HCID 10266165, compound → HCID 10244311, compound

HRID 1784961Notes

Reaction equation

HRID 1784961 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([N+:19]([O-])=O)[C:12]=3[N:11]=2)=[O:9])[CH2:4][CH2:3]1.[H][H]>C1COCC1.C(O)C.[Pd]>[NH2:19][C:18]1[C:12]2[N:11]=[C:10]([C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[O:9])[NH:14][C:13]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 10266165HCID 10266165, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10244311HCID 10244311, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolCatalyst

Procedure

To a solution of (4-methyl-piperazin-1-yl)-(4-nitro-1H-benzoimidazol-2-yl)-methanone (640 mg, 2.21 mmol) in 1:1 THF/ethanol (10 mL, with a few drops of ethyl acetate) was added 10% palladium on carbon (640 mg). The reaction mixture was placed under 1 atm hydrogen for 72 h. The resulting mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure. The crude product was purified on silica gel (40 g; 0-10% methanol/CH2Cl2) to afford 519 mg (91%) of the title compound. MS (ESI): mass calculated for C13H17N5O, 259.31; m/z found, 260.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 12.21-11.36 (s, 1H), 7.12 (t, J=7.8 Hz, 1H), 6.94-6.83 (m, 1H), 6.53 (d, J=7.8 Hz, 1H), 4.82-4.78 (m, 2H), 4.43-4.40 (m, 2H), 3.94-3.92 (m, 2H), 2.56-2.54 (m, 4H), 2.35 (s, 3H).

Workup

  1. filtrationThe resulting mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified on silica gel (40 g; 0-10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-687876fd9504433f8e40399fa283c6f1
Source dataset
uspto-grants-2009_03
Patent number
US07504426B2

Reaction notes

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