1-((1-Acetylpiperidin-4-yl)methyl)-3-(2-nitro-5-(thiophen-2-yl)phenyl)urea → 1-((1-Acetylpiperidin-4-yl)methyl)-3-(2-amino-5-(thiophen-2-yl)phenyl)urea

HRID 2201701Notes

Reaction equation

HRID 2201701 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=[CH:17][C:16]=2[N+:26]([O-])=O)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=[CH:17][C:16]=2[NH2:26])=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 709818821-((1-Acetylpiperidin-4-yl)methyl)-3-(2-nitro-5-(thiophen-2-yl)phenyl)urea

Product 1

HCID 867125331-((1-Acetylpiperidin-4-yl)methyl)-3-(2-amino-5-(thiophen-2-yl)phenyl)ureaYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-((1-acetylpiperidin-4-yl)methyl)-3-(2-nitro-5-(thiophen-2-yl)phenyl)urea (0.09 g, 0.22 mmol) in methanol was added Pd/C (0.03 g, 0.028 mmol, 1.2 equiv.). The reaction mixture was degassed then stirred at room temperature under H2 atmosphere for 1 h. The reaction was filtered through celite and concentrated. The crude solid was washed with ether, and dried under reduced pressure to obtain of pure 1-((1-acetylpiperidin-4-yl)methyl)-3-(2-amino-5-(thiophen-2-yl)phenyl)urea (0.05 g, 60% yield). ESI+ MS: m/z 373 ([M]+). 1H NMR (500 MHz, d6-DMSO): δ 7.66 (d, J=2.0 Hz, 1H), 7.58 (s, 1H), 7.33 (d, J=5.0 Hz, 1H), 7.17 (d, J=3.5 Hz, 1H), 7.10 (dd, J=3.5 Hz, 1H), 7.04-7.02 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 6.31 (t, J=6.0 Hz, 1H), 4.89 (bs, 2H), 4.36 (d, J=13.0 Hz, 1H), 3.81 (d, J=13.5 Hz, 1H), 3.0-2.96 (m, 3H), 1.90 (s, 3H), 1.71-1.64 (m, 3H), 1.10-1.07 (m, 1H), 0.98-0.95 (m, 1H).

Workup

  1. customThe reaction mixture was degassed
  2. filtrationThe reaction was filtered through celite
  3. concentrationconcentrated
  4. washThe crude solid was washed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-bbb1b76833e04f19ad2fbbe28130e9af
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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