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CAS No. : | 22724-81-8 | MDL No. : | MFCD02683229 |
Formula : | C5H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ULAXUFGARZZKTK-YFKPBYRVSA-N |
M.W : | 103.16 | Pubchem ID : | 6951248 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 30.02 |
TPSA : | 46.25 Ų |
GI absorption : | High |
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) : | -6.99 cm/s |
Log Po/w (iLOGP) : | 1.54 |
Log Po/w (XLOGP3) : | -0.08 |
Log Po/w (WLOGP) : | 0.11 |
Log Po/w (MLOGP) : | 0.23 |
Log Po/w (SILICOS-IT) : | -0.04 |
Consensus Log Po/w : | 0.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.23 |
Solubility : | 60.6 mg/ml ; 0.587 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.44 |
Solubility : | 37.5 mg/ml ; 0.364 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.52 |
Solubility : | 31.0 mg/ml ; 0.301 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.11 |
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 |
---|---|---|
79% | HbO (25 mL) at room temperature and BOC2O (15.1 g, 69.2 mmol) was added to produce an opaque suspension that was stirred vigorously for 2 h at room temperature. THF was removed in vacuo, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgStheta4 and concentrated in vacuo. Chromatography on Sitheta2 (3/1 Hex/EtOAC) afforded 18.5 g (79%) of Compound 31 as a colorless oil (LC/MS m/z 293.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A Tetrahydro-3(S)-propyl-(2H)-1,4-thiazepine-5-thione The title compound was prepared employing the procedure in Example 17, Steps A to E and starting from <strong>[22724-81-8]L-norvalinol</strong> instead of (+-)-trans-2-aminocyclohexanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Specific examples of the amine derivative of formula (IA-2) are as follows: (2S)-2-aminobutanol, (2S)-2-amino-3-methylbutanol, (2S)-2-aminopentanol, (2S)-2-amino-4-methylpentanol, (2S)-2-aminohexanol, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Step A: To an ice cold, stirred suspension of NaH (60% in oil, 1.9 g, 46.0 mmol) in toluene (62 mL) was added dropwise a solution of <strong>[22724-81-8](S)-2-aminopentan-1-ol</strong> (2.1 g, 20.0 mmol) in toluene (44 mL). After the addition was completed, the reaction mixture was warmed to room temperature and a solution of ethyl chloroacetate (2.7 g, 22.0 mmol) in toluene (12 mL) was added in a dropwise manner. The resulting mixture was then stirred at reflux for 20 h, cooled to room temperature, and solid ammonium chloride (2.5 g, 46.0 mmol) was added to the reaction. The mixture was stirred for 20 min and then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 98:2 CH2Cl2/CH3OH to 95:5 CH2Cl2/CH3OH) to give (S)-5-propylmorpholin-3-one (2.2 g, 76%) as a yellow oil. To ice-cold THF (10 mL) was added lithium aluminum hydride (1.0 M solution in THF, 30 mL, 30 mmol). Once the addition was complete, a solution of (S)-5-propylmorpholin-3-one (2.2 g, 15 mmol) in THF (10 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 20 h. The reaction was cooled in an ice-bath and to this was slowly added H2O (1.2 mL), then 15% aqueous solution of sodium hydroxide (1.2 mL), and then H2O (1.2 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with EtOAc (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (S)-3-propylmorpholine (1.9 g, 98%) as a light yellow oil. 1H NMR and MS consistent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-pyrrolidin-2-one; at 140℃; for 50h; | (iv) (S)-2-(4-((2-Ammo-4-(l-hydroxypentan-2-ylammo)-6-methylpyrimidin-5- yl)methyl)-3-methoxyphenyl)acetonitrile(S)-2-Aminopentan-l-ol (0.136g) was added to a solution of the product from step (iii) in