Diethylamine → 1-[6-(Diethylamino)pyrazin-2-yl]-1H-benzimidazol-6-amine

HRID 2192689Notes

Reaction equation

HRID 2192689 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[N:4][CH:3]=1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].CCN(C(C)C)C(C)C>C(OC(O)C)C>[CH2:18]([N:20]([CH2:21][CH3:22])[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[N:4][CH:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 582170941-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine

Product 1

HCID 582171581-[6-(Diethylamino)pyrazin-2-yl]-1H-benzimidazol-6-amine

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A solution of 1-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine (100 mg, 0.41 mmol) and diethylamine (430 μL, 4.1 mmol) in ethoxyethanol (2 mL) containing DIPEA (140 μL) was heated in a sealed tube overnight under N2. The solution was concentrated under reduced pressure and the residue dissolved in EtOAc (20 mL) and washed successively with H2O (20 mL) and brine (20 mL). After drying (Na2SO4) the solvent was removed under reduced pressure and the residue chromatographed eluting with dichloromethane-methanol (9:1-94:6) to separate pure product from the lower fractions (110 mg).

Workup

  1. temperaturewas heated in a sealed tube overnight under N2
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in EtOAc (20 mL)
  4. washwashed successively with H2O (20 mL) and brine (20 mL)
  5. dry with materialAfter drying (Na2SO4) the solvent
  6. customwas removed under reduced pressure
  7. customthe residue chromatographed
  8. washeluting with dichloromethane-methanol (9:1-94:6)
  9. customto separate pure product from the lower fractions (110 mg)

Sources & evidence

ORD record
ord-b9d14e463c714b37bda605157a403d9c
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

Loading…