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CAS No. : | 4318-37-0 | MDL No. : | MFCD00059810 |
Formula : | C6H14N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FXHRAKUEZPSMLJ-UHFFFAOYSA-N |
M.W : | 114.19 | Pubchem ID : | 228349 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.37 |
TPSA : | 15.27 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) : | -7.28 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | -0.4 |
Log Po/w (WLOGP) : | -0.85 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 0.84 |
Consensus Log Po/w : | 0.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.3 |
Solubility : | 57.8 mg/ml ; 0.506 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.54 |
Solubility : | 399.0 mg/ml ; 3.49 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.99 |
Solubility : | 11.8 mg/ml ; 0.103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Danger | Class: | 8,3 |
Precautionary Statements: | P501-P270-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338-P310-P403+P235-P405 | UN#: | 2920 |
Hazard Statements: | H302-H314-H225 | Packing Group: | Ⅱ |
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 |
---|---|---|
62.4% | With sodium hydroxide; In water; at 0 - 20℃; for 72h;Inert atmosphere; Sealed tube; | The NaOH (0.795 g, 20 mmol) in 10 mL was added dropwise toan aqueous solution of 2-picolylchloride hydrochloride (1.64 g,10 mmol) in another 10 mL at 0 C. 1-methyl homopiperazine(1.14 g, 10 mmol) in 20 mL of water was then added to this mixtureover 15 min. The mixture was stirred in a loosely sealed flask at room temperature for three days. The reaction mixture was thenextracted with CHCl3 (3 50 mL). The organic layer was washedwith saturated sodium hydrogen carbonate solution, evaporated,and then dried (Na2SO4). The organic solvent was removed on arotary evaporator to yield the crude product as a pale-yellow oil.The pure product was obtained by extracting the oil once againwith ethyl acetate. Yield, 1.287 g (62.4%). 1H NMR (300 MHz,CDCl3),delta, 8.4 (d, 1H, J = 4.03 Hz), 7.5 (t, 1H, J = 7.66 Hz), 7.3 (d,1H,J = 7.78 Hz), 7.0 (t, 1H, J = 7.55 Hz), 3.7 (s, 2H), 2.7-2.6 (m, 4H),2.6-2.5 (m, 4H), 2.2 (s, 3H), 1.7 (pentet, 2H, J = 11.77 Hz). 13CNMR (CDCl3), delta, 46.15 (CH3), 26.51, 53.62, 54.34, 56.21, 57.40,64.75, (CH2), 121.80, 122.85, 136.27, 146.87, 159.32 ppm (ArC).ESI-MS (m/z): [M + H]+, 206.23. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethyl acetate; | 3.24a 1-(5-bromo-pyridin-2-yl)-4-methyl-[1,4]diazepan 1.5 g (5.29 mmol) 5-bromo-2-iodobenzene and 1.5 mL (11.7 mmol) <strong>[4318-37-0]1-methylhomopiperazine</strong> are heated to 170 C. for 1.5 h. After the reaction mixture has cooled 40 mL semisaturated NaHCO3 solution and 100 mL EtOAc are added. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 85:15:1). Yield: 1.10 g (77.1% of theory). C11H16BrN3 (M=270.174). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; In ISOPROPYLAMIDE; at 65℃; for 1h; | 4-methyl[l ,4]diazepam (2.8 mmol, 0.35mL) and TEA (1.30 mL, 9.3 mmol) were added to a solution of ethyl 7-chloro-6-fluoro-4-oxo-l-(4-trifluoromethylbenzyl)-l,4- dihydro-[l,8]naphthyridine-3-carboxylate (1.0 g, 2.33 mmol) in DMA (20 mL) and the mixture was heated at 65C for 1 hour. