 mL) was added slowly over 3 min. The red reaction mixture was allowed to warm to room temperature and stirred overnight. It was cooled to 0° C. and quenched with water (12 mL) and diluted with brine (50 mL). The mixture was washed with EtOAc (2.x.25 mL) and the aqueous layer was acidified to pH=2 with 4.5 N HCl. It was extracted with EtOAc (1.x.100 mL) and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford a yellow solid, which was dissolved in MeOH (100 mL) and cooled to 0° C. Thionyl chloride (45 mL, 617 mmol) was added slowly over 5 min. The reaction mixture was stirred at 0° C. for 1 h and then at room temperature overnight. It was concentrated in vacuo and the resulting solid was triturated with ethyl acetate (300 mL). The solid was filtered off and the filtrate was concentrated in vacuo. then washed with ethyl ether to afford methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate (5.04 g, 16.51 mmol, 92percent yield) as a yellow solid, [M+H] calc'd for C13H11N3O6, 306; found, 306.
  • 26
  • [ 59237-53-5 ]
  • [ 35677-83-9 ]
  • [ 1236119-48-4 ]
YieldReaction ConditionsOperation in experiment
98% at 90℃; for 1h;Inert atmosphere; Neat (no solvent); Methyl 6-chloro-5-nitronicotinate (2.333 g, 10.77 mmol) was added to (S)-methyl piperidine-2-carboxylate (2.93 g, 20.46 mmol) neat while stirring. The reaction was stirred 1 h at 90° C., cooled to room temperature and taken up in ethyl acetate (10 mL). The mixture was purified by SiO2 (330 g, 20-30percent EA in Hexanes) to yield 3.4 g (98percent) of the title compound as a yellow oil. [M+H] calc'd for C14H17N3O6, 324; found, 324.
  • 27
  • [ 59237-53-5 ]
  • [ 128019-59-0 ]
  • [ 1236119-21-3 ]
YieldReaction ConditionsOperation in experiment
96% To a suspension of 4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1169 mg, 5.08 mmol) in THF (46 mL) was added <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (1000 mg, 4.62 mmol) and K2CO3 (638 mg, 4.62 mmol). The suspension was heated to reflux for 2 hours, cooled to room temperature, and filtered through a pad of celite. The celite was washed with DCM (50 mL) and the organic portions were combined. The solution was charged into a bomb hydroginator, then treated with triphenyl phosphite (0.015 ml, 0.048 mmol), ammonium vanadate (44 mg, 0.380 mmol), and platinum (1.853 g, 0.475 mmol). The reaction was sealed and pressurized with hydrogen gas (150 psi) overnight. The reaction was then diluted with DCM (100 mL) and heated to reflux for 1 hr. The hot mixture was filtered through celite, washed with DCM (50 mL), and concentrated to 1.65 g (96percent) of the title compound as an off-white solid. [M+H] calc'd for C17H22N4O5, 363; found, 363.
  • 28
  • [ 59237-53-5 ]
  • [ 2577-48-2 ]
  • [ 1236119-32-6 ]
YieldReaction ConditionsOperation in experiment
94% at 90℃; for 0.166667h;Inert atmosphere; (S)-Methyl pyrrolidine-2-carboxylate (6.56 g, 50.8 mmol) was added to <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (5.00 g, 23.1 mmol) and the reaction mixture was stirred at 90° C. for 10 min (exothermic reaction). It as cooled to room temperature, diluted with EtOAc (10 mL) and purified using flash column chromatography on silica gel (20-30percent EtOAc in hexanes) to afford the title compound as a yellow oil (6.70 g, 94percent). [M+H] calc'd for C13H15N3O6, 310; found, 310.
  • 29
  • [ 59237-53-5 ]
  • [ 35677-83-9 ]
  • [ 1236119-47-3 ]
YieldReaction ConditionsOperation in experiment
99% at 20 - 90℃;Inert atmosphere; Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl piperidine-2-carboxylate (5.2 g, 36.92 mmol) while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (2.95 g, 99percent yield) as a yellow oil. [M+H] calc'd for C14H17N3O6, 324; found, 324.
  • 30
  • [ 59237-53-5 ]
  • [ 53386-64-4 ]
  • [ 1236119-50-8 ]
YieldReaction ConditionsOperation in experiment
90% at 20 - 90℃;Neat (no solvent); Inert atmosphere; Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(benzylamino)acetate (6.0 g, 31.05 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (3.10 g, 90percent yield) as a yellow oil. [M+H] calc'd for C18H19N3O6, 374; found, 374.
  • 31
  • [ 59237-53-5 ]
  • [ 65527-54-0 ]
