Structure of 93102-05-7
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 93102-05-7 |
Formula : | C13H23NOSi |
M.W : | 237.41 |
SMILES Code : | C[Si](CN(COC)CC1=CC=CC=C1)(C)C |
MDL No. : | MFCD00674005 |
Boiling Point : | No data available |
InChI Key : | RPZAAFUKDPKTKP-UHFFFAOYSA-N |
Pubchem ID : | 353442 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H341-H227 |
Precautionary Statements: | P501-P202-P210-P201-P264-P280-P302+P352-P370+P378-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235-P405 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.54 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 72.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.47 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.82 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.81 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.42 |
Solubility | 0.0895 mg/ml ; 0.000377 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.49 |
Solubility | 0.0774 mg/ml ; 0.000326 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.35 |
Solubility | 0.0107 mg/ml ; 0.0000449 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.23 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.51 |
* 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 |
---|---|---|
96% | With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 17h; | A solution of B1_3 (22.06 g,92.7 mmol) and methyl acrylate (C2, 11.54 g, 139.0 mmol) inDCM(100 mL) was cooled to 0 C.Asolutionof trifluoroacetic acid (12.71 g, 111.2 mmol) in DCM (50 mL) was added slowly by drop to the reactionmixture. The solution was warmed to room temperature and stirred for 17 h. NaHCO 3 saturatedsolution (150 mL) was added to the solution and stirred until no gas was produced. The mixture waspartitioned between water and DCM. The organic phase was washed with brine, dried over Na2SO4and concentrated to give the title compound (19.53 g, 96%). 1H-NMR (CDCl3) 7.35-7.23 (m, 5H),3.69 (s, 3H), 3.64 (s, 2H), 3.12-2.99 (m, 1H), 2.98-2.87 (m, 1H), 2.79-2.69 (m, 1H), 2.69-2.57 (m, 1H),2.58±2.48 (m, 1H), 2.17±2.04 (m, 2H). MS (ESI, pos, ion): 219.9 [M+ H]+. |
96.8% | With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; | A solution of 3 (23.5g, 98.98mmol) and methyl acrylate (12.8g, 148.48mmol) in DCM (100 mL) was treated with TFA (13.5 g, 118.78 mmol) in DCM (50 mL) at 0C. The mixture was stirred at 0C for 0.5h, overnight at room temperature. The saturated aqueous NaHCO3 solution was added in the mixture, and it was stirred for 2h. The organic phase was washed with brine, dried with anhydrous Na2SO4, and concentrated in vacuo to give the compound 4 (21.01g, 96.8%). |
1420 g | With trifluoroacetic acid; In dichloromethane; at 0 - 20℃;Large scale; | To a 250 mL multi-vial was added 1530.0 g (6.5 mol) of benzylmethoxymethyltrimethylsilylmethylamine,31.80 g (3.7 mol)Methyl acrylate and 38 mL of dichloromethane,A solution of 44.0 g (0.4 mol) of trifluoroacetic acid at a mass concentration of 10% was slowly added dropwise at 0 C,After completion of the dropwise addition, the mixture was stirred at room temperature overnight, and the mixture was concentrated under reduced pressure,The residueRespectively, washed with saturated sodium bicarbonate solution and saturated sodium chloride solution,Combined organic phase,The organic phase passes through anhydrous sulfuric acidSodium drying, filtration,The filtrate was concentrated under reduced pressure,To obtain 1420.0 g of crude 1-benzylpyrrolidine-3-carboxylate as a crude product 100%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | To a solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (92.65 g, 444.1 mmol) in dichloromethane (425 mL) was added trifluoroacetic acid (3.4, 44.4 mmol). The reaction mixture was cooled with a water bath and a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (164.7 g, 666.1 mmol) in dichloromethane (325 mL) was added dropwise over a period of 1.5 h. It was stirred for 22 h at ambient temperature. Further N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (27.5 g, 111.0 mmol) in dichloromethane (50 mL) was