Methyl iodide → HCID 58561871, compound

HRID 2167354Notes

Reaction equation

HRID 2167354 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)(=[O:8])=[O:7])[N:3]=[N:2]1.[C:22]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:22][N:1]1[CH:5]=[C:4]([S:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)(=[O:8])=[O:7])[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178452407HCID 178452407, compound

Product 1

HCID 58561871HCID 58561871, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution tert-butyl 4-(1H-1,2,3-triazol-4-ylsulfonyl)piperazine-1-carboxylate (0.54 g, 1.15 mmol) in DMF (10 mL) at 0° C. was added K2CO3 (0.32 g, 2.30 mmol) followed by MeI (0.09 mL, 1.49 mmol) drop wise. Then the reaction mixture was stirred at room temperature for 16 hours. Then the reaction mixture was concentrated under reduced pressure and dissolved in CH2Cl2 (20 mL), washed with H2O (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 12 g Redisep column, 9:1 mixture of CH2Cl2/CH3OH) to give tert-butyl 4-(1-methyl-1H-1,2,3-triazol-4-ylsulfonyl)piperazine-1-carboxylate as a white foam (32, 0.30 g, 57%): MS (ESI+) m/z 332.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in CH2Cl2 (20 mL)
  3. washwashed with H2O (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 12 g Redisep column, 9:1 mixture of CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-7ffedcf6ecb14c07aceb3b4097b988db
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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