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[ CAS No. 1621-91-6 ] Pyrazole-3-carboxylic acid

Cat. No.: A116703
Chemical Structure| 1621-91-6
Chemical Structure| 1621-91-6
Structure of 1621-91-6 * Storage: Keep in dark place,Sealed in dry,Room Temperature
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Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Product Details of [ 1621-91-6 ]

CAS No. :1621-91-6 MDL No. :MFCD00077436
Formula : C4H4N2O2 Boiling Point : -
Linear Structure Formula :HO(O)CC3H3N2 InChI Key :KOPFEFZSAMLEHK-UHFFFAOYSA-N
M.W : 112.09 Pubchem ID :574310
Synonyms :
Chemical Name :1H-Pyrazole-3-carboxylic acid

Calculated chemistry of [ 1621-91-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.55
TPSA : 65.98 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) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.04
Log Po/w (XLOGP3) : 0.07
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -0.81
Log Po/w (SILICOS-IT) : 0.44
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.98
Solubility : 11.9 mg/ml ; 0.106 mol/l
Class : Very soluble
Log S (Ali) : -1.01
Solubility : 11.0 mg/ml ; 0.0979 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.55
Solubility : 31.7 mg/ml ; 0.282 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 1621-91-6 ]

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 [ 1621-91-6 ]

* 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 [ 1621-91-6 ]

