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CAS No. : | 223387-75-5 | MDL No. : | MFCD23136998 |
Formula : | C12H9ClN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OUQVKRKGTAUJQA-UHFFFAOYSA-N |
M.W : | 280.66 | Pubchem ID : | 6914666 |
Synonyms : |
IOX3;YM311
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 68.35 |
TPSA : | 99.52 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.27 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.46 |
Log Po/w (WLOGP) : | 1.41 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 1.43 |
Consensus Log Po/w : | 1.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.26 |
Solubility : | 0.156 mg/ml ; 0.000555 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.19 |
Solubility : | 0.018 mg/ml ; 0.000064 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.52 |
Solubility : | 0.0852 mg/ml ; 0.000303 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.0 |
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: |
* 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 |
---|---|---|
46% | Stage #1: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 24 h; Stage #2: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 12 h; |
General procedure: l-Chloro-4-hydroxyisoquinoline-3-carboxylic acid (300 mg, 1.35 mmol), amino acid methyl ester (1.2 eq), PyBOP (1.2 eq) and Et3N (1.5 mmol) were dissolved in the anhydrous DMF (5 mL) and subsequently stirred at room temperature for 24h. Upon completion of the reaction the DMF was evaporated in vacuo and the resultant residue was suspended in CH2CI2 (20 mL) and washed with H20 (2 x 10 mL). The organic phase was dried over MgS04, filtered and subjected to column chromatography (Biotage SNAP KP- SIL™ 25 g cartridge, eluent system: cHex/EtOAc, ratio for elution of each methyl ester is given along with characterization of final product). The obtained product was dissolved in a mixture of THF/H20 (1 : 1, 10 mL) and subsequently treated with LiOH H20 (5 eq). The reaction was stirred at room temperature for 12h. The THF was evaporated in vacuo and the remaining aqueous solution was neutralized with cone. HC1. If precipitate was formed it was filtered-off and dried in vacuo to yield the desired product. In case that no precipitate was formed, the aqueous solution was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over MgS04, filtered and evaporated in vacuo to yield desired product. 2-(l-Chloro-4-hydroxyisoquinoline-3-carboxamido)acetic acid (20) The desired compound (20) was obtained as a white solid (175 mg, 46percent) starting from 1- Chloro-4-hydroxyisoquinoline-3-carboxylic acid (300 mg, 1.35 mmol). 1H MR (400 MHz, DMSO-i) δ = 9.16 (t, J=6.0 Hz, 1 H, NH), 8.30 (m, 1 H, ArH) 8.24 (m, 1 H, ArH), 7.84 - 8.09 (m, 2 H, ArH) 4.02 (d, J=6.0 Hz, 2 H, CH2) ppm, 13C NMR (101 MHz, DMSO- d6) δ = 171.4, 169.6, 155.1, 139.4, 132.6, 132.5, 130.3, 129.3, 126.9, 123.8, 121.3, 41.7 ppm. Mp = 212-214 °C, HRMS (ESI-TOF) calcd for Ci2H9ClN2Na04 [M+Na+] : 303.0144, found: 303.0143, FT-IR vmax (neat): 3402, 2915, 1712, 1641, 1354, 1255, 794 cm"1. |