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CAS No. : | 29684-56-8 | MDL No. : | MFCD00077815 |
Formula : | C8H18N2O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 238.30 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.94 |
TPSA : | 68.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.14 cm/s |
Log Po/w (iLOGP) : | 0.22 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 2.33 |
Log Po/w (MLOGP) : | -3.27 |
Log Po/w (SILICOS-IT) : | -1.15 |
Consensus Log Po/w : | -0.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.4 |
Solubility : | 9.55 mg/ml ; 0.0401 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.89 |
Solubility : | 3.08 mg/ml ; 0.0129 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.37 |
Solubility : | 1.01 mg/ml ; 0.00425 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.97 |
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 |
---|---|---|
63% | In benzene; at 20℃; | Methyl(carboxysulfamoyl)triethylammonium hydroxide 1 was prepared using the Organic Syntheses procedure published by Burgess et al.[2] Compound 1 was obtained as colourless crystals (mp 67.2-69.5 C, lit[2] mp 71-728C), yield 63 %. dH (600 MHz, CDCl3) 1.41 (9H, t, JHH 7.2, NCH2CH3), 3.47 (6H, q, JHH 7.2, NCH2CH3, 3.70 (3H, s, CH3), dC (151 MHz, CDCl3) 9.38 (NCH2CH3), 50.43 (NCH2CH3), 53.26 (OCH3), 158.2 (C=O). nmax (CHCl3)/cm_1 3020 (w), 2951 (w), 1698 (m), 1460 (w), 1438 (w), 1342 (w), 1262 (s), 1222 (w), 1202 (w), 1187 (w), 1110 (w), 1039 (w), 965 (w), 866 (w), 734 (w), 714 (w), 668 (w), 623 (w), 590 (w), 577 (w), 563 (w). nmax (solid)/cm_1 3046 (w), 2996 (w), 2979 (w), 2951 (w), 1719 (w), 1688 (m), 1455 (m), 1441 (m), 1402 (w), 1338 (w), 1326 (m), 1304 (w), 1241 (s), 1219 (m), 1186 (m), 1111 (m), 1092 (m), 1042 (m), 1023 (m), 960 (m), 893 (w), 856 (m), 835 (m), 787 (m), 717 (m), 695 (w), 679 (w), 668 (w), 651 (w), 641 (w), 627 (m), 600 (s), 577 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.9% | In 1,4-dioxane; at 20 - 105℃; for 1.58333h; | Step 1: (3aS,6aR)-5-Benzyl-2,2-dioxo-tetrahydro-1-oxa-2lambda6-thia-3,5-diaza-pentalene-3-carboxylic acid methyl ester To a solution of the product from Preparation 1, Step 2 (6.4 g, 33.1 mmol) in 1,4-dioxane (70 mL) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (19.7 g, 82.8 mol). After stirring at room temperature for 5 min, the solution was warmed to 105 C. and stirred at that temperature for 1.5 h. The solution was cooled to room temperature, concentrated and partitioned between EtOAc (300 mL) and H2O (100 mL). The layers were separated and the organic phase washed with saturated sodium chloride, dried over sodium sulfate and concentrated to give the cyclic sulfamate product as a syrup that solidifies upon standing (10.3 g, 61.9%). 1H NMR (400 MHz, Chloroform-d) delta 7.39-7.23 (m, 5H), 5.19-5.13 (m,1H), 4.68-4.61 (m, 1H), 3.90 (s, 3H), 3.78-3.62 (q, 2H), 3.20-3.10 (m, 2H), 2.69-2.59 (m, 2H). MS m/z 269.1 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | [0226] The amide 138 (2.7 g) was dissolved in dichloromethane and (methoxycarbonylsulfamoyl) triethylammonium hydroxide, inner salt (L. 3 g) was then added. The resulting mixture was stirred overnight, and concentrated. Purification with flash column chromatography (hexane/ethyl acetate 5: 1) gave the nitrile 139 as a white solid. 1H-NMR (CDC13, 400MHz) 6 7. 87-7. 64 (m, 6H), 7.19 (d, 2H), 5.96 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; n-heptane; ethyl acetate; | Step 10: 2-Oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-hydroxypropyl]amide (240 mg, 565 mumol) and Burgess reagent (134 mg, 565 mumol) in THF (5 mL) were heated under reflux conditions for 1 hour. The mixture was diluted with EtOAc, washed with saturated NaHCO3, brine and dried (MgSO4). Purification by chromatography (silica gel, CH2Cl2) gave the product as a yellow foam (91 mg), this was then repurified by chromatography (silica gel, 0-50% EtOAc in heptane) to give 6-[5-(4-benzylpiperidin-1-ylmethyl)-4,5-dihydrothiazol-2-yl]-3H-benzoxazol-2-one (52 mg, 23%) as an off white solid: m/z408.21 (MH+) numax 3261, 1777, 1494, 1447, 1273 cm-1 1H-NMR (CDCl3) deltaH 1.31 (4H, m, alkyl), 1.60 (3H, m, alkyl), 1.97 (2H, t, CH2, J 7.2 Hz), 2.53 (4H, 2*d, alkyl, J 6.4, 7.2 Hz), 2.90 (2H, bs, alkyl), 4.12 (1H, m, CHS), 4.35 (2H, m, CH2N), 7.03 (1H, d, arom., J 8.0 Hz), 7.13-7.30 (5H, m, Ph), 7.62 (1H, dd, arom., J 1.6, 8.0 Hz), 7.73 (1H, d, arom., J 1.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; In methanol; dichloromethane; N,N-dimethyl-formamide; | To 260 mg (0.87 mmol) of the acid above dissolved in 5 ml DMF was added 140 mg (0.85 mmol) L-phenylalaninamide [educt 2], 120 mg (0.88 mmol) of HOBT, 170 mg (0.88 mmol) of EDCI and 0.34 ml (3.06 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated to give the 388 mg of the crude product as a white solid. To the solution of 388 mg (0.87 mmol) of the crude product from above in dichloromethane (10 ml) was added <strong>[29684-56-8]Burgess Reagent</strong> 210 mg (0.88 mmol). The mixture was stirred at room temperature for overnight. After the dichloromethane was removed, the residue was dissolved in 2 ml MeOH and purified with preparative thin layer chromatography (hexane:ethyl acetate 1:1) to give the product as a white foam: 88 mg (0.21 mmol). 