Dimethylformamide → HCID 23070686, compound

HRID 501429Notes

Reaction equation

HRID 501429 reaction equation
CN(C)C=O.[F:6][C:7](I)([F:9])[F:8].[CH2:11]([N:15]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH:25]=[O:26])[N:17]=[C:16]1[N:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1)[C:12]#[C:13][CH3:14].[Cl-].[NH4+]>[Zn].C(OCC)(=O)C>[CH2:11]([N:15]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH:25]([OH:26])[C:7]([F:9])([F:8])[F:6])[N:17]=[C:16]1[N:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:29][CH2:28]1)[C:12]#[C:13][CH3:14]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 16843TrifluoroiodomethaneHCID 25517Ammonium ChlorideHCID 23070982HCID 23070982, compound

Product 1

HCID 23070686HCID 23070686, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.065 g of zinc and a 2 ml N,N-dimethylformamide solution of 0.200 g of trifluoromethyl iodide were added to a 3 ml N,N-dimethylformamide solution of 0.155 g of t-butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-formyl-1H-imidazol-2-yl]piperazine-1-carboxylate under a nitrogen atmosphere, and the mixture was stirred under sonication for 30 minutes. 30 ml of ethyl acetate and 30 ml of a 5% ammonium chloride solution were added to the mixture. The organic layer was washed twice with 20 ml of water and then with 20 ml of a saturated sodium chloride solution, and dried over magnesium sulfate. The organic liquid was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.013 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:9).

Workup

  1. washThe organic layer was washed twice with 20 ml of water
  2. dry with materialwith 20 ml of a saturated sodium chloride solution, and dried over magnesium sulfate
  3. concentrationThe organic liquid was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8db4037063da43f6be9becd4b9ea3fa3
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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