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

HRID 563720Notes

Reaction equation

HRID 563720 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-3c46a7bfedab4e9e9a82159f0e799851
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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