m-Toluidine → HCID 2755428, compound

HRID 1685489Notes

Reaction equation

HRID 1685489 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1>C(Cl)Cl.Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:18][C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)=[O:9])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 151496716-Chloropyrazine-2-carbonyl chloride

Product 1

HCID 2755428HCID 2755428, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 15B (950 mg, 5.37 mmol) was dissolved in CH2Cl2 (20 mL). Triethylamine (1.10 mL, 7.89 mmol) and m-toluidine (0.70 mL, 6.46 mmol) were added, and the reaction stirred at ambient temperature for 2 h. The reaction mixture was diluted with 0.1M HCl (100 mL) and extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, washed with brine (50 mL), dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (2.5% EtOAc in CH2Cl2, Rf=0.39) to afford the title compound as a white solid (1.11 g, 83%). MS (DCI/NH3) m/z 248 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography (2.5% EtOAc in CH2Cl2, Rf=0.39)

Sources & evidence

ORD record
ord-5b0323b277c641eab7d6eca56272b0e7
Source dataset
uspto-grants-2012_04
Patent number
US08148408B2

Reaction notes

Loading…