Triphenylphosphine → HCID 3010647, compound

HRID 2229332Notes

Reaction equation

HRID 2229332 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH:15]1([N:18]2[C:24]3[N:25]=[CH:26][C:27]([CH2:29][CH2:30][OH:31])=[CH:28][C:23]=3[C:22](=[O:32])[NH:21][C:20]3[C:33]([CH3:37])=[CH:34][CH:35]=[N:36][C:19]2=3)[CH2:17][CH2:16]1.O[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]=[CH:41][CH:40]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH:15]1([N:18]2[C:24]3[N:25]=[CH:26][C:27]([CH2:29][CH2:30][O:31][C:39]4[C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[N:42]=[CH:41][CH:40]=4)=[CH:28][C:23]=3[C:22](=[O:32])[NH:21][C:20]3[C:33]([CH3:37])=[CH:34][CH:35]=[N:36][C:19]2=3)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 18466641HCID 18466641, compoundHCID 178516385quinolin-4-ol

Product 1

HCID 3010647HCID 3010647, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (DIAD) (167 μL, 0.85 mmol) was added drop-wise to a solution of 11-(cyclopropyl)-5,11-dihydro-8-(2-hydroxyethyl)-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (175 mg, 0.57 mmol), 4-hydroxyquinoline (123 mg, 0.85 mmol) and Ph3P (223 mg, 0.85 mmol) in THF (2.8 mL) at room temperature. The mixture was stirred at room temperature for 3 h then was concentrated under reduced pressure. The residue was dissolved in EtOAc (60 mL) and the solution was successively washed with 3 N aqueous NaOH (3×20 mL), aqueous saturated NH4Cl (20 mL) and brine (20 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:MeOH; 95:5) to give the title compound (74 mg, 30% yield) as a white solid: MS (ESI) m/z 438 (MH)+.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (60 mL)
  3. washthe solution was successively washed with 3 N aqueous NaOH (3×20 mL), aqueous saturated NH4Cl (20 mL) and brine (20 mL)
  4. dry with materialthen was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (EtOAc:MeOH; 95:5)

Sources & evidence

ORD record
ord-376cba0db54e4278a5380c6e6486a880
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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