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CAS No. : | 952182-03-5 | MDL No. : | MFCD08544349 |
Formula : | C4H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JUIXJPRSYHSLHK-UHFFFAOYSA-N |
M.W : | 87.12 | Pubchem ID : | 46839993 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 23.11 |
TPSA : | 21.26 Ų |
GI absorption : | Low |
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) : | -7.19 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | -0.51 |
Log Po/w (WLOGP) : | -0.4 |
Log Po/w (MLOGP) : | -0.57 |
Log Po/w (SILICOS-IT) : | 0.59 |
Consensus Log Po/w : | 0.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.01 |
Solubility : | 88.6 mg/ml ; 1.02 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.53 |
Solubility : | 296.0 mg/ml ; 3.4 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.56 |
Solubility : | 24.3 mg/ml ; 0.279 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 | UN#: | 1993 |
Hazard Statements: | H226-H302-H315-H318-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
In dichloromethane; at 0 - 20℃; | The 2-methylpropanal (0.5 mL, 5.48 mmol) was stirred in DCM (10 mL) while being cooled with an ice bath. Bromine (0.31 mL, 6.03 mmol) was slowly added via addition funnel over a 15 min period. After 1 h of stirring at 0 C, the reaction was concentrated to a light yellow liquid. This was redissolved in DCM (5 mL) and cooled with an ice bath while the N- methyloxetan-3-amine (0.49 mL, 5.48 mmol) was slowly added (diluted with 5-10 mL of DCM) over a 10 minute period. Then the cooling bath was removed and the reaction mixture was stirred at room temperature overnight. The mixture was washed with brine, then the remaining DCM layer was washed by 0.5N HC1. The combined aq. layer was adjusted with KOH to pH 10- 1 1 , extracted with CH2CI2, and the combined organic layer was washed with brine and dried by Na2S04, filtered and concentrated to collect 2-methyl-2-[methyl(oxetan-3- yl)amino]propanal as a light yellow liquid. The crude material was used in the next step directly without further purification. | |
200 mg | With triethylamine; In dichloromethane; at 0℃; for 3h; | A solution of 2-bromo-2-methylpropanal (1 g, 6.7 mmol), <strong>[952182-03-5]N-methyloxetan-3-amine</strong> (250 mg, 2.87 mmol) and Et3N (1.35 g, 13.4 mmol) in DCM (10 mL) at 0 C was stirred for 3 h. The solvent was removed to give a residue, which was purified by S1O2 chromatography eluting with PE:EtOAc (1 : 1 ) to afford 2-methyl-2-(methyl(oxetan-3-yl)amino)propanal (200 mg, 44.4%) as a oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.11 g | In formic acid; water; at 65℃; for 4h; | Oxetan-3-yl-methylamine (0.25 g, 2.87 mmol) was dissolved in a mixture of formaldehyde (37% solution in water; 1 mL) and formic acid (1 mL) then heated at 65 C. for 4 hours The reaction mixture was poured into aqueous sodium hydroxide/brine and extracted with Et2O. The organic layer was dried over MgSO4, filtered and carefully concentrated in vacuo to afford the title compound as a residue still containing traces of Et2O (0.11 g). 