Hydrochloric Acid → HCID 178496099, compound

HRID 1422530Notes

Reaction equation

HRID 1422530 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N: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[S:14][CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1)[CH:2]=[C:1]2[OH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 672246774-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide

Product 1

HCID 178496099HCID 178496099, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide (2.20 g, 5.16 mmol) and KOtBu (1.22 g, 10.84 mmol) were dissolved in tBuOH (50 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-(4-isopropyl-thiazol-2-yl)-quinolin-4-ol (2.11 g, 99%) 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-5235c45c84164982a29f96adf630ff6e
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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