Acetonitrile → HCID 54759637, compound

HRID 473302Notes

Reaction equation

HRID 473302 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.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].C(#N)C>CN(C)C=O>[S:37]([OH:40])(=[O:39])(=[O:38])[CH3:36].[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 6342AcetonitrileHCID 6395Methanesulfonic Acid2×HCID 46207586Ilorasertib

Product 1

HCID 54759637HCID 54759637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °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 solid (26 mg) was suspended in dimethylformamide (125 μL) at 40° C. with magnetic stirring. Methanesulfonic acid (59 μL, 1 M) was slowly added to A-968660 free base suspension at 40° C. with magnetic stirring. Clear solution obtained after addition of methanesulfonic acid. Acetonitrile (150 μL) was then added to clear solution at 40° C. with magnetic stirring. Amorphous precipitation was observed shortly after the complete addition of the acid solution. The amorphous suspension was heated to 80° C. to obtain a clear solution, and then cooled spontaneously to ambient temperatures. Crystallization was observed upon cooling. Solid was collected by centrifuge filtration.

Workup

  1. customClear solution obtained
  2. customAmorphous precipitation
  3. additionafter the complete addition of the acid solution
  4. customto obtain a clear solution
  5. temperaturecooled spontaneously to ambient temperatures
  6. customCrystallization
  7. temperatureupon cooling
  8. filtrationSolid was collected by centrifuge filtration

Sources & evidence

ORD record
ord-fa3fac23e6ac480384c61b0fed22a80c
Source dataset
uspto-grants-2014_01
Patent number
US08633317B2

Reaction notes

Loading…