  • [ 1236119-13-3 ]
YieldReaction ConditionsOperation in experiment
52% To a suspension of (R)-thiomorpholine-3-carboxylic acid (1.009 g, 6.86 mmol) in THF was added <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (1.35 g, 6.23 mmol) and potassium carbonate (2.58 g, 18.70 mmol). The suspension was heated to reflux for 3 hours. The crude orange solution was allowed to cool to RT and filtered through a pad of celite which was washed with DCM (50 mL), and transferred to a bomb hydroginator. To the solution was added triphenyl phosphite (0.019 ml, 0.061 mmol), platinum (0.238 g, 0.061 mmol), and ammonium metavanadate. The vessel was sealed and pressurized to 140 psi with stirring for 24 h at room temperature. The vessel was depressurized and the mixture was diluted with DCM (100 mL) and refluxed for 30 minutes. The hot mixture was filtered through celite and concentrated to yield 887 mg (52percent) of the product as a white solid. [M+H] calc'd for C12H13N3O3S, 280; found, 280.
  • 32
  • [ 59237-53-5 ]
  • [ 58729-31-0 ]
  • [ 1236119-51-9 ]
YieldReaction ConditionsOperation in experiment
95% at 20 - 90℃;Neat (no solvent); Inert atmosphere; Methyl 6-chloro-5-nitronicotinate (1.1 g, 5.10 mmol) was added to ethyl thiomorpholine-3-carboxylate (2.0 g, 11.41 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one hour and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (1.71 g, 95percent) as a yellow oil. [M+H] calc'd for C15H18N2O6S, 356; found, 356.
  • 33
  • [ 59237-53-5 ]
  • [ 754177-25-8 ]
  • [ 1236119-54-2 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Tert-butyl 2-(pyrrolidin-2-yl)acetate (1.00 g, 5.40 mmol) was added to a solution of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (1.169 g, 5.40 mmol) in THF (Volume: 10 ml). The reaction mixture was stirred at rt for 1 h and K2CO3 (0.760 g, 5.50 mmol) was added. The reaction mixture was stirred for 2 h and triethylamine (0.379 ml, 2.70 mmol) was added. The mixture was stirred for 1 h, filtered and concentrated in vacuo. Flash column chromatography on silica gel (120 g SiO2, hexanes:ethyl acetate 9:1) afforded methyl 6-(2-(2-tert-butoxy-2-oxoethyl)pyrrolidin-1-yl)-5-nitronicotinate (1.79 g, 4.90 mmol, 91percent yield) as a yellow oil. [M+H] calc'd for C17H23N3O6, 365; found, 365.
  • 34
  • [ 59237-53-5 ]
  • [ 207916-93-6 ]
  • [ 1236119-37-1 ]
YieldReaction ConditionsOperation in experiment
42% at 90℃; for 20h;Inert atmosphere; closed vial; (S)-ethyl 2-(isopropylamino)propanoate (2.83 g, 17.8 mmol) was added to <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (1.72 g, 7.94 mmol) and the reaction mixture was stirred in a closed vial at 90° C. for 20 h. It was cooled and diluted with EtOAc (25 mL). The resulting precipitate was filtered off, the filtrate was concentrated in vacuo and purified using flash column chromatography on silica gel (220 g SiO2, hexanes:ethyl acetate 4:1) to afford the title compound as yellow oil (1.12 g, 42percent). 1H NMR (400 MHz, CHLOROFORM-d) delta (ppm): 1.18 (t, J=7.07 Hz, 3H) 1.30 (d, J=6.32 Hz, 3H) 1.36 (d, J=6.57 Hz, 3H) 1.66 (d, J=6.82 Hz, 3H) 3.48-3.62 (m, 1H) 3.90 (s, 3H) 4.03 (q, J=6.65 Hz, 1H) 4.06-4.21 (m, 2H) 8.54 (d, J=2.02 Hz, 1H) 8.70 (d, J=2.02 Hz, 1H); [M+H] calc'd for C15H21N3O6, 340; found, 340.
  • 35
  • [ 59237-53-5 ]
  • [ 1236119-39-3 ]
  • [ 1236119-40-6 ]
YieldReaction ConditionsOperation in experiment
66% at 90℃; for 1h;Inert atmosphere; closed vial; (S)-methyl 2-(ethylamino)propanoate (1.83 g, 14.0 mmol) was added to <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> (1.30 g, 6.00 mmol) and the reaction mixture was stirred in a closed vial at 90 C. for 1 h. It was cooled and diluted with EtOAc (25 mL). The resulting precipitate was filtered off, the filtrate was concentrated in vacuo and purified using flash column chromatography on silica gel (220 g SiO2, ethyl acetate in hexanes 0-50%) to afford the title compound as a yellow oil (1.23 g, 66%). [M+H] calc'd for C14H19N3O6, 326; found, 326.
 

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Technical Information

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[ 59237-53-5 ]

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