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and water. The aqueous layer was brought to pH 10 and extracted with methylene chloride. The combined organic layers were dried and <n="94"/>concentrated to give ethyl 6-fluoro-7-(4-methyl[l,4]diazepam-l-yl)-4-oxo-l -(4-trifluoro- methylbenzyl)l,4-dihydro[l,8]naphthyridine-3-carboxylate (1.15 g, 97%) as a nearly pure crude oil. LCMS: (MH+) =506.9; (MH-) =505.4; (M+23) = 529.3; actual = 506.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | 4-nuitrophenylchloroformate (111 mg, 0.55 mmol) was added to a stirred solution of 4- (2-methyl-3-propan-2-yl-imidazol-4-yl)-N-(4-piperidinyl)pyrimidin-2-amine (Example 2; 151 mg, 0.5 mmol) and TEA (0.15 ml, 1.10 mmol) in dioxane (5 ml) under an inert atmosphere. After 2 hrs N-methylhomopiperazine (0.069 g, 0.6 mmol) was added and the reaction heated at 80C for 4 hrs. After which the mixture was evaporated in vacuo and the residue dissolved in EtOAc (10 ml) and washed with IN NaOH (5 x 10 ml), then brine. The organic layer was dried, filtered and evaporated to a give a solid. The residue was loaded onto a SCX-2 column, washed with water, MeOH and then 3.5nu NH3 / MeOH to give the title compound as a yellow <n="55"/>solid (78 tng, 35%). NMR (CDCl3, 400 MHz) 1.44-1.58 (m, 8H), 1.87-1.96 (m, 2H), 2.08 (d, 2H), 2.36 (s, 3H), 2.52-2.60 (m, 5H), 2.62-2.70 (m, 2H), 2.88 (t, 2H), 3.42-3.52 (m, 4H), 3.60 (d, 2H), 3.89-4.02 (m, IH), 4.98 (brd, IH), 5.51-5.67 (appbrs, IH), 6.74 (d, IH), 7.31 (s, IH), 8.20 (d, IH); MH+ 441. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To the crude 6-[6-(lH-indol-2-yl)pyrazin-2-yl]amino}nicotinic acid (Intermediate 44)(30 mg) in MeCN (1.5 niL) were added dry NEt3 (29 muL, 0.21 mmol) and 2,4,6- tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (50% in EtOAc, 0.12 niL, 0.21 mmol). The mixture was stirred for 3 minutes after which 1- methyl- 1,4-diazepane (16 mg, 0.14 mmol) was added, and the reaction mixture was heated at 60 0C for 1 h. The material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10, MeCN). The title compound was obtained as a brown solid (8 mg). HPLC 100%(System A), 100%(System B). IH NMR (400 MHz, MeOD). Dppm 1.86 - 2.05 (m, 2 H) 2.32 - 2.46 (m, 3 H)2.60 - 2.74 (m, 3 H) 2.77 - 2.87 (m, 1 H) 3.59 - 3.71 (m, 2 H) 3.71 - 3.86 (m, 2 H) 7.01 - 7.08 (m, 1 H) 7.14 - 7.22 (m, 2 H) 7.47 (d, J=8.28 Hz, 1 H) 7.60 (d, J=7.78 Hz, 1 H) 7.74 - 7.80 (m, 1 H) 7.81 - 7.87 (m, 1 H) 8.36 - 8.44 (m, 1 H)8.61 (s, 1 H) 8.91 (s, 1 H) .MS (ESI+) calcd for C24H25N7O 427.2121 , found 427.2122. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; for 2h; | 6-Chloronicotinoyl chloride (1.00 g, 5.68 mmol) in dry DCM (4 mL) was added dropwise to an ice cold solution of 1 -methyl- 1,4-diazepane (648 mg, 5.68 mmol) and NEt3 (1.18 mL, 8.52 mmol) in dry DCM (16 mL). The mixture was allowed to attain rt and stirred for 2 hours. Saturated aq Na2CO3/water (1 : 1, 40 mL) was added and the mixture was extracted with DCM (2x 30 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to1.33 g of a light brown oil. MS (ESI+) for C12H 16C1N3O m/z 254 (M+H)+. Part of the material (294 mg, 1.16 mmol) was added to 6-chloropyrazin-2-amine (150 mg, 1.16 