HCID 86687894, compound → HCID 70114149, compound

HRID 868942Notes

Reaction equation

HRID 868942 reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]=[C:7]1[CH2:17][NH:18]C(=O)OCC1C=CC=CC=1)(=[O:5])=[O:4]>CN(C=O)C.[Pd]>[NH2:18][CH2:17][C:7]1[N:6]([S:3]([N:2]([CH3:29])[CH3:1])(=[O:4])=[O:5])[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]=1

Participants

4

Reactant 1

HCID 86687894HCID 86687894, compound

Product 1

HCID 70114149HCID 70114149, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Benzyl (1-(N,N-dimethylsulfamoyl)-4-phenyl-1H-imidazol-2-yl)methylcarbamate (235 mg, 0.56 mmol) was dissolved in anhydrous DMF (5 mL) and Pd on carbon (about 5 mg, catalytic) was added. The vessel containing the solution was purged with H2, and the vessel was sealed. A H2 balloon was attached. Another 10 mg of Pd on carbon was added after 8 h, and the suspension was stirred at room temperature for 48 hours (total). The suspension was filtered through Celite, washing with EtOAc (30 mL), and the washes were concentrated to give crude 2-(aminomethyl)-N,N-dimethyl-4-phenyl-1H-imidazole-1-sulfonamide.

Workup

  1. additionThe vessel containing the solution
  2. customwas purged with H2
  3. customthe vessel was sealed
  4. additionAnother 10 mg of Pd on carbon was added after 8 h
  5. filtrationThe suspension was filtered through Celite
  6. washwashing with EtOAc (30 mL)
  7. concentrationthe washes were concentrated

Sources & evidence

ORD record
ord-28719ca3bba74009b4b57e3674dc8e3c
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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