18-Crown-6 → HCID 131735460, compound

HRID 632789Notes

Reaction equation

HRID 632789 reaction equation
CS(O[CH:6]1[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]([C:14]2[C:18]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:27]4[CH:32]=[CH:31][N:30]=[C:29]([N:33]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34][C:35]([F:38])([F:37])[F:36])[CH:28]=4)[O:25][CH:26]=3)=[O:21])=[CH:17][N:16]([CH3:46])[N:15]=2)[CH2:7]1)(=O)=O.[N-:47]=[N+:48]=[N-:49].[Na+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.C(OCC)(=O)C>[N:47]([CH:6]1[CH2:7][N:8]([C:14]2[C:18]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:27]4[CH:32]=[CH:31][N:30]=[C:29]([N:33]([CH2:34][C:35]([F:37])([F:38])[F:36])[C:39](=[O:40])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:28]=4)[O:25][CH:26]=3)=[O:21])=[CH:17][N:16]([CH3:46])[N:15]=2)[C:9](=[O:13])[C:10]1([CH3:12])[CH3:11])=[N+:48]=[N-:49]

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 33557Sodium AzideHCID 118061557HCID 118061557, compound

Product 1

HCID 131735460HCID 131735460, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-(((2-(2-((tert-Butoxycarbonyl)(2,2,2-trifluoroethyl)amino)pyridin-4-yl)-1,3-oxazol-4-yl)carbonyl)amino)-1-methyl-1H-pyrazol-3-yl)-4,4-dimethyl-5-oxopyrrolidin-3-yl methanesulfonate (15 mg) was dissolved in DMF (0.50 mL), sodium azide (22 mg) and 18-crown-6 (5.9 mg) were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed three times with saturated aqueous ammonium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.0 mg).

Workup

  1. washthe mixture was washed three times with saturated aqueous ammonium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-adbe367cbe294750bed8f57efd70c12f
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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