NMP (2mL) . The resulting mixture was stirred at 1400C for 5Oh then diluted with EtOAc and washed with saturated NaHCO3 solution and saturated brine. The organic phase was dried, filtered and evaporated. The crude product was purified by column chromatography, elution gradient 5 to 10% MeOH in DCM to give the subtitle compound, 0.095g.1H NMR DMSO-J6: delta 6.98 (IH, s), 6.84 - 6.78 (2H, m), 4.62 (IH, t), 4.21 - 4.12 (IH, m),3.97 (2H, s), 3.86 (3H, s), 3.65 (2H, s), 3.41 - 3.33 (2H, m), 2.06 (3H, s), 1.55 - 1.41 (IH, m), 1.35 - 1.21 (IH, m), 1.15 - 1.00 (2H, m), 0.78 (3H, t) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; at 160 - 180℃; for 1.5 - 2h;Microwave irradiation;Product distribution / selectivity; | (i) (S)-2-(4-((2-Amino-4-(l-hydroxypentan-2-ylamino)-6-methylpyrimidin-5- yl)methyl)phenyl)acetonitrileTo the product from example 41 step (iv) (300mg) in butanol (2ml), (S)-(+)-2-amino-l- pentanol (213mg) was added and the reaction mixture heated in a microwave, at 1800C for 2h. The solvent was evaporated under reduced pressure and the crude product was purified using chromatography, to give the subtitle compound, 150mg.1H NMR DMSO d-6: delta 7.26 (, 2H), 7.20 - 7.15 (m, 2H), 6.74 (s, 2H), 6.29 (s, IH), 4.67 (t, IH), 4.25 - 4.16 (m, IH), 3.95 (s, 2H), 3.87 (d, IH), 3.79 (d, IH), 3.44 - 3.33 (m, 2H), 2.17 (s, 3H), 1.56 - 1.46 (m, IH), 1.40 - 1.28 (m, IH), 1.12 - 1.00 (m, 2H), 0.78 (t, 3H) LC-MS m/z 340 ESI; (ii) (S)-2-(4-((2-Amino-4-(l-hydroxypentan-2-ylamino)-6-methylpyrimidin-5- yl)methyl)phenyl)acetic acid To the product of step (i) (0.4g) in butan-1-ol (3ml), (S)-(+)-2-amino-l-pentanol (0.5g) was added and the reaction heated in a microwave, at 16O0C at IOOW for 1.5h. After cooling, aq. 5M KOH (ImI) was added and the mixture heated at 1000C for 48h. The <n="139"/>mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by RPHPLC to give the TFA salt, which was purified by SCX, eluting with MeCN then 10%aq NH3ZMeCN to give the subtitle compound, 174mg. LC-MS m/z APCI +372 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; at 160℃; for 2h;Microwave irradiation; | (vi) (S)-2-(3-((2-Ammo-4-(l-hydroxypentan-2-ylammo)-6-methylpyrimidin-5- yl)methyl)-4-methoxyphenyl)acetic acid (S)-(+)-2-Amino-l-pentanol (lOOmg) was added to a suspension of the product from step (v) (243mg) in butan-1-ol (2mL). The reaction was heated in a microwave at 1600C for 2h. 5M KOH (0.5mL) was added and the mixture heated in a microwave at 100 0C for Ih. The solvent was evaporated under reduced pressure and the residue purified by RPHPLC to give the subtitle compound as a white solid, 60mg. LC-MS m/z 389 APCI + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | (5)-2-amino-l-pentanol (1.00 g, 9.7 mmol) was dissolved in ethylformate (7.84 ml, 7.19 g, 97 mmol). This reaction mixture was refluxed at 80 C for 4 hours, followed by stirring overnight at room temperature. The colourless solution was concentrated in vacuo and stirred for 1 hour in a 10 mol% K2C03 in MeOH (25 ml). Afterwards, the pH was set to 7 with DOWEX 50wx8, followed by filtration and concentration in vacuo to give 12 (1.26 g, 9.61 mmol, 99%). [a f = -29.6 (c = 1.15, CHCI3); H NMR (250.13 MHz, CDC13): delta = 8.20 (s, 1H), 5.81 (bs, 1H), 4.04 (m, 1H), 2.11 (b, 1H), 1.47 (m, 4H), 0.94 (t, J = 7.0 Hz, 3H); 13C NMR (62.90 MHz, CDCI3): 161.8 (C), 65.1 (CH2), 50.6 (CH), 33.2 (CH2), 19.2 (CH2), 13.9 (CH3); IR (neat): vmax (cm ) = 3248 (s), 2957 (m), 1651 (s), 1528 (m), 1381 (m); HRMS (ESI, 4500 V): m/z calcd. for C6Hi3N02Na+ ([M + Na]+) 154.0838, found 154.0835. