HCID 58709968, compound → HCID 58709843, compound

HRID 2375905Notes

Reaction equation

HRID 2375905 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1>CO.[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[C:10]1[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 58709968HCID 58709968, compound

Product 1

HCID 58709843HCID 58709843, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl-{2-[2-(3-nitrophenyl)imidazol-1-yl]ethyl}amine (88 mg, 0.34 mmol) in methanol (5 mL) was hydrogenated in the presence of 10% Pd/C (80 mg) for 16 h. The reaction mixture was filtered through a Celite pad. The filtrate was concentrated in vacuo to afford the title compound, which was used directly in the next step without purification. 1H-NMR (CDCl3, 400 MHz): δ=2.23 (s, 6H), 2.63 (t, J=7.2 Hz, 2H), 4.13 (d, J=7.2 Hz, 2H), 6.72-6.75 (m, 1H), 6.90-6.92 (m, 1H), 6.96 (t, J=2.0 Hz, 1H), 7.08 (d, J=1.2 Hz, 1H), 7.11 (d, J=1.2 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H). MS (ES+): m/z 231.22 [MH+]. HPLC: tR=0.33 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-28d668ccd9bf463da800311f1a5ad6c1
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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