Diisopropylethylamine → (2'-{[Ethyl-(5-methyl-benzooxazol-2-yl)-amino]-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 1810480Notes

Reaction equation

HRID 1810480 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][NH:25][CH2:26][CH3:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].Cl[C:30]1[O:31][C:32]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:33]=2[N:34]=1.C(N(C(C)C)CC)(C)C>CCO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:26][CH3:27])[C:30]2[O:31][C:32]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:33]=3[N:34]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99896072-Chloro-5-methyl-1,3-benzoxazoleHCID 66604101(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66607250(2'-{[Ethyl-(5-methyl-benzooxazol-2-yl)-amino]-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

(2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.300 g, 0.76 mmol), chloro-5-methyl-benzooxazole (0.135 g, 0.81 mmol), and diisopropylethylamine (0.5 mL, 2.87 mmol) were combined in EtOH (2 mL) in a sealed tube, and the reaction was stirred at 80° C. for 8 hours. The mixture was concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6dd6439869684b26917395aa9a0a01a5
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

Loading…