Imidazole → HCID 18712878, compound

HRID 392498Notes

Reaction equation

HRID 392498 reaction equation
[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([CH2:18]OS(C)(=O)=O)[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>CN(C=O)C>[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([CH2:18][N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 21978370(1-Benzhydrylazetidin-3-yl)methyl methanesulfonate

Product 1

HCID 18712878HCID 18712878, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of the title compound from Step C (2.3 g, 6.95 mmoles) in DMF (15 mL) was added to a stirred solution of NaH (0.25 g, 10.42 mmoles) and imidazole (0.71 g, 10.44 mmoles) in DMF (10 mL) under nitrogen atmosphere. The mixture was stirred at 60° C. for 16 h. DMF was evaporated in vacuo. The resulting crude product was extracted with CH2Cl2 and the extract was successively washed with water and brine, and the CH2Cl2 was evaporated to leave the title compound (2.1 g, 100%). FABMS (M+1)=304.

Workup

  1. customDMF was evaporated in vacuo
  2. extractionThe resulting crude product was extracted with CH2Cl2
  3. washthe extract was successively washed with water and brine
  4. customthe CH2Cl2 was evaporated

Sources & evidence

ORD record
ord-8e423761bcba455d9f20e5e36efd9d63
Source dataset
uspto-grants-2004_10
Patent number
US06800636B2

Reaction notes

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