[ 1621-91-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 64-17-5 ]
  • [ 1621-91-6 ]
  • [ 5932-27-4 ]
YieldReaction ConditionsOperation in experiment
96% With sulfuric acid; at 80℃; for 2h; To solution of ethanol (50 mL) and 3-pyrazolecarboxylicacid (1.112 g 10 mmol) at 80 °C was added concentratedsulfuric acid (2 mL), and after 2 h of stirring theethyl 1H-pyrazole-3-carboxylate was obtained (1.350 g,9.6 mmol, 96 percent).
93% With sulfuric acid; at 100℃; for 4h;Inert atmosphere; Ethyl 1H-pyrazole-3-carboxylate (6) A 100 mL Schlenk tube was dried under vacuum, filled with nitrogen and charged with 0.5 g (4.461 mmol, 1.0 eq) 1H-pyrazol-3-carboxylic acid which was dissolved in 20 mL EtOH. After adding 1.31 g (0.72 mL, 13.382 mmol, 3.0 eq) conc. H2SO4 the colorless reaction mixture was heated to reflux (100° C.) and stirred at this temperature for 4 h. TLC analysis (DCM/MeOH 95:5) indicated full conversion of the starting material. After cooling to rt the mixture was transferred to a flask to remove the solvent at a rotary evaporator. The colorless residue was diluted in 20 mL water and neutralized with 17 mL saturated aqueous NaHCO3 solution. Thereby a white solid precipitated. The aqueous layer was extracted with EtOAc (4*50 mL), dried over MgSO4 and the solvent was evaporated under reduced pressure to yield the pure title compound. yield: 582.5 mg (93percent); colorless solid; M.p.: 158-161° C.; Rf (DCM/MeOH 95:5): 0.42; 1H-NMR (300 MHz, CDCl3): delta (ppm)=10.69 (bs, 1H, NH), 7.84 (d, 4J=2.1 Hz, 1H, Ar-H), 6.86 (d, 4J=2.1 Hz, 1H, Ar-H), 4.43 (q, 3J=7.2 Hz, 2H, CH2), 1.41 (t, 3J=7.2 Hz, 3H, CH3); 13C-NMR (75.5 MHz, CDCl3): delta (ppm)=161.8 (C=O), 141.6 (Cq), 132.3 (CHAr), 107.8 (CHAr), 61.1 (CH2), 14.3 (CH3); GC-MS (NM-50_S2): tR=4.655 min (m/z=140.1, 98.0percent M+, BP: 95.0).
92% With sulfuric acid;Reflux; 1H-pyrazol-3-formic acid (7.25 g, 64.7 mmol) was dissolved in absolute ethanol (100 mL), and concentrated sulfuric acid (0.7 mL) was added. The reaction liquid was heated and refluxed overnight. The reaction liquid was concentrated in vacuo, and the residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate, and extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give ethyl 1H-pyrazol-3-formate (8.35g, 92percent yield), as a off-white solid. 1H NMR (400MHz, CDCl3) delta 12.4 (brs, 1H), 7.74 (d, J = 2.4 Hz, 1H), 6.86 (d, J = 2.4 Hz, 1H), 4.42 (q, J = 7.2 Hz, 2H), 1.41 (t, J = 7.2 Hz, 3H).
80% With sulfuric acid;Heating / reflux; 1 H-Pyrazole-3-carboxylic acid (2.0 g, 17.84 mmol) was dissolved in ethanol (20 ml_), sulfonic acid (1 ml_) was added and the reaction mixture was heated to reflux overnight. Evaporation in vacuo followed by addition of water and aqueous sodium carbonate gave a white precipitate. Filtration followed by wash with water gave 1 H- pyrazole-3-carboxylic acid ethyl ester (2.0 g, 80percent) as white crystals.
72% With sulfuric acid; for 24h;Reflux; General procedure: To a suspension of 4-methoxy-3,5-dimethylbenzoic acid (4 g, 22.2 mmol) in MeOH (60 mL) sulphuric acid was added (1 mL) and mixture stirred at reflux for 1 day. Water was added and it was extracted with AcOEt, organic layers were put together and dried over sodium sulphate and concentrated. The oil thus obtained was purified by normal phase chromatography with 5percent MeOH/DCM to yield the title compound as a colorless oil (99percent yield). LRMS: m/z 195 (M+1)+ Retention time: 6.17 min (Method B) 1H NMR (250 MHz, DMSO-d6) delta ppm 2.30 (s, 6 H) 3.74 (s, 3 H) 3.87 (s, 3 H) 7.71 (s,2H).; Obtained (72percent) from 1H-pyrazole-3-carboxylic acid following the procedure described in Preparation 117, using ethanol as solvent. LRMS: m/z 139 (M-1)+ Retention time: 2.13 min (Method A)
