Water → HCID 21949897, compound

HRID 558292Notes

Reaction equation

HRID 558292 reaction equation
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([C:22]1[C:26]([O:27][C:28]2[CH:29]=[C:30]([C:36]#[N:37])[CH:31]=[C:32]([CH:35]=2)[C:33]#[N:34])=[C:25]([CH3:38])[N:24]([CH2:39][CH2:40]O)[N:23]=1)([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/[N:66]=N/C(OCC)=O)=O.O>O1CCCC1>[NH3:15].[NH2:66][CH2:40][CH2:39][N:24]1[C:25]([CH3:38])=[C:26]([O:27][C:28]2[CH:29]=[C:30]([C:36]#[N:37])[CH:31]=[C:32]([CH:35]=2)[C:33]#[N:34])[C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:23]1

Participants

8

Reactant 5

HCID 962WaterHCID 11776Triphenylphosphine2×HCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 21949857HCID 21949857, compound

Product 2

HCID 222AmmoniaHCID 21949897HCID 21949897, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diphenylphosphorylazide (305 mg, 1.10 mmol) was dissolved in tetrahydrofuran (5 ml) and added to a solution of the pyrazole from Example 157 (180 mg, 0.55 mmol), triphenylphosphine (291 mg, 1.10 mmol) and diethylazodicarboxylate (193 mg, 1.10 mmol) in tetrahydrofuran (20 ml) under nitrogen at room temperature. The reaction was stirred for 18 hours then triphenylphosphine (291 mg, 1.10 mmol) was added, and the reaction was stirred for a further 18 hours. Water (180 μl, 10.0 mmol) was then added and the reaction was stirred for 64 hours. The solvent was removed under reduced pressure and the residual white paste was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (95:4.5:0.5, by volume) to provide the title compound (55 mg) as a colourless oil.

Workup

  1. stirringthe reaction was stirred for a further 18 hours
  2. stirringthe reaction was stirred for 64 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residual white paste was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-36738ef68818463ba0f508013f0335ec
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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