Acetic Acid → HCID 86688195, compound

HRID 1428300Notes

Reaction equation

HRID 1428300 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[C:40]([OH:43])(=[O:42])[CH3:41]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:38])([F:39])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[C:40]([O-:43])(=[O:42])[CH3:41]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 644241Nilotinib

Product 1

HCID 86688195HCID 86688195, compound

Conditions

Temperature
40 °C

Procedure

Nilotinib base (3.00 g, 5.66 mmol) was suspended in glacial acetic acid (12 mL, 4V) and the resulting mixture was heated to 40° C. with stirring, leading to dissolution. Stirring was continued for another 5 h at the same temperature leading to gradual precipitation. The mixture was then cooled to −18° C. and maintained at this temperature over a period of 15 h, leading to the formation of a large solid block. The solid was allowed to warm to room temperature and then heated to 40° C. for 4 h leading to a viscous suspension. The suspension was filtered and the collected solid was dried in a vacuum oven (35 mmHg) at 40° C. for 24 h to give Nilotinib acetate form VI (1.57 g) as a yellow solid.

Workup

  1. dissolutionleading to dissolution
  2. stirringStirring
  3. customleading to gradual precipitation
  4. temperatureThe mixture was then cooled to −18° C.
  5. temperaturemaintained at this temperature over a period of 15 h
  6. temperatureto warm to room temperature
  7. temperatureheated to 40° C. for 4 h
  8. filtrationThe suspension was filtered
  9. customthe collected solid was dried in a vacuum oven (35 mmHg) at 40° C. for 24 h

Sources & evidence

ORD record
ord-faab99d488554dd585d5ad352a29c610
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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