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[ CAS No. 1072-84-0 ] {[proInfo.proName]}

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Chemical Structure| 1072-84-0
Chemical Structure| 1072-84-0
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Product Details of [ 1072-84-0 ]

CAS No. :1072-84-0 MDL No. :MFCD00082203
Formula : C4H4N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NKWCGTOZTHZDHB-UHFFFAOYSA-N
M.W : 112.09 Pubchem ID :14080
Synonyms :
4-Imidazolecarboxylic acid

Calculated chemistry of [ 1072-84-0 ]

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) : -7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.13
Log Po/w (XLOGP3) : -0.08
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -1.21
Log Po/w (SILICOS-IT) : 0.44
Consensus Log Po/w : -0.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.88
Solubility : 14.7 mg/ml ; 0.132 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 15.7 mg/ml ; 0.14 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 : 1.22

Safety of [ 1072-84-0 ]

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 [ 1072-84-0 ]

* 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 [ 1072-84-0 ]
  • Downstream synthetic route of [ 1072-84-0 ]

[ 1072-84-0 ] Synthesis Path-Upstream   1~20

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YieldReaction ConditionsOperation in experiment
89% Reflux Step 1
Synthesis of 1H-imidazole-4-carboxylic acid methyl ester
A stirred solution of 1H-imidazole-4-carboxylic acid (1.0 g, 8.9 mmol), concentrated sulfuric acid (1 mL) in MeOH (30 mL) was heated to reflux overnight.
The mixture was then concentrated under reduced pressure and partitioned between cold water and ethyl acetate.
The organic layer was collected and concentrated under reduced pressure to afford 1 g (89percent) of 1H-imidazole-4-carboxylic acid methyl ester.
87% for 18 h; Reflux 1H-imidazole-4-carboxylic acid (100 g, 892.1 mmol) was added to 800 mL of methanol.Then 100 ml of concentrated sulfuric acid was added. After the addition, the reflux reaction was about 18 h.A small amount of the remaining material was detected by HPLC to terminate the reaction. After treatment: cooling,Concentration under reduced pressure removed most of the methanol. Pour the reaction system into about 1 L of ice water, and adjust the pH to 8-9 with sodium bicarbonate.The organic phase was combined and dried over anhydrous sodium sulfate and filtered.Concentration under reduced pressure gave 97.9 g of pale yellow solid.The yield was 87.0percent.
77% for 24 h; Reflux For synthesis of methyl imidazole-4-carboxylate (5), conc. H2SO4(1.5 mL) was added to a suspension of Im-CO2H (1.00 g, 8.92 mmol)in MeOH (20 mL), and themixture was refluxed for 24 h to give a solutionthat was then cooled to 0 °C and neutralized to pH 8 using 5 MNaOH. Evaporation in vacuo left a white residue that was re-dissolvedin a minimal volume of boiling water; cooling the solution depositedwhite crystals of the ester that were collected, washed with cold H2O(1 × 5 mL), and dried in vacuo at r.t. for 24 h. Yield: 0.87 g (77percent). 1HNMR (DMSO-d6): δ 7.74 (s, 1H, H5-Im), 7.65 (s, 1H, H2-Im), 2.51 (s,3H, CH3-Im). IR: 3105 (N-H, s), 2976, 2846 (C-H, m), 1619 (C=O,m), 1363 (s), 1156 (m), 864 (m). ESI-MS: 127 (M+). Anal. Calcd. forC5H6N2O2: C, 47.62; H, 4.80; N, 22.21. Found: C, 47.5; H, 4.85; N, 21.7.
Reference: [1] Patent: US2010/160323, 2010, A1, . Location in patent: Page/Page column 23-24
[2] Patent: CN108314654, 2018, A, . Location in patent: Paragraph 0086-0088
[3] Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36
[4] Patent: WO2012/143599, 2012, A1, . Location in patent: Page/Page column 79
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YieldReaction ConditionsOperation in experiment
40% at 0℃; 1H-Imidazole-4(5)-carboxylic acid (0.560 g, 5 mmol) was dissolved in DMF (20 mL) and a small amount of insoluble solid was filtered off. A cooled (0 °C) solution of diazomethane in ether36 was added until no more bubbles were formed. After evaporation of the solvent under reduced pressure the residue was dissolved in ether and washed with water to neutral pH. Then the ethereal solution was dried and evaporated. The product was obtained as a white solid homogeneous by TLC in 40percent yield (0.252 g); mp 144-147 °C (mp.lit37 = 153-154 °C).1H NMR (CD3OD) δ: 7.77(d, J = 4.5 Hz, 2H, NCHNHCH), 3.85(s, 3H, CH3).13C NMR δ: 164.2(COO), 138.6, 126.6, 123.4, 52.0(CH3).Anal. Calcd for C5H6N2O2: C, 47.62; H, 4.80; N, 22.21. Found: C, 47.58; H, 4.96; N, 22.12.
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2888 - 2902
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Reference: [1] Patent: US5034539, 1991, A,
[2] Patent: US2014/94474, 2014, A1, . Location in patent: Page/Page column
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Reference: [1] Journal of the Chemical Society, 1916, vol. 109, p. 197
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  • [ 40507-59-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6472 - 6475
[2] Patent: US2012/283280, 2012, A1, . Location in patent: Page/Page column 6-7
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YieldReaction ConditionsOperation in experiment
56%
Stage #1: at 100℃; for 48 h;
Stage #2: at 60℃; for 24 h;
At 100° C., 45.0 g (0.56 mol) of ammonium nitrate are added a little at a time to a solution of 20.0 g (0.18 mol) of 1H-imidazole-4-carboxylic acid in 160 ml of concentrated sulphuric acid.
