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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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. : | 2835-68-9 |
Formula : | C7H8N2O |
M.W : | 136.15 |
SMILES Code : | O=C(N)C1=CC=C(N)C=C1 |
MDL No. : | MFCD00007999 |
InChI Key : | QIKYZXDTTPVVAC-UHFFFAOYSA-N |
Pubchem ID : | 76079 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
70% | Hydrochloric acid (35%) (3.2 L) was added to a cooled solution of 4-aminobenzamide (2.0 Kg, 14.69 mol) in water (14 L, 7 volumes) at 5-100C. Then p-toluene sulphonic acid (10.1 Kg, 3.44 mol) was added to the reaction mixture and further cooled to -5C to -100C. Sodium nitrite (1.76 Kg, 25.7 mol) was dissolved into water (4 L, 2 volumes) and added to the cooled reaction mixture over a period of 2.5 hours at -5C to -100C and further stirred for 4 hours. Sodium sulphite (5.6 Kg, 44.4 mol) was dissolved into water (16 L, 8 volumes) and added dropwise to the diazonium salt over a period of 3 hours at a temperature of -5C to -100C. After stirring for 2 hours, the temperature of the reaction mixture was allowed to rise to ambient and stirred for 12 hours. The reaction was monitored by TLC. Methanol (16 L, 8 volumes) was added to the yellow suspension and 4-phthalimido- cyclohexanone (4.64 Kg, 19.07 mol) was added portionwise at a temperature of 40-450C. After maintaining the reaction mixture at 40-450C for 30 minutes, the temperature of the reaction mixture was raised to 70-750C and maintained for 8 hours. After completion of the reaction, the mixture was cooled to 25-300C, filtered and washed with water (40 L). The wet cake was mixed with water (40 L) and the pH adjusted to 7-8 using 10% potassium carbonate (aq) solution, and the slurry was filtered and washed with water (40 L). The product was dried under vacuum at 60-650C. The crude product was purified by reflux in dichloromethane (30 L) and dried to afford the title compound (3.70 Kg). Molar yield: 70%HPLC purity: 98.06% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added 4-Aminobenzamide (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-carbamoylphenyl)amino)-lH-pyrazole-4-carboxamide as a a yellow powder. Product was allowed to dry under vacuum for 1 hr. 5-amino-3-((4-carbamoylphenyl)amino)-lH-pyrazole-4-carboxamide |