1H NMR (300 MHz, CDCl3): delta 4.80 (2H, m), 4.38-4.45 (2H, m), 3.09-3.28 (1H, m), 2.62 (2H, d, J=7.4 Hz), 2.20 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Example 237 Rac-(4bS,5R,6R,7S,7aR)-7a-(4-bromophenyl)-4b,5-dihydroxy-4-methoxy-N-methyl-N-(oxetan-3-yl)-7-phenyl-4b,6,7,7a-tetrahydro-5H-cyclopenta[4,5]furo[2,3-c]pyridine-6-carboxamide (Cpd. No. 237F) (1483) Synthesis of rac-(4bS,5R,6R,7S,7aR)-7a-(4-bromophenyl)-4b,5-dihydroxy-4-methoxy-N-methyl-N-(oxetan-3-yl)-7-phenyl-4b,6,7,7a-tetrahydro-5H-cyclopenta[4,5]furo[2,3-c]pyridine-6-carboxamide (Cpd. No. 237F) (1484) To a solution of 801 rac-(4bS,5R,6R,7S,7aR)-7a-(4-bromophenyl)-4b,5-dihydroxy-4-methoxy-7-phenyl-4b,6,7,7a-tetrahydro-5H-cyclopenta[4,5]furo[2,3-c]pyridine-6-carboxylic acid (1, 1.0 g, 2.0 mmol) in 79 N,N-dimethylformamide (10 mL), 1992 O-(7-Azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate (2.29 g, 6.0 mmol) and 49 N,N-diisopropylethylamine (1.80 ml, 10.0 mmol) were added at 0 C. and stirred the mixture for 5 min. 1993 <strong>[952182-03-5]N-methyloxetan-3-amine</strong> (2, 1.44 g, 5.0 mmol) was then added and the reaction mixture was stirred for 2 h at room temperature. After completion, reaction mixture was diluted with ethyl acetate and washed with cold water. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by combi-flash (12 g, RediSep column) using 6% 6 methanol in 26 dichloromethane as eluent. The desired fractions were concentrated to afford 1994 rac-(4bS,5R,6R,7S,7aR)-7a-(4-bromophenyl)-4b,5-dihydroxy-4-methoxy-N-methyl-N-(oxetan-3-yl)-7-phenyl-4b,6,7,7a-tetrahydro-5H-cyclopenta[4,5]furo[2,3-c]pyridine-6-carboxamide (Cpd. No. 237F) as white solid. Yield: 0.94 g, 83%; MS (ESI) m/z 567.25[M+1]+. 1H NMR (400 MHz, DMSO-d6) delta 8.10 (s, 1H), 7.99 (s, 1H), 7.22-7.20 (m, 2H), 7.12-7.07 (m, 2H), 7.04-7.01 (m, 2H), 6.96-6.86 (m, 3H), 5.71 (d, J=11.3 Hz, 1H), 5.24 (d, J=5.3 Hz, 1H), 5.09-5.06 (m, 1H), 4.97-4.75 (m, 2H), 4.63-4.53 (m, 3H), 4.36 (d, J=13.6 Hz, 1H), 4.25-4.20 (m, 1H), 3.87 (s, 3H), 3.43 (s, 2H), 2.96 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | N-(6-fluoro-3'-formyl-4-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)-[l,r- biphenyl] -3 -yl)-4-(trifluoromethyl)-6-(2-(trimethylsilyl)ethoxy Nicotinamide (40 mg, 0.063 mmol), <strong>[952182-03-5]N-methyl-3-oxetanamine</strong> (11.05 mg, 0.127 mmol) and acetic acid, glacial, 99.8% (15.23 mg, 0.254 mmol) were mixed in anhydrous DCE. A cloudy solution was obtained. After 5-10 min, sodium triacetoxyborohydride (40.3 mg, 0.190 mmol) was added and the reaction mixture was stirred at RT. There was no difference observed between 7.5h and overnight at RT. A small amount of the starting material (approx. 5%) of the starting material was observed along with the desired product. The reaction mixture was quenched with sat aq NaHCCb solution (basic). The organic phase was separated, the aqueous phase was extracted with DCM (x2), then the combined organic phase was washed with brine, dried over Na2S04 and concentrated to obtain the crude product. It was purified on reverse phase isco column (5.5G), eluting with water containing 0-60 % acetonitrile. The appropriate fractions were combined and concentrated to afford the desired product as a white foam (31 mg, 70% yield). LCMS [M+H]+ = 700.