added and stirring was continued for 2 h at ambient temperature. The solvent was distilled off and the residue was taken up in dioxane (950 mL). After addition of water (475 mL) and sodium hydroxide (32%, 114.3 mL, 1.23 mol), it was stirred for 67 h at ambient temperature. After concentration the residue was diluted with water (400 mL) and extracted with tert-butylmethylether (400 mL). The organic layers were washed with water (400 mL). The aqueous layers were combined, cooled to 5 C. and set to pH=1.5 with aqueous HCl (25%, 172). After stirring for 1 h at 5 C., the solid was filtered off and was washed with water (1400 mL) and ethanol (400 mL). Drying (50 C., 25 mbar) afforded the title compound (109.85 g, 79%) as an off-white solid. MS m/e: 312.2/314.1 [M-H]-. | |
79% | b) l-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-lH-pyrrole-3-carboxylic acidTo a solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (92.65 g, 444.1 mmol) in dichloromethane (425 mL) was added trifluoro acetic acid (3.4, 44.4 mmol). The reaction mixture was cooled with a water bath and a solution of N-(methoxymethyl)-N- (trimethylsilylmethyl)benzylamine (164.7 g, 666.1 mmol) in dichloromethane (325 mL) was added dropwise over a period of 1.5 h. It was stirred for 22 h at ambient temperature. Further N- (methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (27.5 g, 111.0 mmol) indichloromethane (50 mL) was added and stirring was continued for 2 h at ambient temperature. The solvent was distilled off and the residue was taken up in dioxane (950 mL). After addition of water (475 mL) and sodium hydroxide (32%, 114.3 mL, 1.23 mol), it was stirred for 67 h at ambient temperature. After concentration the residue was dilluted with water (400 mL) and extracted with tert-butylmethylether (400 mL). The organic layers were washed with water (400 mL). The aqueous layers were combined, cooled to 5 C and set to pH=1.5 with aqueous HC1 (25 %, 172). After stirring for 1 h at 5 C, the solid was filtered off and was washed with water (1400 mL) and ethanol (400 mL). Drying (50 C, 25 mbar) afforded the title compound (109.85 g, 79%) as an off-white solid. MS m/e: 312.2/314.1 [M-H] | |
60% | b) 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (IIa) At r.t., a solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methyl amine (116.8 g, 0.49 mol) in CH2Cl2 (260 ml) was added dropwise over 90 min to a stirred solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (72.0 g, 0.34 mol) and trifluoroacetic acid (2.5 ml, 0.03 mol) in CH2Cl2 (350 ml). The reaction mixture was stirred at 25 C. overnight and afterwards evaporated to dryness. The residue was dissolved in dioxane (0.8 l); an aqueous solution of NaOH (91.0 ml, 1.02 mol, 3 eq.) was added, and the resulting emulsion was stirred at r.t. for 48 h. The low boiling organic solvent was removed under vacuum, water (0.9 l) was added, and the aqueous layer was separated and washed with TBME (1 l). The aqueous layer was then acidified to a pH value of 2.5 by addition of 25% HCl. The resulting suspension was stirred overnight; the white precipitate was filtered off, washed with water and ethanol and dried under high vacuum to yield 62.0 g (60%) of IIa as a white solid. ES-MS m/e: 312.4 (M-H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 2.0h; | Step 2; To a stirred solution of <strong>[3883-39-4]5-methyl-2-vinylpyridine</strong> (600 mg, 1.87 mmol) in dry CH2CI2 (6 mL) was added N-benzyl-1-methoxy-N- ((trimethylsilyl)methyl)methanamine (1.42 g, 6.0 mmol) and TFA (570 mg, 5.0 mmol) at 00C. The mixture was stirred at rt for 2 TLC showed the disappearance of starting material. The mixture was quenched with satd aq NaHCO3 (15 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column on silica cartridge eluted with PE/EA=5:1 to afford 2-(1-benzyl-pyrrolidin-3-yl)-5-methyl-pyridine (450 mg, 35%) as a yellow oil |
Tags: 93102-05-7 synthesis path| 93102-05-7 SDS| 93102-05-7 COA| 93102-05-7 purity| 93102-05-7 application| 93102-05-7 NMR| 93102-05-7 COA| 93102-05-7 structure
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