72% With sulfuric acid; for 12h;Reflux; Example 14A1 lH-Pyrazole-3-carboxylic acid ethyl ester To a solution of lH-pyrazole-3-carboxylic acid (2.0 g, 17.8 mmol) in anhydrous ethanol (20 mL) was added concentrated H2SO4 (1 mL) at room temperature. The mixture was refluxed for 12 hours. TLC (neat EtOAc) indicated that the reaction was completed. The mixture was concentrated, the residue was washed with aqueous NaHC03 (20 mL), extracted with dichloromethane (50 mL x 3). The organic layer was dried over Na2S04, filtered, and concentrated in vacuum to give Example 14A1 (1.8 g, yield 72percent) as a white solid.
Description 1; Ethyl 1H-pyrazole-3-carboxylate (D1); 1 H-pyrazole-3-carboxylic acid (1.Og, 8.9 mmol), was dissolved in ethanol (~12ml) and sulphuric acid added (1.5ml). the solution was heated at reflux overnight. The reaction mixture was concentrated in vacuo and water (-2OmI) added, the solution was neutralised with sodium bicarbonate. Ethylacetate (~70ml) was added and the layers partitioned, the aq was extracted with ethylacetate (~70ml) and the combined organics were dried (MgSO4) and concentrated in vacuo to yield the title compound as a white solid (1.21g, 8.64 mmol). deltaH (CDCI3, 400 MHz): 7.77 (1 H, d), 6.86 (1 H, d),4.43 (2H, quart), 1.42 (3H, t).
With sulfuric acid; for 20h;Heating / reflux; 1 - ( [2-(trimethylsilyl)ethoxy]methyl) - lH-pyrazole-3 -carbaldehyde was prepared as follows: 3-Methyl pyrazole (50 g, 0.61 mol) was placed in a 5 L round-bottom flask equipped with mechanical stirrer. 3 L of water was added and heated to 80 C. KMn04 (211.90 g, 1.34 mol) was added portion wise and refluxed for 4.5 h. After stirring at rt overnight, solid was filtered and washed with water. The water was removed in vacuo and 100 mL of water was kept in the flask which was acidified with 1 N HCl to pH 4. It was extracted with EtOAc (2x 1L), washed with brine (2x150 mL), dried over MgS04, filtered and removed in vacuo to yield 1H-pyrazole-3-carboxylic acid (38 g, 56percent) as a white solid. 38 g (0.34 mol) of IH-pyrazole-3-carboxylic acid was refluxed in anhydrous ethanol (1 L) and conc. sulfuric acid (60 mL) for 20 h under nitrogen. Ethanol was removed and crude was basified to pH 8. Precipitated solid was filtered. The filtrate was extracted with THF/CHC13 (2: 3, 3x 1 L), dried over MgS04, filtered and removed in vacuo to yield ethyl 1H-pyrazole-3- carboxylate (39 g, 82percent) as a white solid. To a suspension of ethyl 1H-pyrazole-3-carboxylate (4.42 g, 31.57 mmol) in 1,4-dioxane (140 mL) under N2 atmosphere at 0 C was added NaH (0.91 g, 37.88 mmol) and stirred for 15 min. Neat SEM-Cl (5.79 g, 34.73 mmol) was added drop wise to reaction mixture and stirred overnight at rt. It was quenched with water (30 mL) and excess 1,4-dioxane was removed in vacuo. The residue was extracted with EtOAc (2x250 mL), washed with water (1x50 mL), dried over MgS04, filtered and removed in vacuo to give crude ethyl 1 - [2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.84 g) as a yellow oil. The crude material was used in next step without purification. To a suspension of LiAlH4 in THF (100 mL) at 0 C under N2 atmosphere was added a solution of ethyl 1- f [2-(trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.88 g, 32.88 mmol) slowly. After addition was completed the cooling bath was removed and reaction mixture was stirred overnight. It was quenched with water (10 mL) carefully at 0 C. THF was removed and residue was diluted with DCM (250 mL) and organic layer was separated, dried over MgS04 and removed in vacuo. The crude material was plugged thru a pad of silica gel with EtOAc/hexanes (from 10percent to 100percent) to yield (1-[2- (trimethylsilyl)ethoxy]methyl) -lH-pyrazol-3-yl)methanol (5.80 g, 77percent) as an yellow oil. 53.75 g (0.24 mol) of (1- f [2-(trirnethylsilyl)ethoxy]methyl}-1H pyrazol-3-yl)methanol was dissolved in THF and 122.97 g (1.41 mol) of Mn02 was added. The resulting mixture was refluxed for 60 h. Solid material was filtered through a pad of celite and washed with hot THF. The filtrate was removed in vacuo to give crude product. The crude was plugged thru a pad of silica gel and eluted with EtOAc/hexanes (from 20percent to 50percent) to yield 1-[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carbaldehyde (50.88 g, 86.5percent) as a red oil.

