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Chemical Structure| 5334-40-7
Chemical Structure| 5334-40-7
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Product Details of [ 5334-40-7 ]

CAS No. :5334-40-7 MDL No. :MFCD00090899
Formula : C4H3N3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZMAXXOYJWZZQBK-UHFFFAOYSA-N
M.W : 157.08 Pubchem ID :219739
Synonyms :

Calculated chemistry of [ 5334-40-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.37
TPSA : 111.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.56
Log Po/w (XLOGP3) : -0.1
Log Po/w (WLOGP) : 0.02
Log Po/w (MLOGP) : -1.78
Log Po/w (SILICOS-IT) : -1.56
Consensus Log Po/w : -0.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.96
Solubility : 17.4 mg/ml ; 0.111 mol/l
Class : Very soluble
Log S (Ali) : -1.8
Solubility : 2.52 mg/ml ; 0.016 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.02
Solubility : 166.0 mg/ml ; 1.05 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 5334-40-7 ]

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

Application In Synthesis of [ 5334-40-7 ]

* 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.

  • Upstream synthesis route of [ 5334-40-7 ]
  • Downstream synthetic route of [ 5334-40-7 ]

[ 5334-40-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 5334-40-7 ]
  • [ 116008-52-7 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 2418,2422
  • 2
  • [ 1453-58-3 ]
  • [ 5334-40-7 ]
Reference: [1] Russian Chemical Bulletin, 1993, vol. 42, # 11, p. 1861 - 1864[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993, # 11, p. 1945 - 1948
  • 3
  • [ 67-56-1 ]
  • [ 5334-40-7 ]
  • [ 138786-86-4 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: at 20℃; for 16 h;
Stage #2: With water; sodium hydrogencarbonate In methanol; ethyl acetate
Reference Example 1
Methyl 4-nitro-1H-pyrazole-3-carboxylate
Acetyl chloride (9 mL) was added dropwise to methanol (90 mL), 4-nitro-1H-pyrazole-3-carboxylic acid (9.00 g, 57.3 mmol) was added to the mixture.
The mixture was stirred at room temperature for 16 hr, and concentrated under reduced pressure.
Methanol was added to the residue, and the mixture was concentrated under reduced pressure, the operation was twice repeated.
The residue was diluted with methanol and ethyl acetate.
5percent sodium hydrogencarbonate aqueous solution was added, and the pH was adjusted to 8-9.
The mixture was extracted with ethyl acetate.
The extract was washed with water, brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (9.83 g, yield 100percent).
1H-NMR (DMSO-d6, 200 MHz): δ 3.98 (3H, s), 8.28 (1H, s).
100%
Stage #2: With sodium hydrogencarbonate In methanol; water; ethyl acetate
Acetyl chloride (9 mL) was added dropwise to methanol (90 mL), 4-nitro-1H-pyrazole-3-carboxylic acid (9.00 g, 57.3 mmol) was added to the mixture. The mixture was stirred at room temperature for 16 hr, and concentrated under reduced pressure. Methanol was added to the residue, and the mixture was concentrated under reduced pressure, the operation was twice repeated. The residue was diluted with methanol and ethyl acetate. 5percent sodium hydrogencarbonate aqueous solution was added, and the pH was adjusted to 8 - 9. The mixture was extracted with ethyl acetate. The extract was washed with water, brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (9.83 g, yield 100percent). 1H-NMR (DMSO-d6, 200 MHz):δ 3.98(3H, s), 8.28(1H, s).
