Acetone → HCID 54767922, compound

HRID 1429859Notes

Reaction equation

HRID 1429859 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH2:34][OH:35])[CH:32]=2)=[CH:4][N:3]=1.CC(C)=O.[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43]>O>[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43].[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:15][CH:16]=3)=[CH:9][S:10][C:6]=2[C:5]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH2:34][OH:35])[CH:32]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 311Citric AcidHCID 46207586Ilorasertib

Product 1

HCID 54767922HCID 54767922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea free base solids (399.87 mg) was added to 20 mL of acetone:water mixture (75:25 v:v) and heated with stirring at 70° C. for 30 minutes. The sample remained as a suspension. Citric acid (1.2 mL, 1 M) solution in water was added with continued stirring at 70° C. At the end of approximately one hour, the sample was almost completely dissolved. The sample was allowed to cool slowly to ambient temperatures overnight. The suspension was filtered through a 0.22 micron PTFE syringe filter. The filtrate was evaporative cooled by applying vacuum. Amorphous material precipitated forming a milky suspension, which turned into a “gummy” material (sticky mass) after several minutes. The sample was sonicated for approximately thirty minutes, upon which crystallization occurred. The crystalline solid was collected by vacuum filtration.

Workup

  1. stirringwith continued stirring at 70° C
  2. dissolutionAt the end of approximately one hour, the sample was almost completely dissolved
  3. temperatureto cool slowly to ambient temperatures overnight
  4. filtrationThe suspension was filtered through a 0.22 micron PTFE syringe
  5. filtrationfilter
  6. temperatureThe filtrate was evaporative cooled
  7. customAmorphous material precipitated
  8. customforming a milky suspension, which
  9. waitturned into a “gummy” material (sticky mass) after several minutes
  10. customThe sample was sonicated for approximately thirty minutes, upon which crystallization
  11. filtrationThe crystalline solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-afb7e201b3eb41ee850ff09ea77b436d
Source dataset
uspto-grants-2015_01
Patent number
US08940759B2

Reaction notes

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