  • 3
  • [ 908094-01-9 ]
  • [ 1621-91-6 ]
  • [ 17827-60-0 ]
  • 1,2-dimethylpyrazolium-5-carboxylate [ No CAS ]
  • 4
  • [ 1621-91-6 ]
  • [ 116008-52-7 ]
YieldReaction ConditionsOperation in experiment
Scheme 33--Route to Preferred Groups 49 [4,3-d] ring fusion Nitration of pyrazole-3-carboxylic acid followed by reduction gives 4-aminopyrazole-3-carboxylic acid.
  • 5
  • [ 5932-27-4 ]
  • [ 221300-34-1 ]
  • [ 881668-91-3 ]
  • [ 1621-91-6 ]
YieldReaction ConditionsOperation in experiment
(b) 4-Fluoropyrazole-3-carboxylic acidSodium hydroxide (aq., 2M, 18 mmol; 9 mL) was added to a solution of a mixture (-2:1) of 4-fluoro<strong>[5932-27-4]pyrazole-3-carboxylic acid ethyl ester</strong> and <strong>[5932-27-4]pyrazole-3-carboxylic acid ethyl ester</strong> (1.2 g, ~8 mmol; see step (a) above) in dioxane (9 mL) at rt and was stirred for 16 h. A second portion of aqueous sodium hydroxide (2M, 18 mmol, 9 mL) was added and the mixture was stirred for another 4 h. The mixture was acidified with HCl (aq., 2M, 20 mL), concentrated, stirred with MeOH (30 mL) and filtered. The filtrate was concentrated and the residue crystallised from HCl (aq., 0.01M)<to give a mixture (-3:1) of the sub-title compound and pyrazole- 3-carboxylic acid as a white solid (Yield: 267 mg (-2 mmol, ~25percent)). This mixture was employed without further purification.1H-NMR (DMSO-d6): delta 13.7-13.1 (br s, 1.3H), 7.9-7.7 (m, IH), 7.73 (d, 0.3H), 6.70 (d, 0.3H).
With sodium hydroxide; water; In 1,4-dioxane; at 20℃; for 20h; 4-Fluoropyrazole-3-carboxylic acid Aqueous NaOH (2M, 18 mmol, 9 mL) was added to a solution of a mixture (~2:1) of 4-fluoro<strong>[5932-27-4]pyrazole-3-carboxylic acid ethyl ester</strong> and <strong>[5932-27-4]pyrazole-3-carboxylic acid ethyl ester</strong> (1.2 g, ~8 mmol; see step (a) above) in dioxane (9 mL) at room temperature and was stirred for 16 h. A second portion of aqueous NaOH (2M5 18 mmol, 9 mL) was added and the mixture was stirred for another 4 h. The mixture was acidified with aqueous HCl (2M, 20 mL), concentrated, stirred with MeOH (30 mL) and filtered. The filtrate was concentrated and the residue was crystallised with aqueous HCl (0.0 IM) to give a mixture (-3:1) of the sub-title compound and pyrazole-3-carboxylic acid as a white solid (Yield: 267 mg (~2 mmol, -25percent)). This mixture was employed without further purification. 1H-NMR (DMSO-d6): delta 13.7-13.1 (br s, 1.3H), 7.9-7.7 (m, IH), 7.73 (d, 0.3H), 6.70 (d, 0.3H)
  • 6
  • [ 5932-27-4 ]
  • [ 1621-91-6 ]
YieldReaction ConditionsOperation in experiment
51% A 2M aqueous sodium hydroxide solution (1.8 mL, 3.6 mmol) was added to a solution of ethyl 1 H-pyrazole-4-carboxylate (0.2g, 1.55 mmol) in ethanol (4 mL). The reaction mixture was stirred at room temperature overnight and at 80 °C for 2 further hours. The ethanol was evaporated and the mixture was neutralized to give a precipitate which was filtered and dried to give the title compound (0.089 g, 51percent) as a white solid.LRMS (m/z): 113 (M+1)+.
51% With water; sodium hydroxide; In ethanol; at 20 - 80℃;   <strong>[5932-27-4]ethyl 1H-pyrazole-4-carboxylate</strong> (0.2g, 1.55 mmol) in   ethanol (4 mL). The reaction mixture was stirred at room temperature overnight and at 80 °C for 2 further hours. The ethanol was evaporated and the mixture was neutralized to give a precipitate which was filtered and dried to give the   title compound (0.089 g, 51 percent) as a white solid.LRMS (m/z): 113 (M+1)+.
  • 8
  • [ 75051-55-7 ]
  • [ 1621-91-6 ]
  • tert-butyl N-[2-(1H-pyrazole-3-carbonylamino)oxyethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 40℃; Tert-butyl N-(2-aminooxyethyl)carbamate (510 mg, 2.90 mmol), HATU (932 mg, 2.45 mmol) and DIPEA (1 .16ml_, 6.69 mmol) were added to a solution of 1 H-pyrazole-3- carboxylic acid (250 mg, 2.23 mmol) in DMF (1 1 ml_). The mixture was stirred at 40C overnight. After concentration, addition of water and extraction with AcOEt, the organic layer was dried over Na2S04, filtered and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (DCM/acetone: 100/0 to 70/30) to provide intermediate (46a) (575 mg, 2.13 mmol, 95%).MS m/z ([M+H]+) 271 .1H NMR (400 MHz, DMSO-d6): δ (ppm) 1 .39 (s, 9H), 3.14-3.22 (m, 2H), 3.80 (t, J = 5.2 Hz, 2H), 6.66 (s, 1 H), 6.82 (t, J = 5.5 Hz, 1 H), 7.84 (s, 1 H), 1 1 .37 (s, 1 H), 13.31 (s, 1 H).
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