Structure of L-Prolinamide
CAS No.: 7531-52-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 7531-52-4 |
| Formula : | C5H10N2O |
| M.W : | 114.15 |
| SMILES Code : | O=C(N)[C@H]1NCCC1 |
| MDL No. : | MFCD00005253 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 8 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.8 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 2.0 |
| Molar Refractivity | 33.66 |
| TPSA ? Topological Polar Surface Area: Calculated from |
55.12 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.73 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.87 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.16 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.78 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.02 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.42 |
| Log S (ESOL):? ESOL: Topological method implemented from |
0.07 |
| Solubility | 133.0 mg/ml ; 1.17 mol/l |
| Class? Solubility class: Log S scale |
Highly soluble |
| Log S (Ali)? Ali: Topological method implemented from |
0.19 |
| Solubility | 178.0 mg/ml ; 1.56 mol/l |
| Class? Solubility class: Log S scale |
Highly soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.34 |
| Solubility | 51.8 mg/ml ; 0.454 mol/l |
| Class? Solubility class: Log S scale |
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 |
No |
| 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) |
No |
| 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 |
-7.61 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 |
1.0 |
| 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 |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.47 |
* 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 |
|---|---|---|
| With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; | Example 6 (S)-pyrrolidine-1 ,2-dicarboxylic acid 2-amide 1-[(2-tert-butyl-4'-methyl- [4,5']bithiazolyl-2'-yl)-amide]; A mixture of imidazole-1-carboxylic acid (2-tert-butyl-4'-methyl-[4,5']bithiazolyl-2'-yl)-amide (40 mg), L-proline amide (20 mg) and triethylamine (0.02 ml) in DMF (1 ml) is allowed to stand at room temperature for 18 hours. Following evaporation of the reaction mixture purification by crystallisation from aqueous methanol gives the title compound as a white solid. Hplc/MS (Method B) RT 2.40 minutes, M+H 394.1 and M-H 392.3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95.3% | With hydrogenchloride; In water; at 103℃; for 2h; | 44.41 g of 1-acetyl-2-pyrrolidinecarboxamide was added to 160 mL of 2N HCl.Raise the temperature to 103 C reflux reaction,During the reaction, the temperature of the system is kept at the micro-reflow state.Co-reacted for 2 hours,After completion of the reaction, the mixture was concentrated to a small volume until crystallization, pH was adjusted to 8, filtered, and dried to give the desired product, L-prolinamide, 31.05 g, yield 95.3%. Detection of D-type isomerismThe purity of the solution was 0.11%, and the purity was determined by high performance liquid chromatography HPLC to be 99.1%. |