Triphenylphosphine → 3-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl)oxymethyloxazolidin-2-one

HRID 1167484Notes

Reaction equation

HRID 1167484 reaction equation
[C:1]([C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]4=[O:28])=[CH:17][C:16]=3[F:29])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O[C:31]1[CH:35]=[CH:34][O:33][N:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[C:1]([C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][C@H:24]([CH2:26][O:27][C:31]5[CH:35]=[CH:34][O:33][N:32]=5)[O:23][C:22]4=[O:28])=[CH:17][C:16]=3[F:29])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 213566023-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 699799723-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl)oxymethyloxazolidin-2-oneYield 25.8%

Procedure

3-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-one (398 mg, 1 mmol), 3-hydroxyisoxazole (93.5 mg, 1.1 mmol) and triphenylphosphine (328 mg, 1.25 mmol), were suspended with stirring in dry tetrahydrofiran (10 ml). Diisopropylazodicarboxylate (242 mg, 1.2 mmol) was added dropwise by syringe, and the mixture stirred at ambient temperature for 30 minutes. The reaction mixture was filtered, evaporated to dryness, dissolved in EtOAc/isohexane (1:1), and applied to a 10 g silica Mega Bond Elut® column, eluting with a gradient from 75 to 100% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the title compound (120 mg).

Workup

  1. stirringthe mixture stirred at ambient temperature for 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. dissolutiondissolved in EtOAc/isohexane (1:1)
  5. washeluting with a gradient from 75 to 100% EtOAc in isohexane
  6. customevaporated

Sources & evidence

ORD record
ord-4ab8488b229d4b51af22bd24167211a5
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

Loading…