mmol), palladiumacetate (13 mg, 0.06 mmol), (+/-)-BINAP (36 mg, 0.06) and K2CO3 (2.4O g, 17.4 mmol) in dry toluene (12 mL) and stirred at 120 0C for 1.5 hours. The solvent was evaporated and the crude material was extracted with water/brine (1 : 1; 50 mL) and EtOAc (2x 50 mL). The organic layers were combined and concentrated. The title compound was obtained after purification by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10, MeCN), as a light brown solid (55 mg). MS (ESI+) for C16H19C1N6O m/z 347 (M+H)+.HPLC 92%(System A), 85%(System B). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 5h; | 4-({lH-Indol-2-yl]pyrazin-2-yl}amino)-3-methoxybenzoic acid (15.1 mg, 0.04 mmol), 1 -methyl- 1,4-diazepane (14.3 mg, 0.13 mmol), TBTU (40.3 mg, 0.13 mmol) and TEA (17.0 muL, 0.13 mmol) in DMF (1 mL) were shaken at ambient <n="184"/>temperature for 5h and purified using preparative HPLC system E. Yield 6.2 mg (34%). HPLC 100%, Rtau: 1.845 (10-97% MeCN over 3min). IH NMR (400 MHz, MeOD) D ppm 2.05 (s, 2 H) 2.40 - 2.69 (m, 3 H) 2.88 (s, 3 H) 3.06 (s, 1 H) 3.63 - 3.91 (m, 4 H) 4.00 (s, 3 H) 7.07 (t, J=7.40 Hz, 1 H) 7.13 - 7.28 (m, 4 H) 7.50 (d, J=8.03 Hz, 1 H) 7.62 (d, J=7.28 Hz, 1 H) 8.20 (s, 1 H) 8.48 (s, 1 H) 8.66 (d, J=8.28 Hz, 1 H). MS 457 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h; | 4-[5-(5-Fluoro-l//-indol-2-yl)pyridin-3-yl]amino}benzoic acid 10.0 mg (0.03 mmol), TBTU (46.2 mg, 0.14 mmol), TEA (19.0 muL, 0.14 mmol) and 1-methyl- 1,4-diazepane (16.4 mg, 0.14 mmol) in DMF (1 mL) were shaken at ambient temperature for 3h and purified using preparative HPLC system A. Yield 2.7 mg (21%). HPLC 100%, Rtau: 1.54 (10-97% MeCN over 3min). MS 444 (M+H)+. MS (electronspray) M+H+ m/z calcd 443.2121 found 443.2120. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.4% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In dichloromethane; at 20℃; for 7h; | [249] Example 116 : Preparation of l-ethyl-l-methyl-4-palmitoyl-l,4-diazepan-l-ium iodide according to Reaction Scheme 3; [250] 1. Preparation of l-(4-methyl-1.4-diazepan-l-yl)hexadecan-l-one; [251][252] <strong>[4318-37-0]1-methylhomopiperazine</strong> (0.9 D, 7.54 mmol), l-ethyl-3-[3-dimethylaminopropyl] carbodiimide hydrochloride (1.4 g, 7.54 mmol), and 4-dimethylaminopyridine (0.2 g, 1.74 mmol) were added to a 0.1 M methylene chloride solution of palmitic acid ( 1.5 g, 5.80 mmol) under stirring and anhydrous conditions, and stirred at room temperature for 7 hours. The produced mixture was diluted with chloroform, washed with the saturated ammonium chloride solution three times, and then with the saturated brine solution. Then, the organic layer was dried over magnesium sulfate, and distilled off under reduced pressure. The resulting primary compound was purified by a silica gel column chromatography (eluent: 5% methanol/chloroform) to obtain the target compound in 92.4% yield (1.89 g).[253] 1H-NMR (300MHz, DMSO) delta 3.48-3.41 (m, 4H), 2.45-2.40(m, 4H), 2.28-2.22 (m, 5H), 1.81-1.71(m, 2H), 1.47(br s, 2H), 1.24(br s, 24H), 0.85(t, 3H, J=6.3 Hz) |
