Ethylene Glycol → HCID 23030552, compound

HRID 1869581Notes

Reaction equation

HRID 1869581 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5](Cl)=[N:6][CH:7]=[C:8]([CH:35]=1)[C:9]([NH:11][C:12]1[S:13][C:14]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[C:15]([C:17]2[S:18][CH:19]=[C:20]([Cl:22])[CH:21]=2)[N:16]=1)=[O:10].C(Cl)(Cl)Cl.[CH2:41]([OH:44])[CH2:42][OH:43]>>[ClH:3].[Cl:3][C:4]1[C:5]([O:43][CH2:42][CH2:41][OH:44])=[N:6][CH:7]=[C:8]([CH:35]=1)[C:9]([NH:11][C:12]1[S:13][C:14]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[C:15]([C:17]2[S:18][CH:19]=[C:20]([Cl:22])[CH:21]=2)[N:16]=1)=[O:10]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 6212ChloroformHCID 24758Sodium hydrideHCID 23030584HCID 23030584, compound

Product 1

HCID 23030552HCID 23030552, compound

Procedure

To a solution of 48 mg of 40% sodium hydride in 1 ml of ethyleneglycol, 100 mg of the compound of Example 5 was added at room temperature, the temperature was elevated to 50° C., and the mixture was stirred for 4 days. To the reaction solution, chloroform was added, and the organic layer was washed with saturated aqueous NaHCO3 and brine and dried over sodium sulfate. After the evaporation of the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform-MeOH=200:1˜20:1) and the obtained compound was dissolved in 5 ml of EtOAc, 0.8 ml of 0.1M HCl-EtOAc solution was added thereto, and the mixture was stirred for a while. Then, the solvent was evaporated under reduced pressure, and the residue was washed with diethylether to obtain 34 mg of 5-chloro-N-[4-(4-chlorothiophen-2-yl)-5-(4-cyclohexylpiperazin-1-yl)thiazol-2-yl]-6-(2-hydroxyethoxy)nicotinamide hydrochloride.

Workup

  1. customwas elevated to 50° C.
  2. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over sodium sulfate
  4. customAfter the evaporation of the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform-MeOH=200:1˜20:1)
  6. dissolutionthe obtained compound was dissolved in 5 ml of EtOAc
  7. addition0.8 ml of 0.1M HCl-EtOAc solution was added
  8. stirringthe mixture was stirred for a while
  9. customThen, the solvent was evaporated under reduced pressure
  10. washthe residue was washed with diethylether

Sources & evidence

ORD record
ord-b8a76f3f93fd4c2285b9dfa3d6464925
Source dataset
uspto-grants-2009_12
Patent number
US07638536B2

Reaction notes

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