Hydrochloric Acid → HCID 45139060, compound

HRID 554663Notes

Reaction equation

HRID 554663 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23]([C:26](=[O:35])[CH2:27][C:28]2[CH:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[CH2:24][CH3:25])[CH:11]=1)C.[Li+].[OH-].Cl>C1COCC1>[Cl:34][C:31]1[N:30]=[CH:29][C:28]([CH2:27][C:26]([N:23]([CH2:22][C:13]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:12]=2[C:10]2[CH:11]=[C:6]([CH2:5][C:4]([OH:36])=[O:3])[CH:7]=[N:8][CH:9]=2)[CH2:24][CH3:25])=[O:35])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86640543{5-[2-({N-[2-(6-chloro-pyridin-3-yl)-acetyl]-N-ethyl-amino}-methyl)-4-trifluoromethyl-phenyl]-pyridin-3-yl}-acetic acid ethyl ester

Product 1

HCID 45139060HCID 45139060, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To {5-[2-({N-[2-(6-chloro-pyridin-3-yl)-acetyl]-N-ethyl-amino}-methyl)-4-trifluoromethyl-phenyl]-pyridin-3-yl}-acetic acid ethyl ester (0.085 g, 0.16 mmol) in THF (2 mL) was added 1N aqueous LiOH (2 mL), and the reaction was stirred at 50° C. The mixture was neutralized with 1N aqueous HCl to pH 3-4 and extracted three times with EtOAc. The combined organic layers were dried and concentrated to give Compound 31.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-53c011bf1868434e96b41656f9d13a8f
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

Loading…