Hydrochloric Acid → HCID 178496097, compound

HRID 1422525Notes

Reaction equation

HRID 1422525 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[N:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[S:16][CH:17]=2)=O)=[C:8]([Cl:21])[C:7]([O:22][CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC([O-])(C)C.[K+].Cl>CC(O)(C)C>[Cl:21][C:8]1[C:7]([O:22][CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([C:13]1[N:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[S:16][CH:17]=1)[CH:2]=[C:1]2[OH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 672240522-Isopropyl-thiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide

Product 1

HCID 178496097HCID 178496097, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

2-Isopropyl-thiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide (5.5 g, 12.91 mmol) and KOtBu (3.04 g, 27.11 mmol) were dissolved in tBuOH (100 mL) under an atmosphere of nitrogen. The reaction was heated to 75° C. for 4 hours. The reaction was cooled to rt and the pH was adjusted to 4 with 2N HCl(aq). The reaction mixture was concentrated and taken up in EtOAc (100 mL). The mixture was washed with ½ sat. brine. The organic layer was dried with Na2SO4, filtered and was concentrated. 8-Chloro-7-(2,2-dimethoxy-ethoxy)-2-(2-isopropyl-thiazol-4-yl)-quinolin-4-ol (4.49 g, 85%) was isolated by silica gel chromatography as a yellow solid.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationThe reaction mixture was concentrated
  3. washThe mixture was washed with ½ sat. brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-d0b9d0890a0c4208b0d7f883c011e030
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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