Isopropylamine → 1-[6-(Isopropylamino)pyrazin-2-yl]-1H-benzimidazol-6-amine

HRID 2192688Notes

Reaction equation

HRID 2192688 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.[CH:18]([NH2:21])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C>C(OC(O)C)C>[CH:18]([NH:21][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)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 582170941-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine

Product 1

HCID 597839311-[6-(Isopropylamino)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 isopropylamine (350 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 (102 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 (102 mg)

Sources & evidence

ORD record
ord-2b1cfcc982b140b98aa1ecde0a218559
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

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