Lithium Hydroxide → HCID 136364259, compound

HRID 1700299Notes

Reaction equation

HRID 1700299 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:28]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:29])[CH2:15][CH:16]=[CH:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([C:25](=[NH:27])[NH2:26])[CH:19]=3)=[CH:10][C:9]=2[C:37]([F:40])([F:39])[F:38])[CH2:3][CH2:2]1.[Li+].[OH-].FC(F)(F)C(O)=O>C(O)C.O>[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:28]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[CH2:15][CH:16]=[CH:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([C:25](=[NH:26])[NH2:27])[CH:19]=3)=[CH:10][C:9]=2[C:37]([F:38])([F:39])[F:40])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 137182989HCID 137182989, compound

Product 1

HCID 136364259HCID 136364259, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To 4-(piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(ethoxycarbonyl)ethylcarbonyl)-N-(3-(6-(hydroxy)-3-amidinophenyl)prop-2-en-1-yl)benzenamine (2.0 g) in 100 mL ethanol/H2O (50/50) was added LiOH (0.56 g) at ambient temperature and the resulting solution was stirred at ambient temperature for 4 hours. The reaction was acidified with trifluoroacetic acid, concentrated, separated on HPLC (CH3CN/H2O, gradient) and freeze-dried to afford 4-(piperdin-4-yl)oxy-3-trifluoromethyl-N-(2-(carboxy)ethylcarbonyl)-N-(3-(6-(hydroxy)-3-amidinophenyl)prop-2-en-1-yl)benzenamine.

Workup

  1. concentrationconcentrated
  2. customseparated on HPLC (CH3CN/H2O, gradient)
  3. customfreeze-dried

Sources & evidence

ORD record
ord-40d2d3d1622d4dbeb5437bec8ddeb075
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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