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CAS No. : | 7491-74-9 | MDL No. : | MFCD00079246 |
Formula : | C6H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GMZVRMREEHBGGF-UHFFFAOYSA-N |
M.W : | 142.16 | Pubchem ID : | 4843 |
Synonyms : |
UCB-6215
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.76 |
TPSA : | 63.4 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) : | -8.26 cm/s |
Log Po/w (iLOGP) : | 0.79 |
Log Po/w (XLOGP3) : | -1.54 |
Log Po/w (WLOGP) : | -1.29 |
Log Po/w (MLOGP) : | -0.96 |
Log Po/w (SILICOS-IT) : | -0.21 |
Consensus Log Po/w : | -0.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.38 |
Solubility : | 342.0 mg/ml ; 2.4 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.72 |
Solubility : | 738.0 mg/ml ; 5.19 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.18 |
Solubility : | 93.1 mg/ml ; 0.655 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
In acetonitrile; at 70℃; for 0.0333333h; | Piracetam:Gentisic acid Co-crystal [00211] To <strong>[7491-74-9]piracetam</strong> (16 mg, 0.11 mol) was added gentisic acid (17 mg, 0.11 mol). To the solid mixture was added acetonitrile (1 rnL) and the solution was heated at 70 degrees C for 2 minutes. The homogeneous solution was then cooled to room temperature (22 degrees C) and the solvent was slowly evaporated. After 24 hours at room temperature, a precipitate was observed. The precipitate was collected and dried, which gave a 1:1 <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal as small colorless plates. The crystals were characterized using DSC, melting point (Mel-temp), IR, PXRD, and single crystal x-ray analysis. [00212] DSC analysis of the <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal showed an endothermic transition at about 126 degrees C, as shown in Figure 4. [00213] A MEL-TEMP was used to determine the melting point of the <strong>[7491-74-9]piracetam</strong>: gentisic acid co-crystal. The melting point was determined to be about 124 degrees C. [00214] The <strong>[7491-74-9]piracetam</strong>: gentisic acid co-crystal was characterized by IR spectroscopy. The <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal can be characterized by any one, any two, any three, any four, any five, or any six or more of the peaks in Figure 5 including, but not limited to, 1651, 1596, 1467, 1294, 1221, 1034, 831, 762, and 681 cm'1. [00215] The <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal was also characterized by PXRD. The <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal can be characterized by any one, any two, any three, any four, any five, or any six or more of the peaks in Figure 6 including, but not limited to, 12.70, 14.08, 16.96, 24.79, 27.94, and 32.46 degrees 2-theta. [00216] Single crystal x-ray data (Bruker SMART- APEX CCD) : monoclinic C2/c, a = 27.896(3) angstroms, b = 5.1762(5) angstroms, c = 19.7879(18) angstroms, alpha = 90 degrees, beta = 101.090(2) degrees, gamma = 90 degrees, V = 2803.9(4) cubic angstroms, T = 100(2) K, Z = 8. [00217] Both <strong>[7491-74-9]piracetam</strong> and gentisic acid in their respective free forms are known to be polymorphic. Three polymorphs of <strong>[7491-74-9]piracetam</strong> can be found in the Cambridge Structural Database (CSD). In addition, the Merck Index describes gentisic acid as "dimorphic." The resulting <strong>[7491-74-9]piracetam</strong>:gentisic acid co-crystal from the above preparation may be non-polymorphic. After multiple experiments including dry grinding and wet grinding with several different solvents, only one polymorph of the <strong>[7491-74-9]piracetam</strong>: gentisic acid co-crystal has been observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 70℃; for 0.0833333h; | Piracetam:4-hydroxybenzoic acid Co-crystal [00218] To <strong>[7491-74-9]piracetam</strong> (10 mg, 0.07 mol) was added 4-hydroxybenzoic acid (10 mg, 0.07 mol). To the solid mixture was added acetonitrile (1 mL) and the solution was heated at 70 degrees C for 5 minutes. The homogeneous solution was then cooled to room temperature and the solvent was slowly evaporated. After 24 hours at room temperature (22 degrees C), a precipitate was observed. The precipitate was collected and dried, which gave a 1:1 <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal as small colorless plates. The crystals were characterized using DSC, melting point (Mel-temp), IR, PXRD, and single crystal x-ray analysis. [00219] DSC analysis of the <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal showed an endothermic transition at about 143 degrees C, as shown in Figure 7. [00220] A MEL-TEMP was used to determine the melting point of the <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal. The melting point was determined to be 141 -142 degrees C. [00221] The <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal was characterized by IR spectroscopy. The <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal can be characterized by any one, any two, any three, any four, any five, or any six or more of the peaks in Figure 8 including, but not limited to, 1658, 1596, 1471, 1405, 1265, 1243, 1166, 1125, 945, 923, 857, and 769 cm4. [00222] The <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal was also characterized by PXRD. The <strong>[7491-74-9]piracetam</strong>:4-hydroxybenzoic acid co-crystal can be characterized by any one, any two, any three, any four, any five, or any six or more of the peaks in Figure 9 