Sodium hydride → HCID 66558549, compound

HRID 2172249Notes

Reaction equation

HRID 2172249 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]([CH2:12][CH2:13][CH:14]([OH:41])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([O:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1.[Cl-].[NH4+]>CN(C)C=O>[N+:9]([C:7]1[N:8]=[C:4]2[N:5]([CH:6]=1)[CH2:12][CH2:13][CH:14]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([O:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)=[CH:19][CH:18]=1)[O:41]2)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70874334HCID 70874334, compound

Product 1

HCID 66558549HCID 66558549, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (70 mg) was added to an N,N-dimethylformamide solution (10 ml) of 4-(2-chloro-4-nitroimidazol-1-yl)-1-{4-[4-(4-trifluoromethoxyphenoxy)piperidin-1-yl]phenoxy}butan-2-ol (0.9 g) under ice cooling, and the mixture was stirred at room temperature for 3 days. A saturated ammonium chloride aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (methylene chloride:ethyl acetate=8:2→methylene chloride:ethyl acetate=2:8) and recrystallized from methylene chloride-ethyl acetate-isopropyl ether to afford the title compound as a pale yellow powder (158 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtering
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (methylene chloride:ethyl acetate=8:2→methylene chloride:ethyl acetate=2:8)
  8. customrecrystallized from methylene chloride-ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-6af12fbbb3e04ee8804fd3606746f2bb
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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