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p-Toluenesulfonic acid monohydrate → HCID 86732643, compound

HRID 517287
Notes
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Reaction equation

HRID 517287 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[O:12][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([NH:28][OH:29])=[O:27])=[CH:24][CH:25]=1)=[O:15])[CH3:3].C(O)(C)C.O.O.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>O>[CH3:3][N:2]([CH2:4][C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[O:12][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([NH:28][OH:29])=[O:27])=[CH:24][CH:25]=1)=[O:15])[CH3:1].[S:42]([C:39]1[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=1)([O-:45])(=[O:44])=[O:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11749858AbexinostatHCID 21889133Propan-2-ol--water (1/1)

Product 1

HCID 86732643HCID 86732643, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

1.66 kg of abexinostat (free base) are placed in 9.48 kg of a mixture of isopropanol/water (50/50 weight/weight) at ambient temperature. para-Toluenesulphonic acid monohydrate (0.83 kg) in 2.36 kg of water is added at ambient temperature. The mixture is then heated at 75° C. for 30 minutes before being cooled to 0° C. When crystallisation is complete, the suspension is filtered at 20° C. After drying, crystalline form I of abexinostat tosylate is obtained in a yield of about 85% and with a purity greater than 99%. The solid was characterised by the X-ray powder diffraction diagram, Raman spectrum and NMR spectrum as set out in Examples 3-5 and 6 hereinbelow.

Workup

  1. temperaturebefore being cooled to 0° C
  2. customWhen crystallisation
  3. filtrationthe suspension is filtered at 20° C
  4. customAfter drying

Sources & evidence

ORD record
ord-28d80f4d165e4e118b7199aa8aacfbd0
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes