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CAS No. : | 212197-74-5 | MDL No. : | MFCD11897503 |
Formula : | C6H3NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HHHCADSYQQJUGV-UHFFFAOYSA-N |
M.W : | 137.09 | Pubchem ID : | 10855516 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.38 |
TPSA : | 74.23 Ų |
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) : | -6.5 cm/s |
Log Po/w (iLOGP) : | 0.86 |
Log Po/w (XLOGP3) : | 0.9 |
Log Po/w (WLOGP) : | 0.85 |
Log Po/w (MLOGP) : | -0.92 |
Log Po/w (SILICOS-IT) : | 0.62 |
Consensus Log Po/w : | 0.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.56 |
Solubility : | 3.77 mg/ml ; 0.0275 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.04 |
Solubility : | 1.24 mg/ml ; 0.00904 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.04 |
Solubility : | 12.5 mg/ml ; 0.091 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.51 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With hydroxylamine hydrochloride In pyridine at 85℃; Stage #2: With acetic anhydride In pyridine at 85℃; for 3 h; |
To a solution OF 2-FORMYL-5-FURANCARBOXYLIC acid (0.28 g, 2.0 mol) in pyridine (5.0 mL) was added hydroxylamine hydrochloride ("NH20H-HC1") (0.27 g, 4.0 mol). The mixture was heated to 85 °C before the addition of acetic anhydride (4.0 ml). The reaction mixture was stirred at 85 °C for 3 h, cooled to 60 °C and poured into water (25 mL). The mixture was cooled to room temperature and stirred overnight (the pH of the solution was measured to be 5-6). The impurities were extracted with a solution of 4/1 DCM/ISOPROPANOL (3 x 30 mL). The aqueous layer was then basified with NAOH solution (2 N) to A pH of about 9, and the pyridine was extracted with a solution of 4/1 DCM/isopropanol (3 x 30 mL). The aqueous solution was then acidified to a pH of about 2 and the product was extracted with a solution of 3/1 DCM/isopropanol (3 x 50 mL). The combined organic extracts were dried over MGS04, and the solvent was evaporated to afforded the pure product as a light brown solid in 90 percent yield NMR (DMSO-d6) : 6 13. 80 (bs, 1H), 7.75 (d, 1H), 7.40 (d, 1H). IR (neat): (cm-1) 3200,2250, 1053,1025, 1006. |
90% | Stage #1: at 85℃; for 3 h; Stage #2: With sodium hydroxide In water Stage #3: Acidic aqueous solution |
EXAMPLE 6 (Preparation of 5-Cyano-furan-2-carboxylic acid [5-hydroxymethyl-2-(4- methyl-piperidin- 1 -yl)-phenyl] -amide); A. 2-Cvano-5-furancarboxylic acid; To a solution of 2-formyl-5-furancarboxylic acid (0.28 g, 2.0 mol) in pyridine (5.0 niL) was added hydroxylamine hydrochloride ("NH2OH-HCl") (0.27 g, 4.0 mol). The mixture was heated to 85 0C before the addition of acetic anhydride (4.0 ml). The reaction mixture was stirred at 85 0C for 3 h, cooled to 60 0C and poured into water (25 mL). The mixture was cooled to room temperature and stirred overnight (the pH of the solution was measured to be 5-6). The impurities were extracted with a solution of 4/1 DCM/isopropanol (3 x 30 mL). The aqueous layer was then basified with NaOH solution (2 N) to a pH of about 9, and the pyridine was extracted with a solution of 4/1 DCM/isopropanol (3 x 30 mL). The aqueous solution was then acidified to a pH of about 2 and the product was extracted with a solution of 3/1 DCM/isopropanol (3 x 50 mL). The combined organic extracts were dried over MgSO4, and the solvent was evaporated to afforded the pure product as a light brown solid in 90 percent yield. 1H NMR (DMSO-d6): δ 13.80 (bs, IH), 7.75 (d, IH), 7.40 (d, IH). IR (neat): (cm"1) 3200, 2250, 1053, 1025, 1006. |
76% | Stage #1: at 85℃; for 3 h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In water |
5-Cyano-furan-2-carboxylic acid A 250-mL, three-neck, round-bottom flask equipped with a mechanical stirrer, a heating mantle, and a condenser was charged with 5-formyl-2-furancarboxylic acid (9.18 g, 65.6 mmol) and pyridine (60 mL). Hydroxylamine hydrochloride (5.01 g, 72.2 mmol) was added and the mixture was heated to 85° C. Acetic anhydride (40 mL) was added and the reaction was stirred at 85° C. for 3 h, after which time the solvent was evaporated at 40° C. under reduced pressure. The residue was dissolved in water, basified with 2.0 N NaOH solution to pH 9, and extracted with 4:1 dichloromethane/2-propanol until the pyridine was completely removed (5*200 mL). The aqueous solution was then acidified with 2.0 N HCl solution to pH 2, saturated with solid NaCl, and extracted with 4:1 dichloromethane/2-propanol (5*200 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to dryness. The residue was crystallized from dichloromethane to give 6.80 g of the title compound as a white solid (76percent). Mass spectrum (ESI-neg, m/z) Calcd. for C6H3NO3, 136.0 (M-H). found 136.1. The 1H NMR spectrum was consistent with the assigned structure. |
