| Identification | Back Directory | [Name]
Temozolomideacid | [CAS]
113942-30-6 | [Synonyms]
TMZA
104425
Temozolomideacid
teMozoloMide acid 97%
Temozolomide Impurity 1
Temozolomide Impurity C
Temozolamide Impurity A
TEMOZOLOMIDE ACID; TMZA
Temozolomide EP Impurity B
Temozolomide Impurity 2(EP-B)
Temozolomide-8-carboxylic acid
Temozolomide EP Impurity B (Temozolomide Acid)
Temozolomide Impurity 2（Temozolomide EP Impurity B）
3-Methyl-4-oxo-8-imidazolo[5,1-d][1,2,3,5]tetrazinecarboxylic acid
3-Methyl-4-oxo-3,4-dihydroiMidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid
3,4-Dihydro-3-Methyl-4-oxo-iMidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic Acid
Imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo- | [Molecular Formula]
C6H5N5O3 | [MDL Number]
MFCD12032160 | [MOL File]
113942-30-6.mol | [Molecular Weight]
195.137 |
| Chemical Properties | Back Directory | [Melting point ]
166-168°C | [Boiling point ]
487.7±37.0 °C(Predicted) | [density ]
1.97±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
2.88±0.20(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A metabolite of Temozolomide (T017775) as antitumor agent. | [Synthesis]
General procedure: Example 1 Preparation of 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (EP0252682)
1. 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (2.577 mmol, 0.5 g) was mixed with concentrated sulfuric acid (4 mL) under stirring conditions.
2. a solution was prepared by dissolving sodium nitrite (9.4 mmol, 0.65 g) in 2.6 mL of water.
3. Slowly add the aqueous sodium nitrite solution dropwise to the above mixture under cooling in an ice bath (keeping the temperature below 15°C).
4. After the dropwise addition, the reaction mixture was stirred at room temperature overnight.
5. 10 g of ice was added to the reaction mixture and cooling was continued in an ice bath for 1 hour.
6. The solid product was collected by filtration.
7. The collected solid product was dried under vacuum to give 0.493 g of 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid.
The yield was 98.6%. | [References]
[1] European Journal of Medicinal Chemistry, 2002, vol. 37, # 4, p. 323 - 332
[2] Patent: EP1798234, 2007, A1. Location in patent: Page/Page column 11
[3] Patent: US2018/79754, 2018, A1. Location in patent: Paragraph 0082; 0101-0102
[4] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 691 - 702
[5] Journal of Medicinal Chemistry, 2002, vol. 45, # 25, p. 5458 - 5470 |
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