HCID 19374868, compound → HCID 19374916, compound

HRID 128697Notes

Reaction equation

HRID 128697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:14]([CH2:23][CH2:24][CH3:25])[CH:15]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH3:16])[S:11][C:12]=2[CH3:13])=[C:4]([O:26]C)[CH:3]=1>Br>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:14]([CH2:23][CH2:24][CH3:25])[CH:15]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[CH3:16])[S:11][C:12]=2[CH3:13])=[C:4]([OH:26])[CH:3]=1

Participants

3

Reactant 1

HCID 19374868HCID 19374868, compound

Product 1

HCID 19374916HCID 19374916, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Bring to reflux for 24 hours 700 mg of 4-(4-chloro-2-methoxyphenyl)-5-methyl-2-{N-propyl-N-[1-(4-pyridyl)ethyl]amino}thiazole, the compound of Example 22, dissolved in 30 ml of concentrated hydrobromic acid. Evaporate to dryness and take up the residue in Water saturated with potassium carbonate. Extract with methylene chloride and then evaporate off the organic solvent. Purify the residue by chromatography on a silica column, using a mixture of ethyl acetate and methanol (9:1 V/V) as eluent, to obtain the expected product in the form of an oil.

Workup

  1. customEvaporate to dryness
  2. extractionExtract with methylene chloride
  3. customevaporate off the organic solvent
  4. customPurify the residue by chromatography on a silica column
  5. additiona mixture of ethyl acetate and methanol (9:1 V/V) as eluent

Sources & evidence

ORD record
ord-3d6fcc0493bb481cb6a1004c13920a3f
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

Loading…