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 24h;Reflux; | A flask was charged with ethyl 8-bromo-4-chloroquinoline-3-carboxylate (1.26 g, 4 mmol)(Zask, al. Bioorganic and Medicinal Chemistry Letters, 2003 , 1487 - 1490; Laxmikant, al.US2O1 3/210844), 1 -methyl-3-oxetanamine (0.42 g, 4 mmol), N,N-diisopropyl-ethylamin (0.62g, 4.8 mmol) in 40 mL Acetonitril. The reaction mixture was refluxed for 24 hours. Then thesolvent was removed under reduced pressure and the remaining material was dissolved in ethyl acetate and washed twice with water. The organic phase was separated, dried over calcium sulfate, filtered and the filtrate was removed under reduced pressure. The resulting residue was purified by reverse phase column chromatography (eluent water / acetonitrilegradient).Yield: 1.2 g (3.2 mmol, 82% of th.)1H-NMR (400 MHz, DMSO-d6) 68.94 (s, 1H), 8.20 (d, 1H), 8.14 (d, 1H), 7.55 (dd, 1H), 4.72-4.62 (m, 5H, oxetanyl), 4.43-4.38 (q, 2H), 3.10 (s, 3H), 1.37 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | General procedure: Acid SM-IX (56.9 mg, 0.17 mmcl, 100 mol-%) was dissolved in dry DCM (2 ml). Oxetane-3-amine hydrochloride (30 mg, 0.26 mmol, 150 mmol%), N-methylmorpholino (57 il, 0.52 mmol, 300 mol-%) and HOBt (40 mg,0.30 mmol, 170 mol-%) were added to the reaction mixture, stirred for 5minutes and then cooled with icebath. EDCI (73 mg, 0.38 mmol, 220 mol-%)was added and allowed to warm at room temperature. After stirring overnight, the reaction mixture was diluted with DCM, washed with 1 N HCI-solution (3 x 10 ml), water (3 x 10 ml) and finally with brine (3 x 10 ml). Dried with sodium sulphate. The solvent was evaporated and the crude product was purified bychromatography producing the compound 9 in 59% yield.1H-NMR (200 MHz, CDCI3): 1.05 (5, 3 H), 1.45 - 2.49 (m, 16 H),2.71 - 3.06 (m, 2 H), 4.50 (t, 2H), 4.95 (t, 2H), 5.06 (t, 1 H), 6.02 (m, 1 H), 6.84-6.92 (m, 1 H), 7.05 - 7.18 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Acid SM-IX (56.9 mg, 0.17 mmcl, 100 mol-%) was dissolved in dry DCM (2 ml). Oxetane-3-amine hydrochloride (30 mg, 0.26 mmol, 150 mmol%), N-methylmorpholino (57 il, 0.52 mmol, 300 mol-%) and HOBt (40 mg,0.30 mmol, 170 mol-%) were added to the reaction mixture, stirred for 5minutes and then cooled with icebath. EDCI (73 mg, 0.38 mmol, 220 mol-%)was added and allowed to warm at room temperature. After stirring overnight, the reaction mixture was diluted with DCM, washed with 1 N HCI-solution (3 x 10 ml), water (3 x 10 ml) and finally with brine (3 x 10 ml). Dried with sodium sulphate. The solvent was evaporated and the crude product was purified bychromatography producing the compound 9 in 59% yield.1H-NMR (200 MHz, CDCI3): 1.05 (5, 3 H), 1.45 - 2.49 (m, 16 H),2.71 - 3.06 (m, 2 H), 4.50 (t, 2H), 4.95 (t, 2H), 5.06 (t, 1 H), 6.02 (m, 1 H), 6.84-6.92 (m, 1 H), 7.05 - 7.18 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With triethylamine; In ethanol; at 110℃; for 17h;Inert atmosphere; | General procedure: To a solution of 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4-yl]methyl]pyridazin-3- one (building block A, 50 mg, 0.158 mmol) in EtOH (5 mL) was added under an atmosphere of argon triethylamine (0.219 mL, 1.58 mmol) and N-methylcyclopropanamine oxalate (254 mg, 1.58 mmol). The vial was capped and heated to 1 10 C for 17 h. The reaction mixture was diluted with EtOAc (20 mL) and was washed with water (15 mL) and brine (15 mL). The aqueous layers were extracted twice with EtOAc (20 mL). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography (silica, gradient: 0% to 10% MeOH in CH2Cb) afforded the title compound (40 mg, 68%) as a light brown gum. MS (ESI): 352.2 ([M+H]+). |
[ 27646-80-6 ]
2-Methyl-2-(methylamino)propan-1-ol
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