100% at 20℃; Cooling with ice Dissolve 4-nitro-1H-pyrazole-3-carboxylic acid in methanol (50 ml) and add thionyl chloride (2.5 ml) dropwise on an ice bath. The reaction is allowed to proceed overnight at room temperature. Concentration under reduced pressure gave 4.36 g of a white solid. Yield: 100percent
99.5% at 0 - 22℃; for 48 h; EXAMPLE 1 Synthesis of the methanesulphonic acid salt of 4-{2,6-dichloro-benzoylaminoHH- pyrazole-3-carboxylic acid piperidin-4-ylamide and crystals thereofThe methane sulphonic acid salt of 4-(2,6-dichloro-benzoylamino)-lH-pyrazole-3- carboxylic acid piperidin-4-ylamide may be prepared by the synthetic route shown in the Scheme below. EPO <DP n="73"/>SOCI2, MeOH Stage 1 4H3N3O4 5H5N3O4 Stage 2 C5H7 3O2 FW: 157.09 FW: 171.11 FW: 141.13C12H9CI2N3O3 C11H7CI2N3O3 FW: 314.13 FW: 300.10Stage 5Stage 1 : Preparation of 4-nitro-li7-pyrazole-3-carboxylic acid methyl esterC4H3N3O4 C5H5N3O4 FW: 157.09 FW: 171.11 EPO <DP n="74"/>A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-l/7-pyrazole-3-carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 0C, thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 °C overnight, after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 0C, the residue treated with toluene and re-concentrated (3x 2.250 L, 3x 2vol) under reduced pressure at 40 to 45 0C to give 4-nitro-l/f-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5percent).; EXAMPLE I lPreparation of 4-(2,6-dichloro-benzoylamino)-lH-pyrazole-3-carboxylic acid piperidin-4-ylamide hydrochlorideHA. Synthesis of 4-nitro-lH-pyrazole-3-carboxylic acid methyl esterThionyl chloride (2.90 ml, 39.8 mmol) is slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in methanol (100 ml) at ambient temperature and the mixture is stirred for 48 hours. The mixture is reduced in EPO <DP n="98"/>vacuo and dried through azeotrope with toluene to afford the 4-nitro-lH-pyrazole- 3-carboxylic acid methyl ester.
99.5% at 0 - 22℃; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-1H-pyrazole-3- carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 °C, thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 °C overnight, after which time 1H NMR analysis (dβ- DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 °C, the residue treated with toluene and re-concentrated (3x 2.250 L, 3x 2vol) under reduced pressure at 40 to 45 °C to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5percent).
99.5% at 0 - 22℃; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-1H-pyrazole-3- carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 °C, thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 °C overnight, after which time 1H NMR analysis (dβ- DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 °C, the residue treated with toluene and re-concentrated (3x 2.250 L, 3x 2vol) under reduced pressure at 40 to 45 °C to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5percent).
99.5% at 0 - 22℃; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4- nitro-1/-/-pyrazole-3-carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8 950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to O to 5 0C, thionyl chloride <n="161"/>(0.581 L1 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 0C overnight, after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 0C, the residue treated with toluene and re-concentrated (3x 2.250 L, 3x 2vol) under reduced pressure at 40 to 45 0C to give 4-nitro-1 H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5percent).
99% at 0 - 70℃; for 5 h; To a solution of 4-nitro-3-pyrazolecarboxylic acid (3.14 g,20.0 mmol) in MeOH (50 mL) was slowly added thionyl chloride(7.3 mL, 0.1 mol) at 0 °C. After the completion of the addition, thetemperature of the reaction mixture increased to 70 °C and stirredfor 5 h. Methanol was removed in vacuo, and the resulting residuewas poured into ice water and extracted with EtOAc. The organiclayer was washed with 10percent NaHCO3 solution, brine and dried overNa2SO4. The resulting reaction mixture concentrated in vacuo toafford 1 as a white solid (3.37 g, 99percent). 1H NMR (400 MHz, DMSO-d6)δ 8.93 (s, 1H), 3.89 (s, 3H); 13C NMR (100 MHz, DMSO-d6)δ 161.4,138.0, 133.7, 132.0, 53.3.
99.8% at 0 - 25℃; for 16 - 24 h; Industry scale Stage 1: Preparation of 4-nitro-lH-pyrazole-3-carboxylic acid methyl esterC4H3N3O4 C5H5N3O4FW: 157.09 FW: 171.114-Nitro-lH-pyrazole-3-carboxylic acid (1.350Kg, 8.59 MoI, 1.0 wt) and methanol (10.80L, 8.0 vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0 to 5°C under nitrogen and thionyl chloride (0.702L, 9.62 MoI, 0.52 vol) added at this temperature. The mixture was warmed to 15 to 250C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6-DMSO). The mixture was concentrated under vacuum at 35 to 450C and toluene (2.70L, 2.0 vol) charged to the residue and removed under vacuum at 35 to 45°C. The toluene azeotrope was repeated twice using toluene (2.70L, 2.0 vol) to give 4-nitro-lH-pyrazole-3-carboxylic acid methyl <n="72"/>ester [1.467Kg, 99.8percentth, 108.7percent w/w, 1H NMR Cd6-DMSO) concordant with structure, no entrained solvent] as an off-white solid.
