Triphenylphosphine → HCID 10065573, compound

HRID 1295694Notes

Reaction equation

HRID 1295694 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.[F:55][C:56]1[CH:61]=[C:60]([F:62])[CH:59]=[CH:58][C:57]=1[OH:63]>C1COCC1>[F:55][C:56]1[CH:61]=[C:60]([F:62])[CH:59]=[CH:58][C:57]=1[O:63][CH2:36][CH2:37][N:28]1[CH:29]=[CH:30][N:31]=[C:26]([N:23]2[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]2)[C:27]1=[O:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1230512,4-DifluorophenolHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 10065573HCID 10065573, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TMAD (0.129 g, 0.750 mmol) was added to a solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.200 g, 0.620 mmol), triphenylphosphine (0.196 g, 1.23 mmol) and 2,4-difluorophenol (0.160 g, 1.23 mmol) in THF (1 mL) at room temperature. After being stirred for 2 h, the mixture was 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 30 mg (14%) of the title compound. HRMS m/z calcd for C16H18F2N4O2 (M)+ 336.1398, found 336.1392.

Workup

  1. concentrationthe mixture was concentrated
  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-b197c10cc44342098237da544298456d
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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