Introduction：Basic information about 6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone CAS 179688-29-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Basic information
| Product Name: | 6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone |
| Synonyms: | 6,7-BIS(2-METHOXYETHOXY)QUINAZOLIN-4(1H)-ONE;Erlotinib LactaM IMpurity;6,7-Bis(2-Methoxyethoxy)-3H-quinazolin-4-one;6,7-bis-Methoxyethoxy-quinazolin-4-one;Erlotinib iMpurity E;ERLOTINIBINT-F;6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone 6,7-BIS(2-METHOXYETHOXY)QUINAZOLIN-4(1H)-ONE;6,7-bis(2-methoxyethoxy)-1H-quinazolin-4-one |
| CAS: | 179688-29-0 |
| MF: | C14H18N2O5 |
| MW: | 294.3 |
| EINECS: | 605-867-4 |
| Product Categories: | Erlotinib INTERMEDIATES;intermidiate of Erlotinib hydrochloride;Erlotinib;Aromatics;Heterocycles;Intermediates;Aromatics Compounds;Intermediate of erlotinib hydrochloride |
| Mol File: | 179688-29-0.mol |
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6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Chemical Properties
| Melting point | 185-189°C |
| Boiling point | 467.8±55.0 °C(Predicted) |
| density | 1.26±0.1 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | DMSO: ≥10mg/mL |
| form | powder |
| pka | 1.35±0.20(Predicted) |
| color | off-white to light tan |
| InChI | InChI=1S/C14H18N2O5/c1-18-3-5-20-12-7-10-11(15-9-16-14(10)17)8-13(12)21-6-4-19-2/h7-9H,3-6H2,1-2H3,(H,15,16,17) |
| InChIKey | PMQWTUWLIGJTQD-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=C(OCCOC)C(OCCOC)=C2)C(=O)NC=1 |
| CAS DataBase Reference | 179688-29-0(CAS DataBase Reference) |
Safety Information
| WGK Germany | 3 |
| HS Code | 2933.59.8000 |
| Storage Class | 11 - Combustible Solids |
6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Usage And Synthesis
| Chemical Properties | Off-White Solid |
| Uses | An intermediate in the synthesis of Erlotinib (E625000). |
| Biological Activity | CP-380736 is an inhibitor of the epidermal growth factor receptor (EGFR). EGFR is a tyrosine kinase th at activates MAPK, JNK, and Akt pathways, and is an important mediator of several types of cancer, including lung cancer and glioblastoma multiforme. |
| Synthesis | 1208902-93-5 179688-29-0 GENERAL METHODS: To a solution of 6,7-dimethoxyquinazoline (200.0 mg, 1.05 mmol) in anhydrous ethanol (20 mL) was sequentially added 40% peracetic acid (1.0 mL, 5.26 mmol) and concentrated sulfuric acid (0.01 mL, 1.8 mmol). The reaction mixture was stirred in an oil bath at 60 °C for 4-12 h (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the system was cooled to room temperature and residual peroxides were quenched by the addition of excess sodium bisulfite (541.8 mg, 5.26 mmol). After continued stirring for 20 min, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was washed with a solvent mixture of ethanol and petroleum ether (1:1, v/v) to afford 6,7-dimethoxyethoxyquinazolin-4-one (179.7 mg, 83% yield) as a light yellow solid with a melting point of >300°C. The crude product was washed with a solvent mixture of ethanol and petroleum ether (1:1, v/v) to afford 6,7-dimethoxyethoxyquinazolin-4-one as a light yellow solid. |
| References | [1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
[2] Tetrahedron, 2010, vol. 66, # 4, p. 962 - 968 |
6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Preparation Products And Raw materials
| Raw materials | Quinazoline, 6,7-bis(2-methoxyethoxy)--->Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate-->formamide-->Formaldehyde-->Methanol-->Methyl formate-->Formamidine acetate-->METHYL ESTER, 2-AMINO-4,5-BIS(2-METHOXYETHOXY)BENZOIC ACID-->Erlotinib Impurity 20-->Trimethoxymethane |
| Preparation Products | Erlotinib |