98.3% at 0 - 25℃; for 16 - 24 h; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-17f-pyrazole-3-carboxylic acid (1.117Kg, 7.11mol, lwt) and methanol (8.950L5 8vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 50C, thionyl chloride (0.581L, 8.0mol, 0.52vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 220C overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 450C, the residue treated with toluene and re-concentrated (3x 2.250L, 3x 2vol) under reduced pressure at 40 to 450C to give 4-nitro-l//-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210Kg, 99.5percentth).; 4-Nitro-lH-pyrazole-3-carboxylic acid (1.00kg, 6.37mol, l.Owt) and methanol (8.00L, 8.0vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0 to 5°C under nitrogen and thionyl chloride (0.52L, 7.12mol, 0.52vol) was added at this temperature. The mixture was warmed to 15 to 25°C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6-DMSO). The mixture was concentrated under vacuum at 35 to 45°C. Toluene (2.00L, 2.0vol) was charged to the residue and removed under vacuum at 35 to 450C. The azeotrope was repeated twice using toluene (2.00L, 2.0vol) to give 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (1.071Kg, 98.3percent) as an off white solid.
98.3% at 0 - 25℃; for 16 - 48 h; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with A- nitro-1H-pyrazole-3-carboxylic acid (1.117Kg, 7.11mol, 1wt) and methanol (8.950L, δvol). The reaction mixture was stirred under nitrogen, cooled to 0 to 50C, thionyl chloride (0.581 L, δ.Omol, 0.52vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22°C overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 450C, the residue treated with toluene and re-concentrated (3x 2.250L, 3x 2vol) under reduced pressure at 40 to 450C to give 4-nitro-1 /-/-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210Kg, 99.5percentth).4-Nitro-1H-pyrazole-3-carboxylic acid (1.00kg, 6.37mol, 1.0wt) and methanol (8.00L, δ.Ovol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0 to 5°C under nitrogen and thionyl chloride (0.52L, 7.12mol, 0.52vol) was added at this temperature. The mixture was warmed to 15 to 25°C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6- DMSO). The mixture was concentrated under vacuum at 35 to 45°C. Toluene (2.00L, 2.0vol) was charged to the residue and removed under vacuum at 35 to 450C. The azeotrope was repeated twice using toluene (2.00L, 2.0vol) to give 4-nitro-1 H-pyrazole-3- carboxylic acid methyl ester (1.071 Kg, 98.3percent) as an off white solid.Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in MeOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1 H-pyrazole-3-carboxylic acid methyl ester as a white solid.1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, 1 H), 8.9 (s, 1 H), 3.9 (s, 3H)4-Nitro-1H-pyrazole-3-carboxylic acid (1.350Kg, 8.59 MoI, 1.0 wt) and methanol (10.80L, 8.0 vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to O to 50C under nitrogen and thionyl chloride (0.702L, 9.62 MoI, 0.52 vol) added at this temperature. The mixture was warmed to 15 to 25°C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6- DMSO). The mixture was concentrated under vacuum at 35 to 45°C and toluene (2.70L, 2.0 vol) charged to the residue and removed under vacuum at 35 to 45°C. The toluene azeotrope was repeated twice using toluene (2.70L, 2.0 vol) to give 4-nitro-1 H-pyrazole-3- carboxylic acid methyl ester [1.467Kg, 99.8percentth, 108.7percent w/w, 1H NMR (d6-DMSO) concordant with structure, no entrained solvent] as an off-white solid.
98.3% at 0 - 25℃; for 16 - 24 h; Stage 4: Synthesis of 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with 4- nitro-lH-pyrazole-3-carboxylic acid (1.117Kg, 7.11mol, lwt) and methanol (8.950L, 8vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 50C, thionyl chloride (0.581L, 8.0mol, 0.52vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22°C overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 450C, the residue treated with toluene and re-concentrated (3x 2.250L, 3x 2vol) under reduced pressure at 40 to 45°C to give 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210Kg, 99.5percentth).; Stage 4: Preparation of 4-nitro-lH-pyrazole-3-carboxylic acid methyl; esterC4H3N3O4 C5H5N3O4FW: 157.09 FW: 171.114-Nitro-lH-pyrazole-3-carboxylic acid (1.00kg, 6.37mol, l.Owt) and methanol (8.00L, 8.0vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0 to 5°C under nitrogen and thionyl chloride (0.52L, 7.12mol, 0.52vol) was added at this temperature. The mixture was warmed to 15 to 25°C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (dβ-DMSO). The mixture was concentrated under vacuum at 35 to 45°C. Toluene (2.00L, 2.0vol) was charged to the residue and removed under vacuum at 35 to 45°C. The azeotrope was repeated twice using toluene (2.00L, 2.0vol) to give 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (1.071Kg, 98.3percent) as an off white solid.
