3-Phenylphenol → HCID 10068126, compound

HRID 1295690Notes

Reaction equation

HRID 1295690 reaction equation
CN(C(/N=N/C(N(C)C)=O)=O)C.C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32]CCO)=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.[C:36]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:37]=1.[C:55]1([C:61]2[CH:62]=[C:63]([OH:67])[CH:64]=[CH:65][CH:66]=2)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C1COCC1.CN(C=O)C>[C:61]1([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:66]=[CH:65][CH:64]=[C:63]([O:67][CH2:36][CH2:37][N:28]2[CH:29]=[CH:30][N:31]=[C:26]([N:23]3[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]3)[C:27]2=[O:32])[CH:62]=1

Participants

7

Reactant 4

HCID 113813-PhenylphenolHCID 11776TriphenylphosphineHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 10068126HCID 10068126, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

TMAD (0.060 g, 0.35 mmol) was dissolved in THF (1 mL) and DMF (0.5 mL) and the resulting solution was added dropwise to a mixture of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.100 g, 0.31 mmol), triphenylphosphine (0.092 g, 0.35 mmol) and 3-phenylphenol (0.170 g, 1.00 mmol) in THF (0.5 mL). The reaction mixture was stirred overnight at room temperature, concentrated, and put through a silica column using toluene/EtOAc (7:3) as eluent. Solvents were removed in vacuo and the resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min with stirring. The mixture was concentrated and the residue purified by chromatography on silica gel using EtOAc/HOAc/MeOH/H2O (20:3:3:2) as eluent. The product-containing fractions were concentrated, washed between dichloromethane/5% aqueous NaOH, and put through a silica column using dichloromethane/MeOH (8:2) as eluent to give 16 mg (16%) of the title compound. HRMS m/z calcd for C22H24N4O2 (M)+ 376.1899, found 376.1888.

Workup

  1. concentrationconcentrated
  2. customSolvents were removed in vacuo
  3. additionthe resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min
  4. stirringwith stirring
  5. concentrationThe mixture was concentrated
  6. customthe residue purified by chromatography on silica gel
  7. concentrationThe product-containing fractions were concentrated
  8. washwashed between dichloromethane/5% aqueous NaOH

Sources & evidence

ORD record
ord-69d78effa63b490f8500300967e73c80
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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