76% | Stage #1: With hydroxylamine hydrochloride In pyridine at 85℃; for 3 h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In water |
A 250-mL, three-neck, round-bottom flask equipped with a mechanical stirrer, a heating mantle, and a condenser was charged with 5- formyl-2-furancarboxylic acid (9.18 g, 65.6 mmol) and pyridine (60 mL). Hydroxy lamine hydrochloride (5.01 g, 72.2 mmol) was added and the mixture was heated to 85° C. Acetic anhydride (40 mL) was added and the reaction was stirred at 85° C for 3 h, after which time the solvent was evaporated at 40° C under reduced pressure. The residue was dissolved in water, basified with 2.0 N NaOH solution to pH 9, and extracted with 4: 1 dichloromcthanc^-propanol until the pyridine was completely removed (5 x 200 mL). <n="85"/>The aqueous solution was then acidified with 2.0 N HCl solution to pH 2, saturated with solid NaC 1 , and extracted with 4:1 dichlbromethane /2-propanol (5 x 200 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to dryness. The residue was crystallized from dichloromethane to give 6.80 g of the title compound as a white solid (76percent). Mass spectrum (ESI-neg, m/z) Calcd. forC6H3NO3, 136.0 (M-H), found 136.1. The 1H NMR spectrum was consistent with the assigned structure. |
46% | Stage #1: at 85℃; Stage #2: at 85℃; for 3 h; |
Example 15-Cyano-furan-2-carboxylic acid; To 2.8 g of 2-formyl-5-furancarboxylic acid (20 mmol) and 2.7 g of hydroxylamine hydrochloride (40 mmol) under Ar was added and dry pyridine (50 mL). The mixture was heated to 85 °C, acetic anhydride (40 mL) was added and the mixture was stirred for 3 h. After cooling to 60 °C, water (250 mL) was added and the mixture was stirred at RT for 70 h. The mixture was acidified to pH 2 with concentrated hydrochloric acid and extracted with 3:1 dichloromethane-isopropanol (8 x 100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anh sodium sulfate and concentrated in vacuo to afford the title compound as a tan solid (1.26 g, 46 percent). 1H-NMR (CD3OD; 400 MHz): δ 14.05 (br s, IH), 7.74 (d, IH, J = 3.8 Hz), 7.42 (d, IH, J = 3.8 Hz).; A 250-mL, three-neck, round-bottom flask equipped with a mechanical stirrer, a heating mantle, and a condenser was charged with 5-formyl-2-furancarboxylic acid (9.18 g, 65.6 mmol) and pyridine (60 mL). Hydroxylamine hydrochloride (5.01 g, 72.2 mmol) was added and the mixture was heated to 85° C. Acetic anhydride (40 ihL) was added and the reaction was stirred at 85° C for 3 h, after which time the solvent was evaporated at 40° EPO <DP n="147"/>C under reduced pressure. The residue was dissolved in water, basified with 2.0 N NaOH solution to pH 9, and extracted with 4:1 dichloromethane/2-propanol until the pyridine was completely removed (5 x 200 mL). The aqueous solution was then acidified with 2.0 N HCl solution to pH 2, saturated with solid NaCl, and extracted with 4:1 dichloromethane /2-propanol (5 x 200 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to dryness. The residue was crystallized from dichloromethane to give 6.80 g of the title compound as a white solid (76percent). Mass spectrum (ESI-neg, m/z) Calcd. for C6H3NO3, 136.0 (M-H), found 136.1. The 1H NMR spectrum was consistent with the assigned structure. |
46% | Stage #1: at 85℃; for 3 h; Stage #2: With hydrogenchloride In water at 20 - 60℃; for 70 h; |