98% at 20℃; for 24 h; Step 1. Synthesis of methyl 4-nitro-1 /-/-pyrazole-3-carboxylate (C29). Fuming sulfuric acid (4 mL) was added to a solution of 4-nitro-1 /-/-pyrazole-3-carboxylic acid (16.0 g, 102 mmol) in methanol (200 mL), and the reaction was stirred at RT for 24 hours. The reaction mixture was concentrated, and the resulting solid was partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, providing C29 as a white solid. Yield: 17.1 g, 99.9 mmol, 98percent. LCMS m/z 170.0 (M-1 ). H NMR (400 MHz, CDCI3) δ 4.05 (s, 3H), 8.40 (s, 1 H).
96.9% at 25℃; for 16 h; 4-nitro-lH-pyrazole-3-carboxylic acid (30.0 g, 191.0 mmol) was dissolved in methanol (300 mL)Sulfoxide (34.1 g, 286.5 mol) was added,25 ° C for 16 hours.The reaction solution was concentrated in vacuo,Saturated sodium bicarbonate solution (400 mL) was added,Ethyl acetate extraction (500 mL x 2),Organic synthesis,Saturated brine (300 mL),Dried over anhydrous sodium sulfate,The product was concentrated in vacuo (31.7 g, 96.9percent yield).
95.8% at 20℃; Example 43trans-5-[3-oxospiro[6-azaisobenzofuran-1(3H),1'-cyclohexan]-4'-yl]-2-phenyl-2,4-dihydroimidazo[4,5-c]pyrazole(1) Preparation of methyl 4-nitro-1H-pyrazole-3-carboxylate Thionyl chloride (5.1 mL, 70.0 mmol) was added portionwise to a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (10.0g, 63.7 mmol) in methanol (100 mL). After the mixture was stirred overnight at room temperature, the solvent was evaporated in vacuo. After the residue was dissolved in ethyl acetate, the solution was washed with water and saturated aqueous brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title compound (10.43 g, 95.8 percent).
92.1% at 25 - 60℃; for 4 h; The 4-nitro-1H-pyrazole-3-carboxylic acid (20.0 g, 0.127 mmol) was dissolved in methanol (100 mL) and thionyl chloride (18.1 g, 0.152 mmol) was added , allowed to react for 2 hours at 25 ° C. , then heated to 60 ° C, and allowed to react for 2 hours. The reaction was concentrated in vacuo and methyl tert-butyl ether (80 mL) was added and filtered to give a white solid which was dried in vacuo to give the product (20.0 g, 92.1percent yield).
91% at 0 - 20℃; for 2 h; Reference Example 18
Methyl 4-nitro-1H-pyrazole-3-carboxylate
To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (10.0 g, 63.7 mmol) in methanol (100 mL), thionyl chloride (5.1 mL, 70.0 mmol) was added dropwise at 0° C., and the mixture was stirred at room temperature for 2 hr.
The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in ethyl acetate.
This solution was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure to give the title compound (9.9 g, yield 91percent).
1H-NMR (CDCl3): δ 4.06 (3H, s), 8.51 (1H, s).
91%
Stage #1: With thionyl chloride In methanol at 20℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (10.0 g, 63.7 mmol) in methanol (100 mL), thionyl chloride (5.1 mL, 70.0 mmol) was added dropwise at 0°C, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in ethyl acetate. This solution was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (9.9 g, yield 91percent). 1H-NMR (CDCl3) :δ 4.06(3H, s), 8.51(1H, s).
91.7% at 20℃; for 16 h; 4-Nitro-1H-pyrazole-3-carboxylic acid (20 g, 127.3 mmol) was dissolved in methanol (200 mL) and thionyl chloride (22.7 g, 190.8 mmol) was added and reacted at 20 ° C for 16 hours. The reaction was completed and concentrated. Methyl tert-butyl ether (200 mL) was added and filtered to give 20 g of the title product in 91.7percent yield.
