Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 7418-65-7 | MDL No. : | MFCD00234183 |
Formula : | C6H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IASBMUIXBJNMDW-UHFFFAOYSA-N |
M.W : | 138.12 | Pubchem ID : | 319979 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 35.6 |
TPSA : | 76.21 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) : | -6.97 cm/s |
Log Po/w (iLOGP) : | 0.17 |
Log Po/w (XLOGP3) : | 0.25 |
Log Po/w (WLOGP) : | 0.37 |
Log Po/w (MLOGP) : | -1.72 |
Log Po/w (SILICOS-IT) : | 0.03 |
Consensus Log Po/w : | -0.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.23 |
Solubility : | 8.1 mg/ml ; 0.0586 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.41 |
Solubility : | 5.36 mg/ml ; 0.0388 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.01 |
Solubility : | 13.5 mg/ml ; 0.0977 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.09 |
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 |
---|---|---|
27% | Stage #1: With thionyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 3 h; Inert atmosphere Stage #2: With ammonia In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 4 h; |
To a stirred solution of 4-aminopyridine-3-carboxylic acid (3 g, 0.013 mol) in THF (50 mL),SOCh (3.6 mL, 0.045 mol) and catalytic DMF (30 f-lL) were added at RT and stirred for 3 hunder argon atmosphere (TLC indicated complete consumption of the starting material). Thevolatiles were removed under reduced pressure to give the crude product which wasdissolved in THF (30 mL), cooled to 0 °C and 7 N NH3-methanol (22 mL) was added. Thereaction mixture was slowly warmed toRT and stirred for 4 h, the precipitate was filtered, thefiltrate was concentrated under reduced pressure to give the crude compound which waspurified by column chromatography (100-200 silica gel, 60 g, 10percent MeOH-10percent NH40HDCM)to provide 4-aminopyridine-3-carboxamide (475 mg, 27percent) which was used for thenext step without any purification.LCMS (ESI+ ): m/z: 138.33 [M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With lithium hydroxide monohydrate; water In ethanol at 20 - 80℃; for 2 h; | To a stirred solution of methyl 4-aminopyridine-3-carboxylate (2 g, 13.15 mmol) in EtOHwater(120 mL, 1:1), LiOH·H20 (1.21 g, 28.80 mmol) was added at RT and heated at 80 °Cfor 2 h (TLC indicated complete consumption of starting material). The volatiles wereremoved under reduced pressure to give the crude compound which was dissolved in water(30 mL), washed with EtOAc (2 x 25 mL) to remove the non-polar impurities. The aqueouslayer was acidified with 1 N HCl till pH= 1, and extracted with EtOAc (2 x 10 mL). Thecombined organic extracts were concentrated under reduced pressure to give the cruderesidue which was crystallized from MeOH (20 mL) to obtain 4-aminopyridine-3-carboxylicacid (1 g, 55percent) as an off-white solid.LCMS (ESI+): m/z: 139.31 [M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17 g | With ammonia In water at 150℃; | A solution of 4-chloropyridine-3-carboxylic acid (15 g, 0.095 mol) in aqueous NH3 (600 mL) was heated in a pressure vessel at 150 °C overnight. The progress of reaction was monitored by TLC. After completion of reaction, the mixture was concentrated under reduced pressure. To this reaction mixture was added toluene (2x100 mL) to obtain 4-aminopyridine-3-carboxylic acid (17 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Reflux; Cooling | Step a): Methyl 4-aminopyridine-3-carboxylate A little at a time, 4400 mg (31.86 mmol) of 4-aminopyridine-3-carboxylic acid are added to 12 ml of ice-cooled concentrated sulfuric acid. 70 ml of methanol are then added slowly. The reaction mixture is stirred under reflux (oil bath temperature 75° C.) for 20 h. The reaction solution is poured onto about 120 g of ice and neutralized with sodium carbonate. After extraction with dichloromethane, the organic phase is dried over magnesium sulfate and filtered. After 24 h of standing, the title compound crystallizes from the filtrate. Yield: 3310 mg (67percent of theory) LC-MS (Method 9): Rt=1.59 min; MS (ESIpos): m/z=153 [M+H]+. |
10.3 g | at 0 - 85℃; | To a solution of 4-aminopyridine-3-carboxylic acid (17 g, 0.123 mol) in MeOH (300 mL) was added H2SO4 (45 mL) dropwise at 0 °C. The reaction mixture was heated to reflux at 85 °C overnight. The progress of reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated under reduced pressure to remove MeOH, residue was basified with a saturated aqueous solution of Na2C03 (400 mL), extracted with EtOAc (3x500 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford methyl 4-aminopyridine-3-carboxylate (10.3 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With dmap In tetrahydrofuran; water at 20℃; for 3 h; | Intermediate 6AH: 4- fcr<-Butoxycarbonylamino)pyridine-3-carboxylic acidTo a stirred solution of 4-aminopyridine-3-carboxylic acid (1.0 g, 7.2 mmol), Boc anhydride in THF: water (1: 1, 20mL) was added DMAP and stirred for 3 h at room temperature. To this was added ethyl acetate (25 mL) and water (25 mL). Aqueous layer was separated, extracted with ethyl acetate (25 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to furnish 1.2 g (69percent) of 4-(ieri-butoxycarbonylamino)pyridine-3-carboxylic acid.MS (ES) m/z 239.1 (M+l). |
69% | With dmap In tetrahydrofuran; water at 20℃; for 3 h; | To a stirred solution of 4-aminopyridine-3-carboxylic acid (1.0 g, 7.2 mmol), Boc anhydride in THF:water (1:1, 20 mL) was added DMAP and stirred for 3 h at room temperature. To this was added ethyl acetate (25 mL) and water (25 mL). Aqueous layer was separated, extracted with ethyl acetate (25 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to furnish 1.2 g (69percent) of 4-(tert-butoxycarbonylamino)pyridine-3-carboxylic acid. [0349] MS (ES) m/z 239.1 (M+1) |
[ 24242-19-1 ]
5-Amino-3-pyridinecarboxylic acid
Similarity: 0.83
[ 3167-49-5 ]
6-Amino-3-pyridinecarboxylic acid
Similarity: 0.75
[ 14208-83-4 ]
Ethyl 3-amino-4-pyridinecarboxylate
Similarity: 0.74
[ 24242-19-1 ]
5-Amino-3-pyridinecarboxylic acid
Similarity: 0.83
[ 3167-49-5 ]
6-Amino-3-pyridinecarboxylic acid
Similarity: 0.75
[ 24242-19-1 ]
5-Amino-3-pyridinecarboxylic acid
Similarity: 0.83
[ 4591-55-3 ]
Dimethyl pyridine-3,5-dicarboxylate
Similarity: 0.79