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-pyrrolidin-2-one; at 120℃; for 60h;Product distribution / selectivity; | (iS)-2-Aminopentan-l-ol (0.769 g) was added to a solution of the product from Example 12 step (iii) (1.2 g) in NMP (20 mL) and the mixture was stirred at 1200C for 60 h. The reaction mixture was then cooled, diluted with EtOAc (50 mL), washed with saturated NaHCO3 (2 x 50 mL), brine (50 mL), dried and concentrated by evaporation. The crude product was purified by FCC eluting with 20: 1 to 10:1 DCM-MeOH to produce an orange oil (0.475 g). A 100 mg sample was further purified by RPHPLC to give the title compound as an orange gum (15 mg); 1H NMR: 7.48 (d, IH), 7.46 (dd, IH), 6.89 (d, IH), 5.68 (s, 2H), 5.50 (d, IH), 4.58-4.48 (m, IH), 4.17-4.05 (m, IH), 3.92 (s, 3H), 3.84 (s, 3H), 3.70 (s, 2H), 3.39-3.20 (m, 2H), 1.99 (s, 3H), 1.54-1.39 (m, IH), 1.33-1.20 (m, IH), 1.16- 1.02 (m, 2H), 0.76 (t, 3H); LC-MS m/z 389. | |
In 1,4-dioxane; at 170℃; for 9h;Microwave irradiation; | (iv) Methyl 4- [(2-amino-4- { (2S)- 1 -hydroxypentan-2-yl] amino I -6-methylpyrimidin-5 - vDmethyll -3 -methoxybenzo ate(5)-2-Aminopentan-l-ol (0.481 g) was added to a suspension of methyl 4-[(2-amino-4- chloro-6-methylpyrimidin-5-yl)methyl]-3-methoxybenzoate (0.5 g) in dioxane (5 mL). The mixture was heated in a CEM Discover microwave at 170C for 9h. The mixture was then cooled and concentrated in vacuo. Purification by FCC, eluting with 5% CH3OH in CH2CI2 gave the sub-title compound (0.25 g) as a orange gum; 1H NMR: 7.53-7.42 (m, 2H), 6.89 (d, 1H), 5.75 (d, 2H), 5.58 (d, 1H), 4.61-4.54 (m, 1H), 4.17-4.08 (m, 1H), 3.92 (s, 3H), 3.83 (s, 3H), 3.69 (d, 2H), 3.28-3.23 (m, 1H), 2.00 (d, 3H), 1.53-1.40 (m, 1H), 1.35-1.19 (m, 2H), 1.16-1.02 (m, 2H), 0.77 (t, 3H); LC-MS: m/z 389. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chiral stationary phase including isopropyl-functionalized CF6; In methanol; acetic acid; triethylamine; acetonitrile; at 20℃;Purification / work up; | In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the "dead time" to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In water; tert-butyl alcohol; at 70℃;Inert atmosphere; | [0041] Example D. Synthesis of (2S)-2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7- yljmethyl) amino] pentan-l-ol (D.l). (0069) (0070) D.1 (0071) [0042] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]pentan-l- ol (D.l). (25)-2-Aminopentan-l-ol (0.050 g, 0.48 mmol), <strong>[2227-98-7]9-<strong>[2227-98-7]deazaadenine</strong></strong> (0.065 g, 0.48 mmol) and aq. formaldehyde solution (37%, 0.044 mL, 0.59 mmol) were stirred in tert- butanol (2 mL) at 70 C overnight. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (CHCI3-7M NH3/MeOH, 9: 1 then 85: 15) to afford D.l as a colourless solid (0.073 g, 60%). XH NMR (500 MHz, CD3OD):5 8.16 (s, 1H), 7.47 (s, 1H), 3.99 (d, J = 13.7 Hz, 1H), 3.96 (d, J = 13.7 Hz, 1H), 3.66 (dd, J= 11.3, 4.4 Hz, 1H), 3.48 (dd, J= 11.3, 6.6 Hz, 1H), 2.69 (m, 1H), 1.54-1.30 (m, 4H), 0.89 (t, J= 7.2 Hz, 3H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.8 (CH), 146.6 (C), 128.9 (CH), 115.4 (C), 114.7 (C), 62.3 (CH2), 59.2 (CH), 41.1 (CH2), 34.3 (CH2), 20.3 (CH2), 14.6 (CH3). ESI-HRMS calcd for Ci2H20N5O+, (M+H)+, 250.1663, found 250.1663. |
Tags: 22724-81-8 synthesis path| 22724-81-8 SDS| 22724-81-8 COA| 22724-81-8 purity| 22724-81-8 application| 22724-81-8 NMR| 22724-81-8 COA| 22724-81-8 structure
[ 53448-09-2 ]
(R)-2-Amino-4-methylpentan-1-ol
Similarity: 0.90
[ 7533-40-6 ]
(S)-2-Amino-4-methylpentan-1-ol
Similarity: 0.90
[ 24629-25-2 ]
(2S,3S)-2-Amino-3-methylpentan-1-ol
Similarity: 0.86
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P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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