Lithium Hydroxide → HCID 136364262, compound

HRID 1700302Notes

Reaction equation

HRID 1700302 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]([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:27])[NH2:26])[CH:19]=3)=[CH:10][C:9]=2[C:35]([F:38])([F:37])[F:36])[CH2:3][CH2:2]1.[C:39](Cl)(=[O:41])[CH3:40].CCN(CC)CC.[Li+].[OH-]>CC#N.O>[C:39]([N: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:35]([F:36])([F:37])[F:38])[CH2:3][CH2:2]1)(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 136364259HCID 136364259, compound

Product 1

HCID 136364262HCID 136364262, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(carboxy)ethylcarbonyl)-N-(3-(6-hydroxy-3-amidinophenyl)prop-2-en-1-yl)benzenamine (400 mg) in 100 mL CH3CN was added acetyl chloride (500 mg) and Et3N (1.28 g) at ambient temperature. The resulting solution was stirred at ambient temperature for 2 hours. LiOH (500 mg) in water (1.0 mL) was then added to the reaction mixture and the resulting reaction mixture was stirred at ambient temperature for 2 hours. Acidification with trifluoroacetic acid, concentration, purification on HPLC (H2O/CH3CN, gradient) and freeze-drying afforded 4-(N′-(acetyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(carboxy)ethylcarbonyl)-N-(3-(6-hydroxy-3- amidinophenyl)prop-2-en-1-yl)benzenamine.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at ambient temperature for 2 hours
  3. concentrationAcidification with trifluoroacetic acid, concentration, purification on HPLC (H2O/CH3CN, gradient)
  4. customfreeze-drying

Sources & evidence

ORD record
ord-d9c14a5fab4445eba4e0dfc62ec0aa0e
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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