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CAS No. : | 23872-36-8 | MDL No. : | MFCD07776617 |
Formula : | C9H6ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRKHLIJRUYVIOY-UHFFFAOYSA-N |
M.W : | 195.60 | Pubchem ID : | 13978439 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.27 |
TPSA : | 53.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 1.1 |
Log Po/w (XLOGP3) : | 2.2 |
Log Po/w (WLOGP) : | 2.52 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 2.5 |
Consensus Log Po/w : | 2.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.89 |
Solubility : | 0.255 mg/ml ; 0.0013 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.22 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.28 |
Solubility : | 0.103 mg/ml ; 0.000528 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
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 |
---|---|---|
426 mg | With barium(II) hydroxide octahydrate; In N,N-dimethyl-formamide; at 50℃; | Step 1 Preparation of 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid 2-chloro-N,N-dimethylacetamide (0.19 ml; 1.84 mmol; 1.20 eq.) was added to a solution of 4-Chloro-1H-indole-3-carboxylic acid (300.00 mg; 1.53 mmol; 1.00 eq.) and barium hydroxide octahydrate (967.67 mg; 3.07 mmol; 2.00 eq.) in DMF (15.63 ml; 202.65 mmol; 132.13 eq.) at 50° C. The reaction mixture was stirred overnight. The reaction mixture was diluted with DMSO (1 ml) and water (1 ml) then submitted to MPLC purification (Yamazen, Interchim 100 g polymeric Reverse Phase column, basic buffer) to afford the desired product 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid (426.00 mg; 1.52 mmol) as a white solid. 1H NMR (400 muMHz, MeOD) delta 7.42 (s, 1H), 6.89-6.79 (m, 1H), 6.78-6.64 (m, 2H), 4.73 (s, 2H), 2.73 (s, 3H), 2.57-2.49 (m, 4H) ppm; [M+H]+ 281.1. LC-MS (254 nm) tR=3.47 min; HPLC (254 nm) Purity: >99percent; tR=2.68 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | 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 20℃; for 4.0h; | Step 1 Preparation of 4-chloro-N-((3,3-difluoro-5-methylcyclohexyl)methyl)-1H-indole-3-carboxamide A mixture of <strong>[23872-36-8]4-chloro-1H-indole-3-carboxylic acid</strong> (0.300 g, 1.5 mmol), (3,3-difluoro-5 methylcyclohexyl)methanamine (0.245 g, 1.5 mmol), HATU (0.684 g, 1.8 mmol) and DIPEA (0.387 g, 3.0 mmol) in DMF (15 mL) was stirred at room temperature for 4 h. The mixture was poured into water (15 mL), extracted with EtOAc (40 mL*3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by column chromatography on silica gel (petroleum ether:EtOAc=5:1) to give 4-chloro-N-((3,3-difluoro-5-methyl-cyclohexyl)methyl)-1H-indole-3-carboxamide (0.110 g, 22percent) as a white solid. |
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