Dasatinib i-propanolate → Dasatinib

HRID 562605Notes

Reaction equation

HRID 562605 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-])(C)C>C(O)(C)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

3

Reactant 1

HCID 86630109Dasatinib i-propanolate

Product 1

HCID 3062316Dasatinib

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

Dasatinib (form A3, 3.50 g) was dissolved in a mixture of i-PrOH—H2O 30:8 (in 140 ml) under reflux. The solution was slowly cooled to about 70° C. The product started to crystallized at 65-70° C. Temperature was kept at this value for about 20 min then it was decreased to 50° C. and kept for 15 min. The mixture was slowly cooled to room temperature and stirred at room temperature for 1 h. The product was filtered off, washed with i-PrOH (2×) and dried under reduced pressure at 50° C. for 3 h. Yield: 2.44 g.

Workup

  1. temperatureunder reflux
  2. customto crystallized at 65-70° C
  3. customwas decreased to 50° C.
  4. waitkept for 15 min
  5. temperatureThe mixture was slowly cooled to room temperature
  6. filtrationThe product was filtered off
  7. washwashed with i-PrOH (2×)
  8. customdried under reduced pressure at 50° C. for 3 h

Sources & evidence

ORD record
ord-8d03422b14b2435392595a8fb1541143
Source dataset
uspto-grants-2011_11
Patent number
US08067423B2

Reaction notes

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