including, but not limited to, 6.63, 13.48, and 20.42 degrees 2-theta. [00223] Single crystal x-ray data (Bruker SMART-APEX CCD): monoclinic P2(l)/n, a = 14.780(3) angstroms, b = 5.5029(12) angstroms, c = 17.068(4) angstroms, alpha = 90 degrees, beta = 109.557(4) degrees, gamma = 90 degrees, V = 1308.0(5) cubic angstroms, T = 100(2) K, Z = 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol; | EXAMPLE 4 1-Benzhydryl-4-(2-oxo-1-(pyrrolidinyl)methylpiperazine (Compound 19) (I, R1 =benzhydryl, R2 =(2-oxo-1-(pyrrolidinyl)acetyl)methyl) 5.04 g of N-monobenzhydryl-piperazine (0.02 mole) and 2.84 g of 2-oxo-1-pyrrolidinylacetamide (0.02 mole) are dissolved in 100 ml of absolute ethanol, then 2.6 ml of 35% (p.v) formaldehydr solution is added and the reaction mixture subjected to reflux for 12 hours. The reaction mixture is allowed to stand under stirring for 20 hours at room temperature. The ethanol is removed by distillation and the resulting oil is treated with 60 ml of ethyl ether for 1 hour, thus yielding a crystal-like solid which is filtered, washed with ethyl ether and dried under vaccum. 6.9 g crystals of 1-benzhydryl-4-(2-oxo-1(pyrrolidinyl)acetyl)methyl-piperazine (I, R1 =benzhydryl, R2 =(2-oxo-1-(pyrrolidinyl)acetyl)methyl) are obtained. Yield: 85%; m.p. 157 158, 5 C.; IR (KBR), cm-1: 3460, 3220, 1705, 1680, 1545. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In isopropyl alcohol; at 20℃; for 312h; | <strong>[529-44-2]Myricetin</strong> (25 mg, 0.077 mmol) and piracetam (11 mg, 0.077 mmol) were combined in 8 mL isopropyl alcohol with stirring. Resulting solution was filtered and allowed to slowly evaporate at ambient temperature. After 13 days, dark-yellow, block-like crystals (Fig. S1) precipitated (yield 54%). The solid phase was filtered, washed with ethyl acetate, allowed to dry at ambient conditions and used for single-crystal X-ray diffraction. Same procedure was employed to obtain samples for powder diffraction, Raman spectroscopy, thermal analysis (TG-DTA and DSC) and 1H NMR solution study. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | To a stirred solution of docosahexaenoic acid (1.0 eq) in DMF(10.0 v) , DIPEA(3.0 eq) and HATU (1.5 eq) were added at room temperature and stirred for 30.0 minutes, then <strong>[7491-74-9]piracetam</strong> compound- 1 (1.2 eq) was added slowly to it and stirred for 2.0 hrs. Reaction was monitored by TLC. On completion of the reaction, the solvent was removed in vacuo and the crude was diluted with water and extracted twice with DCM. The organic layer was washed with water followed by brine and dried over anhydrous Na2S04 and evaporated under reduced pressure to yield compound - 2 (yield 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 mg | With trifluoroacetic acid; for 3h;Inert atmosphere; Reflux; | General procedure: To a solution of gamma-aminobutyric acid (1.0 mmol, 1 equiv) in 2,2,2-trifluoroethanol (10 mL) were added the aldehyde (1.0 mmol, 1 equiv) and the isocyanide (1.0 mmol, 1 equiv). The mixture was heated at reflux for 3 h, then concentrated and redissolved in trifluoroacetic acid (3 mL). This solution was heated at reflux for 1 h. The reaction mixture was then concentrated in vacuo and the product was isolatedby column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Heating; | General procedure: A suspension of 5 g of 3a-3g in 30 mL of anisole or o-xylene was heated with stirring until it became homogeneous with simultaneous removal of water by distillation.The mixture was allowed to cool down, and the precipitate was filtered off, washed with propan-2-ol, and dried. 2-(2-Oxopyrrolidin-1-yl)acetamide (4a). Solvent anisole. Yield 70-75%, white prisms, mp 152-153C (from i-PrOH); published data: mp 151.5-152.5 [3], 150-153C [11]. 1H NMR spectrum (D2O), delta, ppm: 2.01 quint (2H, CH2, J = 8.0 Hz), 2.39 t (2H, CH2,J = 8.0 Hz), 3.43 t (2H, CH2, J = 8.0 Hz), 3.92 s(2H, CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; In water; at 50℃; for 24h;Sealed tube; | a mixture of 211mg (0.42mmol) UO2(NO3)2·6H2O, 119mg (0.84mmol) <strong>[7491-74-9]piracetam</strong> and 5mL aqueous HNO3 (0.5M) was placed in a glass tube and then heated at 50C for 24h. The resulting yellow liquid phase was left at room temperature in air atmosphere for slow evaporation for one week. 3 was analyzed by scanning electron microscope (Hitachi S-3400N) showing well-shaped multi-facetted bulky crystals of 5-20mum size (Fig. S1c). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; for 0.2h; | General procedure: The DAP-TEO and DAP-PIR cocrystals were obtained bythe solvent-assisted grinding method. Mixtures in 1:1 molarratios of DAP-TEO (400.0 mg of DAT and 660.0 mg of TEO)and DAP-PIR (400.0 mg of DAT and 521.0 mg of PIR) wereground in a mortar with a pestle for 12 min. Before the start ofthe grinding, dichloromethane (0.5 ml) was added and themixture was ground for 3 min. After grinding, the powder wascollected. The cycle of adding dichloromethane (0.5 ml) andgrinding for 3 min was repeated an additional three times until12 min of grinding was completed. The ground powder wascharacterized by IR spectroscopy and powder X-ray diffraction. |
Tags: 7491-74-9 synthesis path| 7491-74-9 SDS| 7491-74-9 COA| 7491-74-9 purity| 7491-74-9 application| 7491-74-9 NMR| 7491-74-9 COA| 7491-74-9 structure
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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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