Triphenylphosphine → HCID 3010649, compound

HRID 2229328Notes

Reaction equation

HRID 2229328 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]([CH3:38])=[CH:34][C:35]([F:37])=[N:36][C:19]2=3)[CH2:17][CH2:16]1.O[C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]=[CH:42][CH:41]=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:40]4[C:49]5[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=5)[N:43]=[CH:42][CH:41]=4)=[CH:28][C:23]=3[C:22](=[O:32])[NH:21][C:20]3[C:33]([CH3:38])=[CH:34][C:35]([F:37])=[N:36][C:19]2=3)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 18466640HCID 18466640, compoundHCID 178516385quinolin-4-ol

Product 1

HCID 3010649HCID 3010649, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (DIAD) (131 μL, 0.66 mmol) was added drop-wise to a solution of 11-(cyclopropyl)-5,11-dihydro-2-fluoro-8-(2-hydroxyethyl)-4methyl-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (140 mg, 0.44 mmol), 4-hydroxyquinoline (96.4 mg, 0.66 mmol) and Ph3P (124 mg, 0.66 mmol) in THF (2.2 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 partially purified by flash chromatography (EtOAc:MeOH; 95:5). The solid was further purified by reverse phase HPLC (CombiPrep ADS-AQ 50×20 mm, 5 μ120 A, 5-100% MeCN+0.10% TFA/water+0.10% TFA in 25 min) to give the bifluoroacetic acid salt of the title compound (104 mg, 43% yield) as a white solid: MS (ESI) m/z 456 (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 partially purified by flash chromatography (EtOAc:MeOH; 95:5)
  8. customThe solid was further purified by reverse phase HPLC (CombiPrep ADS-AQ 50×20 mm, 5 μ120 A, 5-100% MeCN+0.10% TFA/water+0.10% TFA in 25 min)

Sources & evidence

ORD record
ord-2aca20a098ac4366a3ae2e2cc42e919f
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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