92.4% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 7h; | Example 116; Preparation of 1-ethyl-1-methyl-4-palmitoyl-1,4-diazepan-1-ium iodide according to Reaction Scheme 3; 1. Preparation of 1-(4-methyl-1,4-diazepan-1-yl)hexadecan-1-one; <strong>[4318-37-0]1-methylhomopiperazine</strong> (0.9, 7.54 mmol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (1.4 g, 7.54 mmol), and 4-dimethylaminopyridine (0.2 g, 1.74 mmol) were added to a 0.1 M methylene chloride solution of palmitic acid (1.5 g, 5.80 mmol) under stirring and anhydrous conditions, and stirred at room temperature for 7 hours. The produced mixture was diluted with chloroform, washed with the saturated ammonium chloride solution three times, and then with the saturated brine solution. Then, the organic layer was dried over magnesium sulfate, and distilled off under reduced pressure. The resulting primary compound was purified by a silica gel column chromatography (eluent: 5% methanol/chloroform) to obtain the target compound in 92.4% yield (1.89 g).1H-NMR (300 MHz, DMSO) delta 3.48-3.41 (m, 4H), 2.45-2.40 (m, 4H), 2.28-2.22 (m, 5H), 1.81-1.71 (m, 2H), 1.47 (br s, 2H), 1.24 (br s, 24H), 0.85 (t, 3H, J=6.3 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 3h; | 1-(5-Bromo-pyridin-2-yl)-4-methyl-[1,4]diazepane. 2 g of 2,5-dibromopyridine, 3.15 ml of <strong>[4318-37-0]1-methylhomopiperazine</strong> are heated for 3 hours at 110 0C. After addition of ethyl acetate and saturated sodium bicarbonate, the resulting mixture is extracted and the organic phase is dried over sodium sulfate. The residue is purified over silica gel ( ethyl acetate / methanol/ammonium hydroxide [96:2:2]) and yields the title compound as a yellow oil; 1H-NMR (400 MHz, DMSO-d6): 1.85 (p, 2H), 2.42 (t, 2H), 2.54 (t, 2H), 3.53 (t, 2H), 3.66 (t,2H), 6.57 (d, 1 H), , 7.57 (dd, 1H), 8.07 (d, 1H). MS (ESI+) m/z: 272 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In acetonitrile; for 16h;Heating / reflux; | A mixture of 5-fluoro-lambda/-(isopropylcarbamoylmethyl)-2-nitrobenzamide (INTERMEDIATE IV.1 ) (400 mg, 1.4 mmol), <strong>[4318-37-0]1-methylhomopiperazine</strong> (0.20 ml_, 1.6 mmol) and potassium carbonate (1 g) in acetonitrile (20 ml_) were heated at reflux temperature under an Argon atmosphere for 16 h. The mixture was cooled, filtered, the residue washed with DCM (2 X 1 ml_) and the volatiles evaporated under reduced pressure. The red coloured residue was dissolved in DCM (15 ml_), washed with 1 N NaOH (aq.) (2 X 5 mL) and brine (1 X 5 ml_), dried (Na2SCU) and concentrated under reduced pressure to afford N- (isopropylcarbamoylmethyl) -5-(4-methylperhydro- 1, 4-diazepin- 1 -yl) -2-nitrobenzamide (510 mg, 1.4 mmol, 100%) as an orange-red solid. This was used in the next step without further purification.Data for N-(isopropylcarbamoylmethyl)-5-(4-methylperhydro-1,4-diazepin-1-yl)-2- nitrobenzamide: MS (ESI) m/z: 378 ([M+H]+). |
Tags: 4318-37-0 synthesis path| 4318-37-0 SDS| 4318-37-0 COA| 4318-37-0 purity| 4318-37-0 application| 4318-37-0 NMR| 4318-37-0 COA| 4318-37-0 structure
[ 1883347-27-0 ]
2-Methyloctahydro-1H-pyrazino[1,2-a]pyrazine trihydrochloride
Similarity: 0.76
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P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
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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