Diisopropylethylamine → HCID 59643195, compound

HRID 2251531Notes

Reaction equation

HRID 2251531 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[C:31]1[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[CH:33][N:32]=1.CCN(C(C)C)C(C)C>>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:32][CH:33]=1)(=[O:39])[CH3:38]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 59643115HCID 59643115, compound

Product 1

HCID 59643195HCID 59643195, compoundYield 35.3%

Procedure

A mixture of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (1.05 g; 2.57 mmol), 2-chloro-5-acetyl-pyridine (0.40 g; 2.57 mmol) and DIEA (0.36 g; 2.83 mmol) was heated in a pressure tube at 180C for 5 hr. Upon cooling, the residue was chromatographed using 20% ethyl acetate-hexane mixtures to afford ethyl 2-[4-(2-{(5-acetylpyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (0.48 g; 35% yield).

Workup

  1. temperatureUpon cooling
  2. customthe residue was chromatographed

Sources & evidence

ORD record
ord-73805e3771a04161804399cb8cd09276
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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