HCID 86704206, compound → HCID 62139373, compound

HRID 624001Notes

Reaction equation

HRID 624001 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][N:9]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[N:10]2)[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[N:3]=1>[Pd].CO>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][N:9]2[CH:13]=[C:12]([NH2:14])[CH:11]=[N:10]2)[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 86704206HCID 86704206, compound

Product 1

HCID 62139373HCID 62139373, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask was added 2-methyl-1-(2-(4-nitro-1H-pyrazol-1-yl)-ethyl)-1H-benzoimidazole (5.23 g, 19.28 mmol), Pd/C (523 mg) and MeOH (100 mL, degassed). The flask was evacuated and backfilled with H2 and the reaction mixture was stirred under H2-atmosphere at rt for 5 h. The reaction mixture was filtered over celite, washed with MeOH and the solvent was removed under reduced pressure. Purification was performed by dissolving the desired compound at 40° C. in DCM (60 mL) and filtering off the insoluble impurities. By adding heptane (150 mL) to the remaining solution, the title compound precipitated out as a pink solid. LC-MS conditions B: tR=0.17 min, [M+H]+=242.00.

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction mixture was filtered over celite
  3. washwashed with MeOH
  4. customthe solvent was removed under reduced pressure
  5. customPurification
  6. dissolutionby dissolving the desired compound at 40° C. in DCM (60 mL)
  7. filtrationfiltering off the insoluble impurities
  8. additionBy adding heptane (150 mL) to the remaining solution
  9. customthe title compound precipitated out as a pink solid

Sources & evidence

ORD record
ord-6250a432e79c4075ba976a5e6a429cb3
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

Loading…