Dasatinib butanolate → Dasatinib

HRID 1008943Notes

Reaction equation

HRID 1008943 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1.C([O-])CCC>C(O)C.O>[CH3:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[S:15][C:14]([NH:16][C:17]3[CH:18]=[C:19]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]4)[N:20]=[C:21]([CH3:23])[N:22]=3)=[N:13][CH:12]=2)=[O:10])=[C:6]([Cl:33])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86630108Dasatinib butanolate

Product 1

HCID 3062316Dasatinib

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Dasatinib butanolate (form BU-2, 1.00 g, 2.05 mmol) was heated in a mixture of ethanol (22 ml) and water (3 ml) at 75-80° C. to achieve complete dissolution. Water was added (8 ml) at the same temperature. The solution was cooled to 70° C. and maintained at 70° C. for 1 h. Temperature was lowered from 70° C. to 5° C. during 2 h, and maintained between 0-5° C. for 2 h. The product was filtered and washed with EtOH/H2O (1:1, 2×10 ml) and dried under reduced pressure at 40° C./8 h. Yield: 0.61 g.

Workup

  1. dissolutiondissolution
  2. temperaturemaintained at 70° C. for 1 h
  3. temperaturemaintained between 0-5° C. for 2 h
  4. filtrationThe product was filtered
  5. washwashed with EtOH/H2O (1:1, 2×10 ml)
  6. customdried under reduced pressure at 40° C./8 h

Sources & evidence

ORD record
ord-ae16668c24ff4b9aac1fde684f866ca4
Source dataset
uspto-grants-2011_07
Patent number
US07973045B2

Reaction notes

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