HCID 71246520, compound → HCID 86727919, compound

HRID 1519103Notes

Reaction equation

HRID 1519103 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:32])([CH3:31])[C:15]([NH:17][CH:18]1[CH:25]2[CH2:26][C:21]3([C:28]([NH2:30])=[O:29])[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)[CH2:24]2)=[O:16])(=[O:12])=[O:11])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:32])([CH3:31])[C:15]([NH:17][CH:18]1[CH:25]2[CH2:26][C:21]3([C:28]([NH2:30])=[O:29])[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)[CH2:24]2)=[O:16])(=[O:11])=[O:12]

Participants

4

Reactant 1

HCID 71246520HCID 71246520, compound

Product 1

HCID 86727919HCID 86727919, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ina 25-mL flask, 4-[2-(2-nitro-benzenesulfonylamino)-2-methyl-propionylamino]-adamantane-1-carboxylic acid amide (30 mg, 0.0645 mmol) and methanol (5 mL) were charged and dissolved, and 5% Pd/c (10 mg) was added thereto. The reaction vessel was degassed under reduced pressure, and filled with hydrogen. At room temperature, through stirring for 3 hours, the reaction was completed. Then, through celite filtering, Pd was removed. At 35° C., through vacuum evaporation, 4-[2-(2-amino-benzenesulfonylamino)-2-methyl-propionylamino]-adamantane-1-carboxylic acid amide (21 mg, 75.0%) was obtained.

Workup

  1. dissolutiondissolved
  2. customThe reaction vessel was degassed under reduced pressure
  3. additionfilled with hydrogen
  4. customThen, through celite filtering, Pd was removed
  5. customAt 35° C., through vacuum evaporation

Sources & evidence

ORD record
ord-cc69b483b8304538bdb9237c54f622ff
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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