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Chemical Structure| 936901-75-6 Chemical Structure| 936901-75-6

Structure of 936901-75-6

Chemical Structure| 936901-75-6

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Product Details of [ 936901-75-6 ]

CAS No. :936901-75-6
Formula : C11H13BrN4O
M.W : 297.15
SMILES Code : O[C@@]1(C)C[C@@H](C2=NC(Br)=C3C(N)=NC=CN32)C1
MDL No. :MFCD26793847

Safety of [ 936901-75-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 936901-75-6 ]

* 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.

  • Downstream synthetic route of [ 936901-75-6 ]

[ 936901-75-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 867164-54-3 ]
  • [ 936901-75-6 ]
  • [ 867160-71-2 ]
YieldReaction ConditionsOperation in experiment
65% EXAMPLESExample 1 : c/s-3-[8-amino-1-(2-phenyl-quinolin-7-yl)-imidazo[1 ,5-a]pyrazin-3-yl]-1- methylcyclobutanol (OSI-906) (Compound 1 ):A vessel was charged with DMF (79 kg), c/s-3-(8-amino-1-bromo-imidazo[1 ,5-a]pyrazin- 3-yl)-1 -methylcyclobutanol (16.725 kg), 2-phenyl-7-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2- yl)-quinoline (22.4 kg), triphenylphosphine (0.586 kg), cesium carbonate (36.7 kg) and water (20.1 kg). The reaction mixture was degassed and heated to 95-105 C and a solution of palladium acetate (0.125 kg) in DMF (9.8 kg) was added and rinsed in with DMF (5.9 kg). After the reaction was complete, water (154 kg) was added keeping the temperature above 70 C. The resultant slurry was cooled and the solid was collected by filtration. After washing with a mixture of DMF (9.4 kg) and water (23.4 kg) and then water (67 kg) the solid was suspended in water (167 kg) at 50 C and the pH of the mixture was adjusted to 2.9 with 6N hydrochloric acid (10.9 kg). The resultant yellow slurry was filtered to remove the major impurities and the cake was washed with water (67 kg). The acid solution was stirred at 50-55 C and polymer bound trimercaptotriazine resin (MP-TMT) (4.9 kg) was added. The mixture was stirred for 23 hours, the resin was removed by filtration and the cake was washed with water (58 kg).The resultant acid solution was diluted with 2-propanol (82 kg), the temperature was adjusted to 35-45 C and the pH was adjusted to 5.0 by the addition of 1 N sodium hydroxide solution. The mixture was cooled, the yellow product was collected by filtration and was washed with water (33 kg). The solid was re-suspended in water (157 kg) stirred, filtered and washed with water (125 kg). The solid was dried under vacuum at 45-55 C (the resulting material was a hemihydrate of OSI-906 designated Form C) and was then stirred in refluxing 2- propanol (157 kg) for 3 hours. The mixture was cooled and the solid was isolated by filtration. After washing with 2-propanol (26.7 kg), the product was dried at 45-55 C under vacuum to yield 15.6 kg (65% yield) of OSI-906. The resulting material was an anhydrous crystalline form of OSI-906 designated Form A
 

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