1,4-Dioxane hydrochloride → 2-[(4-{2-[(5-Bromopyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid hydrochloride

HRID 914426Notes

Reaction equation

HRID 914426 reaction equation
C([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.[ClH:34].O1CCOCC1>O1CCOCC1>[ClH:34].[Br:32][C:29]1[CH:30]=[CH:31][C:26]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:33])=[O:5])[S:12][CH:13]=2)=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 597594422-[(4-{2-[(5-Bromopyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 673983692-[(4-{2-[(5-Bromopyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[(4-{2-[(5-Bromopyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (1.72 g) synthesized in Example 293-1 was dissolved in dioxane (5 mL), 4 mol/L hydrochloric acid-dioxane (25 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, azeotroped with diethyl ether, and the precipitated solid was collected by filtration to give the title compound (1.0 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customazeotroped with diethyl ether
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ee304994f2ed4b4385f2ac823cde31d9
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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