2-nitro-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide → 2-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide

HRID 926760Notes

Reaction equation

HRID 926760 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=[O:7])([O-])=O>CCOC(C)=O.CCO.[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:13][CH:14]=1)=[O:7]

Participants

4

Reactant 1

HCID 665869372-nitro-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide

Product 1

HCID 665870272-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of 2-nitro-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide (100 mg, 0.25 mmol, 1.00 equiv) in EtOAc/EtOH (5/5 mL). The mixture was treated with Pd/C (10 mg) and stirred under a hydrogen atmosphere for 2 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 90 mg (97%) of product as a yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-2715ca01338d4a24bd73693f80c7dea0
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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