Phosphate → Tirbanibulin

HRID 1398008Notes

Reaction equation

HRID 1398008 reaction equation
P([O-])([O-])([O-])=O.S(O)(=O)(=O)C.[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])=[N:30][CH:31]=3)=[CH:22][CH:21]=2)[CH2:13][CH2:12]1>O>[CH:40]1[CH:39]=[CH:38][C:37]([CH2:36][NH:35][C:33]([CH2:32][C:29]2[CH:28]=[CH:27][C:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][CH2:18][CH2:17][N:14]4[CH2:15][CH2:16][O:11][CH2:12][CH2:13]4)=[CH:25][CH:24]=3)=[CH:31][N:30]=2)=[O:34])=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 1061PhosphateHCID 25100013Tirbanibulin Mesylate2×

Product 1

HCID 23635314Tirbanibulin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solubility experiments were also performed using pH 2.0 phosphate buffer and DI water pH 6.9 and KX2-391•MSA, Form A. Each vial was filled with approximately 50 mg of KX2-391•MSA, Form A and 100 μL aliquots of the corresponding solvent was added until complete dissolution was observed, followed by stirring at room temperature for one and five days. The solids obtained were isolated by filtration, dried under vacuum at room temperature and analyzed by HPLC. The initial HPLC purity of KX2-391•MSA, Form A was 99.4 (% area). The solubility by HPLC of KX2-391•MSA, Form A in phosphate buffer/RT was >500 mg/mL and HPLC purity was measured to be 99.4. The solubility by HPLC of KX2-391•MSA, Form A in DI H2O/RT was >500 mg/mL and HPLC purity was measured to be 99.4.

Workup

  1. additionwas added until complete dissolution
  2. customThe solids obtained
  3. customwere isolated by filtration
  4. customdried under vacuum at room temperature
  5. customRT
  6. customin DI H2O/RT

Sources & evidence

ORD record
ord-5867962570a84d17867a8f965cc69850
Source dataset
uspto-grants-2014_12
Patent number
US08901297B2

Reaction notes

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