Triphenylphosphine → HCID 178430630, compound

HRID 49269Notes

Reaction equation

HRID 49269 reaction equation
[CH3:1][CH:2](O)[CH2:3][NH:4][C:5]([NH:13][C:14]#[N:15])=[N:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.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>[CH3:1][CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:5](=[N:13][C:14]#[N:15])[NH:4][CH2:3]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178468273HCID 178468273, compound

Product 1

HCID 178430630HCID 178430630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of N-(2-methyl-2-hydroxyethyl)-N′-cyano-N″-4-pyridylguanidine (0.5 g, 2.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in THF (20 mL) at 0° C. under nitrogen was added diisopropyl azodicarboxylate (0.92 g, 4.5 mmol) dissolved in THF (10 mL) dropwise over 15 minutes. The resulting mixture was stirred at 0° C. for another 2 hours and then warmed to room temperature for 60 hours. After the reaction was complete, the mixture was concentrated and purified by chromatography on silica gel using ethyl acetate as eluant to remove triphenylphosphine and triphenylphosphine oxide followed by clution with a mixture of dichloromethane and methanol (7:1) to afford the product (i.e., Compound 12) as a white solid (0.23 g, 50%).

Workup

  1. temperaturewarmed to room temperature for 60 hours
  2. concentrationthe mixture was concentrated
  3. custompurified by chromatography on silica gel
  4. customto remove triphenylphosphine and triphenylphosphine oxide
  5. additionfollowed by clution with a mixture of dichloromethane and methanol (7:1)

Sources & evidence

ORD record
ord-7e6f991e49584ca09d2e5d675c7770b3
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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