Hydrochloric Acid → HCID 178488936, compound

HRID 925954Notes

Reaction equation

HRID 925954 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19]CC3C=CC(OC)=CC=3)[C:16]3[C:11](=[C:12]([CH3:31])[CH:13]=[C:14]([O:29][CH3:30])[CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[Cl-].[Cl-].[Cl-].[Cs+].[Cs+].[Cs+].[I-].[Na+].Cl>C(#N)C.O>[OH:19][C:17]1[C:16]2[C:11](=[C:12]([CH3:31])[CH:13]=[C:14]([O:29][CH3:30])[CH:15]=2)[N:10]=[C:9]([C:6]2[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 20975861Cesium trichlorideHCID 666508822-(4-Isopropyl-thiazol-2-yl)-6-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-quinoline

Product 1

HCID 178488936HCID 178488936, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 222f (1.23 g, 2.82 mmol), cesium trichloride (1.58 g, 4.23 mmol), and sodium iodide (423 mg, 2.82 mmol) in ACN (26 mL) were stirred at 85° C. for 1 hr. The mixture was then filtered through celite and the solvent was evaporated. The brown solid obtained was suspended in water, pH was adjusted at 5 with 1N HCl. The mixture was extracted with DCM, dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (petroleum ether/DCM) to yield compound 218f as a brown solid in 55% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.40 (d, J=6.91 Hz, 6H), 2.80 (s, 3H), 3.17-3.24 (m, 1H), 3.89 (s, 3H), 7.00 (s, 1H), 7.21 (m, 1H), 7.55 (s, 1H), 7.79 (s, 1H), 9.56 (brs, 1H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. customthe solvent was evaporated
  3. customThe brown solid obtained
  4. extractionThe mixture was extracted with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography on silica gel (petroleum ether/DCM)

Sources & evidence

ORD record
ord-c34fafa2ea2944dbaff1ef08687a4698
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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