89% at 65℃; for 16 h; To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (5 g, 31.8 mmol) in dry MeOH (60 ml) was added freshly crystallized p-toluenesulphonic acid monohydrate (300 mg, 1.6 mmol). The reaction mixture was heated at 65° C. for 16 hrs. MeOH was removed in vacuo. The residue was taken up with saturated aqueous NaHCO3 solution (15 ml) and extracted with EtOAc. The combined organic layers were washed with water, and then with brine, dried (Na2SO4), filtered, and evaporated. The crude product was purified by column chromatography over silica gel using 30percent EtOAc /hexane) to provide the title compound as white solid (4.85 g, 89percent).
89%
Stage #1: at 65℃; for 16 h; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In water
To a solution of 4-nitro-lH-pyrazole-3-carboxylic acid (5 g, 31.8 mmol) in dry MeOH (60ml) was added freshly crystallized p-toluenesulphonic acid monohydrate (300 mg, 1.6 mmol). The reaction mixture was heated at 65 °C for 16 hrs. MeOH was removed in vacuo. The residue was taken up with saturated aqueous NaHC03 solution (15 ml) and extracted with EtOAc. The combined organic layers were washed with water, and then with brine, dried (Na2S04), filtered, and evaporated. The crude product was purified by column chromatography over silica gel using 30percentEtOAc/hexane) to provide the title compound as white solid (4.85 g, 89percent).
86% for 3.5 h; Heating / reflux Reference Example 1 Methyl 4-nitro-1H-pyrazole-3-carboxylate Conc. sulfuric acid(8.2 mL) was added to 4-nitro-1H-pyrazole-3-carboxylic acid(163.8 g) dissolved in methanol(1.64 L) under argon atmosphere and the mixture was heated under reflux for 3.5 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure and the resulted residue was triturated in diisopropyl ether. The precipitate was collected by filtration to give the titled compound(153.2 g, 86percent yield) as a colorless crystalline. mp.115-117°C, MS(ESI)m/z:170 [M-H]-.
72.7% at 0 - 20℃; for 16 h; Acetyl chloride (6.34 ml, 89 mmol) was added to the mixture of 4-nitro-1H-pyrazole-3-carboxylic acid (2, 7 g, 44.6 mmol) in MeOH (223 ml) at 0 °C.
The mixture was stirred at rt for 16 h.
After concentrated in vacuo, the residue was azeotroped with MeOH two times.
The residue was diluted with MeOH and EtOAc, and the mixture was adjusted to a pH of approx. 9 with satd NaHCO3 aq.
The mixture was extracted with EtOAc.
The organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated to give the compound 12 (5.545 g, 32.4 mmol, 72.7percent) as a white powder. 1H NMR (DMSO-d6) δ 14.39 (br s, 1H), 8.99 (s, 1H), 3.89 (s, 3H); 13C NMR (DMSO-d6) δ 161.1, 138.1, 133.2, 130.9, 52.8; HRMS (ESI) m/z: [M−H] calcd for C5H4N3O4: 170.0207, found: 170.0200.
48.8% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 18 h; A mixture [OF 4-NITRO-LH-PYRAZOLE-3-CARBOXYLIC] acid (2.0 g, 12.7 mmol) in dichloromethane at [25 oC] was treated with 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (2.68 g, 14.0 mmol), methanol (8.2 mL), and 4- dimethylaminopyridine (155 mg, 1.27 mmol). The reaction was stirred at [25 oC] for 18 h. At this time, the reaction was diluted with dichloromethane and was washed with a 1N aqueous hydrochloric acid solution (1 x 50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230-400 mesh, 45: 55 ethyl acetate/petroleum ether) afforded 4-nitro- [1H-PYRAZOLE-3-CARBOXYLIC] acid methyl ester (1.06 g, 48.8percent) as a white solid: LR-MS for [C5H5N304] [(M-H) + AT M/Z] = 170.

