Sodium Hydroxide → HCID 118324110, compound

HRID 1778312Notes

Reaction equation

HRID 1778312 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([NH:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=O)[CH:18]=2)[NH:15][C:14](=[O:28])[CH:13]=[C:12]3[NH:29][CH:30]2[CH2:35][CH2:34][N:33]([S:36]([C:39]([F:42])([F:41])[F:40])(=[O:38])=[O:37])[CH2:32][CH2:31]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:49][C:46]1[CH:45]=[CH:44][C:43]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([N:19]4[CH2:20][CH2:21][CH2:22][C:23]4=[O:25])[CH:18]=2)[NH:15][C:14](=[O:28])[CH:13]=[C:12]3[NH:29][CH:30]2[CH2:35][CH2:34][N:33]([S:36]([C:39]([F:41])([F:42])[F:40])(=[O:38])=[O:37])[CH2:32][CH2:31]2)=[CH:48][CH:47]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118324039HCID 118324039, compound

Product 1

HCID 118324110HCID 118324110, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-((6-(bis(4-chlorophenyl)methyl)-2-oxo-4-((1-((trifluoromethyl)sulfonyl)piperidin-4-yl)amino)-1,2-dihydroquinolin-8-yl)amino)butanoate (20 mg, 0.027 mmol) in THF (1 mL) was added 1N NaOH solution (0.12 mL) and mixture was stirred at room temperature for 3.5 hr. No more starting material was observed. The reaction was concentrated and neutralized to pH=5 with 1N HCl aqueous solution. The solid was extracted with EtOAc three times. The organics were concentrated and purified by chromatography (silica gel column, 100% EtOAc to yield 6-(bis(4-chlorophenyl)methyl)-8-(2-oxopyrrolidin-1-yl)-4-((1-((trifluoromethyl)sulfonyl)piperidin-4-yl)amino)quinolin-2(1H)-one.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionThe solid was extracted with EtOAc three times
  3. concentrationThe organics were concentrated
  4. custompurified by chromatography (silica gel column, 100% EtOAc

Sources & evidence

ORD record
ord-0c7d3a468a124a788871b85fa379f68f
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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