27.5% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; | Starting Material Synthesis Example 106 2-(5-ethyloxazol-2-yl)-4-methoxybenzo(b)furan To a solution of N-(2-oxobutyl)-4-methoxybenzo(b)furan-2-carboxamide (2.00 g) in THF (60 ml) was added Burgess reagent (7.30 g), and the mixture was stirred with refluxing. Water (200 ml) was added to the reaction mixture and the mixture was extracted with ether. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (1.56 g) as colorless crystals, melting point 88-87 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In tetrahydrofuran; ethyl acetate; | Preparation 152 ethyl (4S)-2-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-4,5-dihydro-1,3-oxazole-4-carboxylate A solution of tert-butyl (3R)-6-cyclohexyl-3-([(1S)-2-ethoxy-1-(hydroxymethyl)-2-oxoethyl]amino}carbonyl)hexanoate (preparation 151) (10.0 g, 24.2 mmol) in THF (80 ml) was treated with Burgess reagent (6.34 g, 26.6 mmol) and heated at reflux for 1 hour. The reaction mixture was allowed to cool to room temperature and stored in a fridge for 3 days. The solvent was removed under reduced pressure. The crude material was ourififed on a silica column eluding with a solvent gradient of pentane:EtOAc (100:0) gradually changing to (80:20) to afford the title compound as a colourless oil (9.26 g, 97%). 1Hnmr (CDCl3): 0.81 (2H, m), 1.10-1.35 (11H, m), 1.40 (9H, s), 1.45-1.70 (7H, m), 2.39 (1H, dd), 2.60 (1 H, dd), 2.85 (1H, m), 4.20 (2H, m), 4.30-4.45 (2H, m), 4.66 (1H, dd). MS: 396 (MH+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In ethyl acetate; benzene; | EXAMPLE 277 (E)-2-(4-Fluorophenoxy)-3-[3-(4-methoxyphenyl)-1-propenyl]-pyridine A mixture of 0.97 g (2.7 mmol) 2-(4-Fluorophenoxy)-a-[2-(4-methoxyphenyl)ethyl]-3-pyridinemethanol, 0.93 g (3.9 mmol) of <strong>[29684-56-8]Burgess Reagent</strong>, and 20 mL of benzene was heated to reflux for 4 h. The cooled mixture was partitioned between 300 mL of EtOAc and 100 mL of saturated aqueous sodium hydrogencarbonate solution, and the separated organic layer was washed with 100 mL of brine, dried (Na2SO4), and evaporated to 1.10 g of an oil. Purification by flash chromatography using 15% EtOAc-hexane as eluant gave 0.39 g (42% yield) of the title compound as an oil. 1H NMR (CDCl3) d 3.60 (2H, d, J=7 Hz), 3.82 (3H, s), 6.48 (1H, dt, J=7, 16 Hz), 6.78 (1H, d, J=16 Hz), 6.86-7.18(9H, m), 7.79 (1H, dd, J=2, 8 Hz), 7.99 (1H, dd, J=2, 5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexane; ethyl acetate; | To a solution of dl-2-[(4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-3-methyl-benzofuran-2-carbonyl)-amino]-4-cyclohexyl-3-hydroxy-butyric acid ethyl ester (40.0 mg) in tetrahydrofuran (0.5 ml) was added dropwise Burgess reagent (19 mg) in tetrahydrofuran (0.5 ml) over a period of 15 minutes at room temperature and the mixture was stirred another 25 minuets at room temperature and then heated at 90 C. for 2 hours. After cooling, the reaction mixture was directly poured onto silica gel column chromatography and eluted with 2:3 mixture of n-hexane and ethyl acetate to give dl-5-cyclohexylmethyl-2-(3-methyl-4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-trans-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester (35.7 mg). FAB-MS: m/z 634 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | To a dry mixture of 27-1 (2-methoxyphenylhydrazide, 139 mg, 0.837 mmol), 27-2 (benzoxazol-2- one-6-carboxylic acid, 150 mg, 0.837 mmol), and HATU (318 mg, 0.837 mmol) was added THF (10 mL) to yield a hazy reddish solution. DIPEA (0.29 mL, 1.67 mmol) was added and the reaction was stirred at rt for 2 hr. Burgess reagent (499 mg, 2.09 mmol) was added one portion, and the reaction was heated to 60C overnight. An additional 499 mg Burgess reagent was added. and continued heating. After 4 hr, 2N KHSO4 (10 mL) was added and the resulting oily mixture was extracted 3X EtOAc. The combined organics were washed once with water, once with brine, filtered through cotton and concentrated to an orange solid which was purified by reverse phase chromatography, 20% - 60% MeCN/water/0.1% TFA to yield 67 mg 27-3(18%) MJ-T+ = 447.0. ?H NMR (400 MHz, DMSO) 8.02 - 7.97 (3H, m), 7.74 (1H, d, J=8.4 Hz), 7.64 (1H, t, J=8.2 Hz), 7.30 (1H, d, J=8.4 Hz), 7.18 (1H, t, J=7.4 Hz), 3.95 (3H, s), 3.39 (3H, s). |
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H400 | Very toxic to aquatic life |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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