Reference: [1] Patent: US2009/156582, 2009, A1, . Location in patent: Page/Page column 28
[2] Patent: EP1847531, 2007, A1, . Location in patent: Page/Page column 40
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 979 - 984
[4] Patent: CN107652293, 2018, A, . Location in patent: Paragraph 0099; 0100; 0101
[5] Patent: WO2006/77426, 2006, A2, . Location in patent: Page/Page column 71-73; 96-97
[6] Patent: WO2006/77425, 2006, A1, . Location in patent: Page/Page column 210-211
[7] Patent: WO2006/77424, 2006, A1, . Location in patent: Page/Page column 189-190
[8] Patent: WO2006/77428, 2006, A1, . Location in patent: Page/Page column 189-190
[9] Patent: WO2008/7113, 2008, A2, . Location in patent: Page/Page column 159-160
[10] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7536 - 7549
[11] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 551 - 564
[12] Patent: WO2007/129066, 2007, A1, . Location in patent: Page/Page column 29; 70-71
[13] Patent: WO2006/70195, 2006, A1, . Location in patent: Page/Page column 181; 188
[14] Patent: WO2008/1101, 2008, A2, . Location in patent: Page/Page column 291; 297; 333; 358; 362
[15] Patent: WO2007/77435, 2007, A1, . Location in patent: Page/Page column 237; 243
[16] Patent: WO2012/73143, 2012, A1, . Location in patent: Page/Page column 51
[17] Russian Chemical Bulletin, 1993, vol. 42, # 11, p. 1861 - 1864[18] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993, # 11, p. 1945 - 1948
[19] Patent: CN107226807, 2017, A, . Location in patent: Paragraph 0239-0241; 0305-0307
[20] Patent: EP1566384, 2005, A1, . Location in patent: Page/Page column 50
[21] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 4, p. 1169 - 1172
[22] Patent: CN107286169, 2017, A, . Location in patent: Paragraph 0155-0157
[23] Patent: US2009/156582, 2009, A1, . Location in patent: Page/Page column 30
[24] Patent: EP1847531, 2007, A1, . Location in patent: Page/Page column 43
[25] Patent: CN107226808, 2017, A, . Location in patent: Paragraph 0327; 0340-0342
[26] Patent: US2011/306589, 2011, A1, . Location in patent: Page/Page column 53
[27] Patent: WO2011/154327, 2011, A1, . Location in patent: Page/Page column 136
[28] Patent: EP1903045, 2008, A1, . Location in patent: Page/Page column 43
[29] MedChemComm, 2013, vol. 4, # 2, p. 456 - 462
[30] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1776 - 1787
[31] Patent: WO2003/106459, 2003, A1, . Location in patent: Page 161
[32] Patent: WO2006/70198, 2006, A1, . Location in patent: Page/Page column 126; 139-140
[33] Patent: WO2006/70198, 2006, A1, . Location in patent: Page/Page column 156
[34] Patent: WO2006/70202, 2006, A1, . Location in patent: Page/Page column 80
[35] Patent: WO2006/3440, 2006, A1, . Location in patent: Page/Page column 154
[36] Patent: WO2007/129062, 2007, A1, . Location in patent: Page/Page column 194-195; 199
[37] Patent: WO2016/144848, 2016, A1, . Location in patent: Page/Page column 36
[38] Patent: WO2016/144846, 2016, A1, . Location in patent: Page/Page column 39; 40
[39] Patent: WO2016/144849, 2016, A1, . Location in patent: Page/Page column 31
[40] Patent: WO2016/144844, 2016, A1, . Location in patent: Page/Page column 32
[41] Patent: WO2016/144847, 2016, A1, . Location in patent: Page/Page column 31
[42] Patent: CN107235906, 2017, A, . Location in patent: Paragraph 0090-0093
[43] Patent: WO2018/64135, 2018, A1, . Location in patent: Paragraph 0454-0457
  • 4
  • [ 5334-40-7 ]
  • [ 138786-86-4 ]
Reference: [1] Patent: US2010/21420, 2010, A1,
[2] Patent: US2010/21420, 2010, A1,
[3] Patent: US2010/55094, 2010, A1,
[4] Patent: US2010/55094, 2010, A1,
  • 5
  • [ 67-56-1 ]
  • [ 7719-09-7 ]
  • [ 5334-40-7 ]
  • [ 138786-86-4 ]
YieldReaction ConditionsOperation in experiment
99.5% at 0 - 25℃; for 16 - 48 h; A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with A- nitro-1 H-pyrazole-3-carboxylic acid (1.117 Kg, 7.1 1 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to O to 5 0C, thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 0C overnight, after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 0C, the residue treated with toluene and re-concentrated (3x 2.250 L, 3x 2vol) under reduced pressure at 40 to 45 0C to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5percent).; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in MeOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as a white solid.; Stage 1 : Preparation of 4-nitro-1 H-pvrazole-3-carboxylic acid methyl ester 4-Nitro-1H-pyrazole-3-carboxylic acid (1.350Kg1 8.59 MoI, 1.0 wt) and methanol (10.80L, 8.0 vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to O to 5°C under nitrogen and thionyl chloride (0.702L, 9.62 MoI, 0.52 vol) added at this temperature. The mixture was warmed to 15 to 25°C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6- DMSO). The mixture was concentrated under vacuum at 35 to 45°C and toluene (2.70L, 2.0 vol) charged to the residue and removed under vacuum at 35 to 45°C. The toluene azeotrope was repeated twice using toluene (2.70L, 2.0 vol) to give 4-nitro-1 H-pyrazole-3- carboxylic acid methyl ester [1.467Kg, 99.8percentth, 108.7percent w/w, 1H NMR (d6-DMSO) concordant with structure, no entrained solvent] as an off-white solid.
