Ethanolamine → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethylamino]-ethanol

HRID 495718Notes

Reaction equation

HRID 495718 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([Si:9]([CH3:32])([CH3:31])[O:10][C@H:11]([C:24]1[CH:25]=[N:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O)([CH3:8])([CH3:7])[CH3:6].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CS(C)=O>[C:5]([Si:9]([CH3:31])([CH3:32])[O:10][CH:11]([C:24]1[CH:25]=[N:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:12][NH:4][CH2:3][CH2:1][OH:2])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 12972452(R)-Toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester

Product 1

HCID 223265992-[2-(Tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethylamino]-ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethanolamine (1.2 mL), (R)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester (2.2 g) and diisopropylethylamine (1.3 mL) in DMSO (5 mL) was heated at 80° C. for 4 h. After cooling, the reaction solution was diluted into ethyl acetate, washed with water (2×), brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (I-3a) as an oil.

Workup

  1. temperatureAfter cooling
  2. washwashed with water (2×), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36517c098c754ee08dfc6692c91367f0
Source dataset
uspto-grants-2005_09
Patent number
US06939867B2

Reaction notes

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