Acetic Acid → HCID 178496098, compound

HRID 1893697Notes

Reaction equation

HRID 1893697 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[N:14]=[C:15]([NH:18][CH:19]([CH3:21])[CH3:20])[S:16][CH:17]=2)=O)=[C:8]([Cl:22])[C:7]([O:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].CC(O)=O>C1(C)C=CC=CC=1.O>[Cl:22][C:8]1[C:7]([O:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27])=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([C:13]1[N:14]=[C:15]([NH:18][CH:19]([CH3:21])[CH3:20])[S:16][CH:17]=1)[CH:2]=[C:1]2[OH:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 577850662-Isopropylaminothiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxyethoxy)phenyl]amide

Product 1

HCID 178496098HCID 178496098, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Isopropylamino-thiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide (18 g, 40.7 mmol) was suspended in toluene (400 ml). NaH (2.4 g, 61 mmol) was added to the vigorously stirred mixture while monitoring H2 evolution. The mixture became a clear solution during heating to reflux. After refluxing for 3 h, the mixture was cooled to room temperature. A solution of AcOH (69.2 mmol) in H2O (3 vol) was added to the mixture. After vigorous agitation for 1 h at 0° C., the solids were collected by filtration and rinsed with H2O. The wet cake was dried under high vacuum to a constant weight to provide 8-chloro-7-(2,2-dimethoxy-ethoxy)-2-(2-isopropylaminothiazol-4-yl)-quinolin-4-ol (15 g, 86% yield).

Workup

  1. temperatureduring heating to reflux
  2. temperatureAfter refluxing for 3 h
  3. filtrationthe solids were collected by filtration
  4. washrinsed with H2O
  5. customThe wet cake was dried under high vacuum to a constant weight

Sources & evidence

ORD record
ord-03b9225ccc8f4ce784011d265f5a2d83
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

Loading…