Sodium Hydroxide → HCID 178524520, compound

HRID 1778249Notes

Reaction equation

HRID 1778249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([C:30]3[S:34][C:33]([C:35]([O:37]C)=[O:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:22][CH2:23][N:24]([S:27]([C:30]3[S:34][C:33]([C:35]([OH:37])=[O:36])=[CH:32][CH:31]=3)(=[O:28])=[O:29])[CH2:25][CH2:26]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178498325HCID 178498325, compound

Product 1

HCID 178524520HCID 178524520, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a 100-mL round-bottom flask, was placed methyl 5-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)piperidine-1-sulfonyl]thiophene-2-carboxylate (100 mg, 0.15 mmol, 1.00 equip), methanol (20 mL), and 1M sodium hydroxide (20 mL). The resulting solution was stirred overnight at 50° C. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 5-6 with 10% HCl. The solids were collected by filtration. The resulting residue was purified by Prep-HPLC with the following conditions: water with 0.05% TFA and MeOH (60% MeOH up to 85% in 10 min, hold 95% for 1 min, down to 60% in 1 min) to yield 5-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)piperidine-1-sulfonyl]thiophene-2-carboxylic acid; trifluoroacetic acid salt as an off-white solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. filtrationThe solids were collected by filtration
  4. customThe resulting residue was purified by Prep-HPLC with the following conditions
  5. waitwater with 0.05% TFA and MeOH (60% MeOH up to 85% in 10 min
  6. customfor 1 min

Sources & evidence

ORD record
ord-4e839d8a47124414b58d9b8fa3e442ae
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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