3-(Trifluoromethyl)phenol → HCID 10339004, compound

HRID 1295695Notes

Reaction equation

HRID 1295695 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.[OH:55][C:56]1[CH:57]=[C:58]([C:62]([F:65])([F:64])[F:63])[CH:59]=[CH:60][CH:61]=1>C1COCC1>[N:23]1([C:26]2[C:27](=[O:32])[N:28]([CH2:36][CH2:37][O:55][C:56]3[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:63])([F:64])[F:65])[CH:57]=3)[CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 11776TriphenylphosphineHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 10339004HCID 10339004, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(TMAD; 129 mg, 0.75 mmol) was added to a mixture of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (200 mg, 0.62 mmol), triphenylphosphine (323 mg, 1.23 mmol), 3-hydroxybenzotrifluoride (199 mg, 1.23 mmol) in THF (1.5 mL). After being stirred at room temperature for 1 h, the reaction mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel using toluene/EtOAc (7:3) as eluent. The product-containing fractions were concentrated and the resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5) for 30 min with stirring. The mixture was concentrated in a speed vac overnight and the residue purified by chromatography on silica gel using CHCl3/MeOH (9:1) as eluent to afford 109 mg (49%) of the title compound. HRMS m/z calcd for C17H19F3N4O2 (M)+ 368.1460, found 368.1465.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica gel
  3. concentrationThe product-containing fractions were concentrated
  4. additionthe resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5) for 30 min
  5. stirringwith stirring
  6. concentrationThe mixture was concentrated in a speed vac overnight
  7. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-70504e8a4cbe4afca8ea7211594d64c5
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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