Tetrahydrofuran → HCID 59110205, compound

HRID 1169611Notes

Reaction equation

HRID 1169611 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=1)[CH3:2].C1COCC1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([N:34]2[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]2)[CH:7]=1)[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 87464184HCID 87464184, compound

Product 1

HCID 59110205HCID 59110205, compound

Procedure

To a solution of compound of step d) (0.5 g, 1.36 mmol) in dry THF (10 ml) K3PO4 (405 mg, 1.90 mmol), N-methylpiperazine (180 μl, 163 mmol), tris(dibenzylideneacetoneacetone)-dipalladium(0) (60 mg, 0.07 mmol) and 2-(di-t-butylphosphino)biphenyl (21 mg, 0.07 mmol) are added under argon. The reaction is kept under argon at 80° C. for 24 hours. After filtration DMF is removed under reduced pressure and the crude residue is purified on silica gel (methylene chloride/methanol 95/5) affording the pure compound.

Workup

  1. filtrationAfter filtration DMF
  2. customis removed under reduced pressure
  3. customthe crude residue is purified on silica gel (methylene chloride/methanol 95/5)
  4. customaffording the pure compound

Sources & evidence

ORD record
ord-bad5d137d80c410cbb488a599746f1f0
Source dataset
uspto-grants-2010_11
Patent number
US07825124B2

Reaction notes

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