To a flask with a stir bar and Vigreaux column under Ar was added 2-formyl-5-furancarboxylic acid (2.8 g, 20 mmol), hydroxylamine hydrochloride (2.7 g, 40 mmol), and dry pyridine (50 mL). The mixture was heated to 85° C., acetic anhydride (40 mL) was added and the mixture was stirred for 3 h. After cooling to 60° C., water (250 mL) was added and the mixture was stirred at RT for 70 h. The mixture was acidified to pH 2 with concentrated hydrochloric acid and extracted with 3:1 dichloromethane-isopropanol (8.x.100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anh sodium sulfate and concentrated in vacuo to afford the title compound as a tan solid (1.26 g, 46 percent). 1H-NMR (CD3OD; 400 MHz): δ 14.05 (br s, 1H), 7.74 (d, 1H, J=3.8 Hz), 7.42 (d, 1H, J=3.8 Hz).; A 250-mL, three-neck, round-bottom flask equipped with a mechanical stirrer, a heating mantle, and a condenser was charged with 5-formyl-2-furancarboxylic acid (9.18 g, 65.6 mmol) and pyridine (60 mL). Hydroxylamine hydrochloride (5.01 g, 72.2 mmol) was added and the mixture was heated to 85° C. Acetic anhydride (40 mL) was added and the reaction was stirred at 85° C. for 3 h, after which time the solvent was evaporated at 40° C. under reduced pressure. The residue was dissolved in water, basified with 2.0 N NaOH solution to pH 9, and extracted with 4:1 dichloromethane/2-propanol until the pyridine was completely removed (5.x.200 mL). The aqueous solution was then acidified with 2.0 N HCl solution to pH 2, saturated with solid NaCl, and extracted with 4:1 dichloromethane/2-propanol (5.x.200 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to dryness. The residue was crystallized from dichloromethane to give 6.80 g of the title compound as a white solid (76percent). Mass spectrum (ESI-neg, m/z) Calcd. for C6H3NO3, 136.0 (M-H), found 136.1. The 1H NMR spectrum was consistent with the assigned structure. |
46% | With pyridine; hydroxylamine hydrochloride; acetic anhydride In water | a) 5-Cyano-furan-2-carboxylic Acid To 2.8 g of 2-formyl-5-furancarboxylic acid (20 mmol) and 2.7 g of hydroxylamine hydrochloride (40 mmol) under Ar was added and dry pyridine (50 mL). The mixture was heated to 85° C., acetic anhydride (40 mL) was added and the mixture was stirred for 3 h. After cooling to 60° C., water (250 mL) was added and the mixture was stirred at RT for 70 h. The mixture was acidified to pH 2 with concentrated hydrochloric acid and extracted with 3:1 dichloromethane-isopropanol (8*100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anh sodium sulfate and concentrated in vacuo to afford the title compound as a tan solid (1.26 g, 46percent). 1H-NMR (CD3OD; 400 MHz): δ 14.05 (br s, 1H), 7.74 (d, 1H, J=3.8 Hz), 7.42 (d, 1H, J=3.8 Hz). |
46% | Stage #1: at 85℃; for 3 h; Stage #2: at 20 - 60℃; for 70 h; Stage #3: With hydrogenchloride In water |
Example 1 5-Cyano-furan-2-carboxylic acid To a flask with a stir bar and Vigreaux column under Ar was added 2-formyl-5-furancarboxylic acid (2.8 g, 20 mmol), hydroxylamine hydrochloride (2.7 g, 40 mmol), and dry pyridine (50 mL). The mixture was heated to 85° C., acetic anhydride (40 mL) was added and the mixture was stirred for 3 h. After cooling to 60° C., water (250 mL) was added and the mixture was stirred at RT for 70 h. The mixture was acidified to pH 2 with concentrated hydrochloric acid and extracted with 3:1 dichloromethane-isopropanol (8*100 mL). The combined organic layers were washed with water (1000 mL), brine (100 mL), dried over anh sodium sulfate and concentrated in vacuo to afford the title compound as a tan solid (1.26 g, 46percent). 1H-NMR (CD3OD; 400 MHz): δ 14.05 (br s, 1H), 7.74 (d, 1H, J=3.8 Hz), 7.42 (d, 1H, J=3.8 Hz). |
46% | Stage #1: With hydroxylamine hydrochloride; acetic anhydride In pyridine at 85℃; for 3 h; Stage #2: With water In pyridine at 20 - 60℃; for 70 h; Stage #3: With hydrogenchloride In pyridine |
To a flask with a stir bar and Vigreaux column under Ar was added 2-formyl-5- furancarboxylic acid (2.8 g, 20 mmol), hydroxylamine hydrochloride (2.7 g, 40 mmol), and dry pyridine (50 mL). The mixture was heated to 85 0C, acetic anhydride (40 mL) was added and the mixture was stirred for 3 h. After cooling to 60 0C, water (250 mL) was added and the mixture was stirred at RT for 70 h. The mixture was acidified to pH 2 with concentrated hydrochloric acid and extracted with 3:1 dichloromethane-isopropanol (8 x 100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anh sodium sulfate and concentrated in vacuo to afford the title compound as a tan solid (1.26 g, 46 percent). 1H- <n="61"/>NMR (CD3OD; 400 MHz): δ 14.05 (br s, IH), 7.74 (d, 1 H, J = 3.8 Hz), 7.42 (d, IH, J = 3.8 Hz). |
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