Sodium Hydroxide → Cimlanod

HRID 1749192Notes

Reaction equation

HRID 1749192 reaction equation
C[C@H]1[O:7][C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCCCCS([O-])(=O)=O)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.[Na+].[OH-].[Na+].[OH:88][NH:89][S:90]([C:93]1C=[CH:97][CH:96]=[C:95](S(C)(=O)=O)[CH:94]=1)(=[O:92])=[O:91]>O>[OH:88][NH:89][S:90]([C:93]1[O:7][C:96]([CH3:97])=[CH:95][CH:94]=1)(=[O:92])=[O:91]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76901580N-Hydroxy-3-methanesulfonylbenzene-1-sulfonamide2×HCID 91886200Sulfobutylether--Cyclodextrin

Product 1

HCID 76685198Cimlanod

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Additionally, a sample of the compound of formula (1) was prepared in water to determine the approximate solubility of the compound in the absence of excipients (e.g., CAPTISOL®). A concentration of approximately 300 mg/mL was achieved, not accounting for the volume contribution of the compound. The pH of the sample was determined to be 2.8, which was adjusted to the target of 4.0 using 0.1 N NaOH. Upon pH adjustment, precipitation of a small amount of solid was observed. The clear solution was diluted in acetonitrile and analyzed by HPLC, resulting in an observed solution concentration of 268 mg/mL. A similar analysis was performed for the compound of formula (2). The compound of formula (2) has a solubility of approximately 10 mg/mL.

Workup

  1. customUpon pH adjustment, precipitation of a small amount of solid
  2. additionThe clear solution was diluted in acetonitrile
  3. customresulting in an observed solution concentration of 268 mg/mL

Sources & evidence

ORD record
ord-22b42041d4d4440999f071e4d419c272
Source dataset
uspto-grants-2015_10
Patent number
US09156804B2

Reaction notes

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