The reaction mixture is stirred at this temperature for two days and, after cooling, 60 ml of methanol are added carefully and with constant stiffing.
The solution is then stirred at 60° C. for 24 h and, after cooling, poured onto ice.
This results in the precipitation of a fine white solid.
45%
Stage #1: at 100℃; for 48 h;
Stage #2: at 60℃; for 24 h;
Stage #3: With ammonia In water
Ammonium nitrate (3.2 g, 40.2 mmol) was added slowly to a solution of 4imidazolecarboxylic acid (3.0 g, 26.8 mmol) in concentrated sulfuric acid (24 ml) at 100 C. The reaction was heated for 2 days then cooled. Methanol (15 ml) was added cautiously with vigorous stirring and then the reaction heated at 60 C for 24 h. The reaction was cooled and poured onto ice, causing a fine white precipitate to form. The mixture was neutralized by the addition of 33 percent aqueous ammonia. The solid was filtered off and dried to give the title compound (1.24 g, 27percent). A second crop of crystals was collected from the filtrate (0. 82 g, 18percent).'H NMR (400 MHz, DMSO) 8 14.2(1H, brs), 7.94(1H, s), 3.87 (3H, s).
Reference: [1] Patent: US2015/344499, 2015, A1, . Location in patent: Paragraph 1044; 1045; 1046
[2] Patent: WO2005/49613, 2005, A1, . Location in patent: Page/Page column 44
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Reference: [1] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 5; 14; 15; 22
[2] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 5; 14; 15; 22
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Reference: [1] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 4; 5; 7; 8; 21; 22
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YieldReaction ConditionsOperation in experiment
92.49% at 30℃; The mass ratio of 1 H-imidazole-4-carboxylic acid ethyl ester to potassium hydroxide solution was 1: 2.2, the reaction temperature was 30 After the completion of the reaction, the sulfuric acid solution is added, the pH is adjusted to 1, and the crude product is recrystallized from the recrystallization solvent to obtain 1H-imidazole-4-carboxylic acid.
87.96% With potassium hydroxide In water at 65℃; The 2.2g imidazole-4-carboxylic acid ethyl ester in 30 ml water, raising the temperature to 65 °C, stirring next adds by drops 3.3g the mass concentration is 20percent of the reacted with an aqueous solution of KOH to the end point.Adding dilute hydrochloric acid wash filters after adjusting pH to obtain 1H-imidazole-4-carboxylic acid.
Reference: [1] Patent: CN105693619, 2016, A, . Location in patent: Paragraph 0010; 0088; 0089
[2] Patent: CN105622518, 2016, A, . Location in patent: Paragraph 0083; 0094; 0095; 0096; 0097
[3] Patent: CN105622515, 2016, A, . Location in patent: Paragraph 0074; 0075
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Reference: [1] Patent: CN106349166, 2017, A, . Location in patent: Paragraph 0018-0029
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1084 - 1089
[3] Dalton Transactions, 2007, # 34, p. 3771 - 3781
[4] Patent: CN105622515, 2016, A, . Location in patent: Paragraph 0067; 0068; 0069; 0070; 0071
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Reference: [1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 2-3, p. 339 - 345
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Reference: [1] Patent: CN107954938, 2018, A, . Location in patent: Paragraph 0022; 0029; 0036; 0043; 0050
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Reference: [1] Synthetic Communications, 2012, vol. 42, # 5, p. 658 - 666
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Reference: [1] Patent: US4672128, 1987, A,
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Reference: [1] Pharmaceutical Chemistry Journal, 1986, vol. 20, # 7, p. 460 - 463[2] Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 7, p. 799 - 802
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Reference: [1] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 5; 14; 15; 22
[2] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 5; 14; 15; 22
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Reference: [1] Patent: EP1196129, 2005, B1, . Location in patent: Page/Page column 4; 5; 7; 8; 21; 22
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YieldReaction ConditionsOperation in experiment
95% for 18 h; Reflux The imidazole-2-carboxylic acid (5 g, 44.6 mmol) in suspensionin thionyl chloride (75 mL) was heated to reflux under agitation for18 h. The reaction mixture was cooled, then filtered, washed withtoluene, and dried under high vacuum. The compound is obtainedas a yellow solid (95percent yield). C8H4N4O2. MW: 188.14 g/mol. Mp265-268 °C. 1H NMR δ (ppm, 300 MHz, DMSO-d6) 8.24 (d, 1H,CHC-CO), 8.32 (d, 1H, CHC-CO, J3 Hz), 8.88 (d, 1H, CHN),9.28 (d, 1H, CHN, J3 Hz). 13C NMR δ (ppm, 100 MHz, DMSO-d6)123.99, 124.52, 125.62, 137.26, 139.73, 150.39, 159.68. MS (ESI+ ,QTof, m/z): 189.0 [M+H]+.
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 13, p. 6601 - 6610
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 909 - 919
[3] Pharmaceutical Chemistry Journal, 1986, vol. 20, # 7, p. 460 - 463[4] Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 7, p. 799 - 802
[5] Patent: EP1439169, 2004, A1, . Location in patent: Page 81-82
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Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 457 - 460
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