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| | 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Basic information |
| | 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Chemical Properties |
| Melting point | 104.0 to 108.0 °C | | Boiling point | 576.2±50.0 °C(Predicted) | | density | 1.261±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 5.37±0.11(Predicted) | | color | Off-White to Pale Beige | | InChI | InChI=1S/C18H22N4O3/c1-3-25-17(23)9-11-22(16-6-4-5-10-21-16)18(24)13-7-8-15(20-2)14(19)12-13/h4-8,10,12,20H,3,9,11,19H2,1-2H3 | | InChIKey | PCPATNZTKBOKOY-UHFFFAOYSA-N | | SMILES | N(C1N=CC=CC=1)(CCC(=O)OCC)C(C1C=CC(NC)=C(N)C=1)=O | | LogP | 1.37 at 20℃ |
| | 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Usage And Synthesis |
| Uses | Alzheimer's disease therapeutic, Co Q10 analog, antioxidant | | Uses | Ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate is the impurity of Dabigatran (D100090), which is a nonpeptide, direct thrombin inhibitor and is antithrombotic. | | Synthesis | (D) Preparation of Intermediate VI: In a hydrogenation reactor, 43 g of ethyl 3-(4-(methylamino)-3-nitro-N-(pyridin-2-yl)benzoylamino)propionate and 4.7 g of nickel Nguyenne catalyst were added. 4 mL of tetrahydrofuran was added as solvent and three nitrogen substitutions were performed to remove air. The reaction mixture was then stirred under hydrogen atmosphere and heated to 60°C. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, a filtration operation was carried out and the filter cake was washed with a small amount of tetrahydrofuran. The filter cake was recovered and disposed properly. The filtrate was dried over anhydrous sodium sulfate, diafiltrated again and finally concentrated to dryness under reduced pressure to give 38.3 g of intermediate VI (6) in 96% yield. | | References | [1] Patent: CN104031031, 2017, B. Location in patent: Paragraph 0028; 0033; 0035; 0040; 0042; 0047
[2] Patent: WO2007/71742, 2007, A1. Location in patent: Page/Page column 22-23
[3] Patent: WO2007/71743, 2007, A1. Location in patent: Page/Page column 18
[4] Patent: CN105461688, 2016, A. Location in patent: Paragraph 0043; 0044
[5] Patent: WO2007/71742, 2007, A1. Location in patent: Page/Page column 22 |
| | 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Preparation Products And Raw materials |
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