Reference: [1] Patent: WO2008/9954, 2008, A1, . Location in patent: Page/Page column 83-84; 105
  • 6
  • [ 75-36-5 ]
  • [ 5334-40-7 ]
  • [ 138786-86-4 ]
Reference: [1] Journal of Antibiotics, 2015, vol. 68, # 6, p. 361 - 367
  • 7
  • [ 64-17-5 ]
  • [ 5334-40-7 ]
  • [ 55864-87-4 ]
YieldReaction ConditionsOperation in experiment
98% Reflux A solution of 4-nitro-1H-pyrazole-3-carboxylic acid (2.5 g, 15.9 mmol) in ethanolic HCl (38.3 mL, 1.25M) was refluxed overnight. All volatiles were removed to yield a whitesolid (2.9 g, 98percent) which was used without any further purification. MS: M=186.1 (M+H)+
98% Reflux; Inert atmosphere A solution of 4-nitro-lH-pyrazole-3-carboxylic acid (2.5 g, 15.9 mmol) in ethanolic HQ (38.3 mL, 1.25M) was refluxed overnight. All volatiles were removed to yield a white solid (2.9 g, 98 percent) which was used without any further purification.MS: M = 186.1 (M+H)+
96% at 20℃; for 48 h; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and EPO <DP n="124"/>dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSOd6) δ 14.4 (s, IH), 9.0 (S5 IH)3 4.4 (q, 2H), 1.3 (t, 3H)).
96% at 20℃; for 48 h; 1A. 4-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester; OEtN-NHThionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambienttemperature and the mixture stirred for 48 h. The mixture was reduced in vacuaand dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (*H NMR (400 MHz,DMSO-d6) 8 14.4 (s, 1H), 9.0 (s, 1H), 4.4 (q, 2H), 1.3 (t, 3H)).
96% at 20℃; for 48 h; Preparation VIII; Synthesis of 4-ammo-1H-pyrazole-3-carboxylic acid ethyl esterStep 1. 4-Nitro-1H-pyrazole-3-carboxylic acid ethyl esterThionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3- carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, IH), 9.0 (s, IH), 4.4 (q, 2H), 1.3 (t, 3H)).
96% at 20℃; for 48 h; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) D 14.4 (s, 1 H), 9.0 (s, 1 H), 4.4 (q, 2H), 1.3 (t, 3H)).
96% at 20℃; for 48 h; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) D 14.4 (s, 1 H), 9.0 (s, 1 H), 4.4 (q, 2H), 1.3 (t, 3H)).
96% at 20℃; for 48 h; Step 1. 4-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3- carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, IH), 9.0 (s, IH), 4.4 (q, 2H), 1.3 (t, 3H)).

Reference: [1] Patent: US2011/306589, 2011, A1, . Location in patent: Page/Page column 45
[2] Patent: WO2011/154327, 2011, A1, . Location in patent: Page/Page column 118
[3] Patent: WO2006/70198, 2006, A1, . Location in patent: Page/Page column 122-123
[4] Patent: WO2006/3440, 2006, A1, . Location in patent: Page/Page column 147
[5] Patent: WO2006/77414, 2006, A1, . Location in patent: Page/Page column 142
[6] Patent: WO2006/77424, 2006, A1, . Location in patent: Page/Page column 186
[7] Patent: WO2006/77425, 2006, A1, . Location in patent: Page/Page column 186
[8] Patent: WO2006/77428, 2006, A1, . Location in patent: Page/Page column 163
[9] Patent: WO2008/7123, 2008, A2, . Location in patent: Page/Page column 111
[10] Journal of Medicinal Chemistry, 2008, vol. 51, # 16, p. 4986 - 4999
[11] Patent: WO2005/37797, 2005, A1, . Location in patent: Page/Page column 271-272
  • 8
  • [ 5334-40-7 ]
  • [ 55864-87-4 ]
YieldReaction ConditionsOperation in experiment
96% With thionyl chloride In ethanol at 20℃; for 48 h; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h.
