Triphenylphosphine → HCID 59406683, compound

HRID 383630Notes

Reaction equation

HRID 383630 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16](=[O:19])[NH:17][N:18]=3)=[CH:9][CH:8]=2)[N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:17]1[C:16](=[O:19])[CH:15]=[CH:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:12][CH:11]=2)=[N:18]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 802933-Aminobenzyl alcoholHCID 59406765HCID 59406765, compound

Product 1

HCID 59406683HCID 59406683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (10 mmol) of 6-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2H-pyridazin-3-one, 1.85 g (15 mmol) of 3-aminobenzyl alcohol and 3.9 g (15 mmol) of triphenylphosphine are suspended in 60 ml of THF under a nitrogen atmosphere, and the mixture is stirred at room temperature for 10 min. 2.9 g (15 mmol) of diisopropyl azodicarboxylate is then added dropwise over the course of 15 min. The reaction mixture is stirred at room temperature for 3 hours and subsequently evaporated. The residue is taken up in about 70 ml of 2-propanol, and the mixture is stirred for 15 minutes. The residue is filtered off with suction, washed well with 2-propanol, then with MTBE. The residue is dried in vacuo.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 3 hours
  2. customsubsequently evaporated
  3. stirringthe mixture is stirred for 15 minutes
  4. filtrationThe residue is filtered off with suction
  5. washwashed well with 2-propanol
  6. customThe residue is dried in vacuo

Sources & evidence

ORD record
ord-ddbff021131e416d9f1326c3ab1e1ed4
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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