Triphenylphosphine → HCID 86686565, compound

HRID 1528084Notes

Reaction equation

HRID 1528084 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-])=O.[CH:9]1([CH:12]([CH:14]2[CH2:16][CH2:15]2)O)[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.O>[CH:9]1([CH:12]([CH:14]2[CH2:16][CH2:15]2)[N:6]2[CH:5]=[C:4]([NH2:1])[CH:8]=[N:7]2)[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 84336DicyclopropylmethanolHCID 66880968DIAD toluene

Product 1

HCID 86686565HCID 86686565, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole (500 mg), dicyclopropylmethanol (0.92 g) and triphenylphosphine (2.3 g) in THF (10 mL) was added diisopropyl azodicarboxylate toluene (1.9M, 4.6 mL) solution at room temperature. The reaction mixture was stirred at room temperature for 2 hr, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A suspension of the obtained residue and palladium on carbon (1 g) in methanol (30 mL) was stirred at room temperature for 12 hr under a hydrogen atmosphere, filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (140 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionA suspension of the obtained residue and palladium on carbon (1 g) in methanol (30 mL)
  5. stirringwas stirred at room temperature for 12 hr under a hydrogen atmosphere
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-54b41e3b59524d6786f01fef0bdae612
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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