The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, 1H), 9.0 (s, 1H), 4.4 (q, 2H), 1.3 (t, 3H)).
Reference: [1] Patent: WO2005/12256, 2005, A1, . Location in patent: Page/Page column 184
[2] Patent: WO2007/23105, 2007, A1, . Location in patent: Page/Page column 63-64
  • 9
  • [ 75-36-5 ]
  • [ 5334-40-7 ]
  • [ 55864-87-4 ]
Reference: [1] Patent: US2005/197340, 2005, A1, . Location in patent: Page/Page column 68
  • 10
  • [ 5334-40-7 ]
  • [ 74-88-4 ]
  • [ 400877-57-8 ]
YieldReaction ConditionsOperation in experiment
19%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3 h;
Stage #2: at 20℃; for 15 h;
4-Nitropyrazole-3-carboxylic acid (27.5 g, 175 mmol) was dissolved in N,N-dimethylformamide (800 mL) and K2CO3 (53.2 g, 385 mmol) was added at room temperature.
The reaction was heated to 80°C and stirred for 3 hours.
After cooling to room temperature, iodomethane (74.6 g, 525 mmol) was added and the reaction was allowed to react at room temperature for 15 hours.
The reaction solution was diluted with water (2.5 L) and extracted with ethyl acetate (1 L x 2).
The organic phases were combined, washed with saturated aqueous sodium chloride solution (800 mL), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (1:1 petroleum ether / ethyl acetate, Rf1 = 0.5, Rf2 = 0.3) to give methyl 2-methyl-4-nitro-2H-pyrazole-3-carboxylate (6.00 g, as a yellow liquid) with a yield of 19percent, and methyl 1-methyl-4-nitro-pyrazole-3-carboxylate (11.0 g, as a white solid) with a yield of 34percent.
1H NMR: (400 MHz, CDCl3) δ 8.15(s, 1H), 4.01(s, 3H), 4.00(s, 3H). MS-ESI calcd. [M + H]+ 186, found 186.
Reference: [1] Patent: EP3299371, 2018, A1, . Location in patent: Paragraph 0465; 0466; 0467
[2] Patent: WO2017/19804, 2017, A2, . Location in patent: Paragraph 0358
  • 11
  • [ 77-78-1 ]
  • [ 5334-40-7 ]
  • [ 400877-57-8 ]
YieldReaction ConditionsOperation in experiment
30 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14 h; Cooling with ice A)
Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate
To a suspension of 4-nitro-1H-pyrazole-3-carboxylic acid (62 g) and potassium carbonate (221 g) in DMF (700 mL), dimethyl sulfate (121 g) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 14 hours.
The reaction mixture was poured to water, followed by extraction with ethyl acetate.
The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (30 g).
1H NMR (400 MHz, CDCl3) δ 4.01 (3H, s), 4.03 (3H, s), 8.18 (1H, s).
Reference: [1] Patent: EP3287441, 2018, A1, . Location in patent: Paragraph 0293
  • 12
  • [ 67-56-1 ]
  • [ 5334-40-7 ]
  • [ 74-88-4 ]
  • [ 400877-57-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1910 - 1918
  • 13
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  • [ 5334-40-7 ]
  • [ 309740-49-6 ]
YieldReaction ConditionsOperation in experiment
8.62 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; Cooling with ice A)
Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate
To a suspension of 4-nitro-1H-pyrazole-3-carboxylic acid (37 g) and potassium carbonate (97.6 g) in DMF (600 mL), dimethyl sulfate (71.2 g) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 16 hours.
The reaction mixture was poured to water, followed by extraction with ethyl acetate.
The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (8.62 g).
1H NMR (400 MHz, CDCl3) δ 4.02 (3H, s), 4.03 (3H, s), 8.01 (1H, s).
Reference: [1] Patent: EP3287441, 2018, A1, . Location in patent: Paragraph 0305
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