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CAS No. : | 89673-36-9 | MDL No. : | MFCD22056377 |
Formula : | C13H15NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CNFLHJOYSZBEEL-UHFFFAOYSA-N |
M.W : | 249.33 | Pubchem ID : | 13182766 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.31 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 72.07 |
TPSA : | 66.57 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.09 cm/s |
Log Po/w (iLOGP) : | 2.81 |
Log Po/w (XLOGP3) : | 3.84 |
Log Po/w (WLOGP) : | 4.06 |
Log Po/w (MLOGP) : | 2.63 |
Log Po/w (SILICOS-IT) : | 3.44 |
Consensus Log Po/w : | 3.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.93 |
Solubility : | 0.0291 mg/ml ; 0.000117 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.93 |
Solubility : | 0.0029 mg/ml ; 0.0000116 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.3 |
Solubility : | 0.0125 mg/ml ; 0.0000502 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
91% | Stage #1: With trifluoroacetic acid In dichloromethane for 12 h; Stage #2: With sodium hydroxide In dichloromethane |
b; 1-Benzothiophen-2-amine[00118] To a solution of 1 ,1-Dimethylethyl 1-benzothien-2-ylcarbamate (1.0 g, 4.01 mmoles) in DCM (10 ml_) was added TFA (2.0 mL) and stirred for 12 h. The reaction mixture was concentrated, and the resulted residue was redissolved in DCM and washed with 1 N NaOH (2x50 mL), brine and dried over Na2SO4. The mixture was filtered and concentrated to afford pure product (0.54 g) in 91 percent yield. LCMS (m/z): 150.0 (M+H). |
91% | With hydrogenchloride In 1,4-dioxane at 20℃; for 2 h; | A solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1,4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91percent). HPLC-MS tR=1.5 Min(UV254 nm). Mass calculated for formula C8H7NS, M+149.21, observed LC/MS m/z 150.40 (M+H). |
91% | With hydrogenchloride In 1,4-dioxane at 20℃; for 2 h; | Example 236; A solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1,4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91percent). HPLC-MS tR=1.5 Min (UV254nm). Mass calculated for formula C8H7NS, M+ 149.21, observed LC/MS m/z 150.40 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | for 8 h; Heating / reflux | Benzo[Z>]thiophen-2-yl-carbamic acid tert-butyl ester (1-B).; A solution of compound 1-A (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in -butanol (150 mL) was heated at reflux for 8 h. The solvent was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford compound 1-B as a colorless solid (18.9 g, 94percent). 1H-NMR (DMSO-^): δ 1.50 (s, 9H), <n="183"/>6.78 (s, IH), 7.16 (d of d, IH), 7.27 (d of d, IH), 7.58 (d, IH), 7.77 (d, IH), 10.70 (br s, IH); MS: m/z 250.2 (MH+). |
94% | for 8 h; Reflux | B. Benzo[b]thiophen-2-yl-carbamic acid tert-butyl ester (1d). A solution of 2-carboxybenzo[b]thiophene (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in t-butanol (150 mL) was heated at reflux for 8 hours. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel, using dichloromethane as the eluant, to give the product as a colorless solid (18.9 g, 94percent). 1H NMR (DMSO-d6): δ 1.50 (s, 9H), 6.78 (s, 1H), 7.16 (d of d, 1H), 7.27 (d of d, 1H), 7.58 (d, 1H) and 7.77 (d, 1H), 10.70 (br s, 1H); MS: m/z 250.2 (MH+). |
94% | for 8 h; Reflux | Example 1 benzo[b]thiophen-2-yl-carbamic acid tert-butyl ester (1-B). A solution of compound 1-A (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in t-butanol (150 mL) was heated at reflux for 8 h. The solvent was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford compound 1-B as a colorless solid (18.9 g, 94percent). 1H-NMR (DMSO-d6): δ 1.50 (s, 9H), 6.78 (s, 1H), 7.16 (d of d, 1H), 7.27 (d of d, 1H), 7.58 (d, 1H), 7.77 (d, 1H), 10.70 (br s, 1H); MS: m/z 250.2 (MH+). |
64% | for 5 h; Heating / reflux | A solution of benzo[b]thiophene-2 carboxylic acid (1.25 g, 7.03 mmol), diphenylphosphoryl azide (1.94 g, 7.03 mmol) and triethylamine (0.98 mL, 7.03 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate and then concentrated to afford a beige solid. Purification by column chromatography (SiO2 DCM/Hexanes) afforded compound 235 as a white solid 0.96 g (64percent). HPLC-MS tR=2.7 Min(UV254 nm). Mass calculated for formula C13H15NO2S, M+249.33, observed LC/MS m/z 250.40 (M+H). |
64% | for 5 h; Heating / reflux | Example 235; A solution of benzo[b]thiophene-2 carboxylic acid (1.25 g, 7.03 mmol), diphenylphosphoryl azide (1.94 g, 7.03 mmol) and triethylamine (0.98 mL, 7.03 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate and then concentrated to afford a beige solid. Purification by column chromatography (SiO2 DCM/Hexanes) afforded compound 235 as a white solid 0.96 g (64percent). HPLC-MS tR=2.7 Min (UV254nm). Mass calculated for formula C13H15NO2S, M+ 249.33, observed LC/MS m/z 250.40 (M+H). |
62% | for 16 h; Heating / reflux | Example 36; Preparation of 3-(1 -benzothien-2-yl)-6-(3-fluoro-2-hvdroxyphenyl)-2-methyl-5-(2- phenylethyl)-4(3H)-pvrimidinone; [00115] a; 1 ,1-Dimethylethyl 1-benzothien-2-ylcarbamate; EPO <DP n="39"/>[00116] To a solution of i-benzothiophene-2-carboxylic acid (5.0 g, 0.028 mol) in dry NBuOH (70 ml_) was added TEA (4.3 ml_, 0.031 mol). After 5 min. of stirring, DPPA (6.67 ml_, 0.031 mol) was added and the reaction was refluxed for 16 h. The reaction was concentrated and the resulting residue was diluted with ethyl acetate and washed successively with sat. NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated before purifying by silica chromatography (0 - 40percent ethyl acetate/hexane) to afford pure product (4.35 g) in 62percent yield. 1H NMR (400 MHz, DMSO-Cf6) .pound. ppm 1.50 (s, 9 H), 6.77 (s, 1 H), 7.15 (t, J=0.85 Hz, 1 H), 7.26 (t, J=0.85 Hz, 1 H), 7.59 (d, J=7.79 Hz, 1 H), 7.76 (d, J=7.78 Hz, 1 H), 10.2 (brs, 1 H). |
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