Triphenylphosphine → HCID 10339254, 화합물

HRID 1295689

반응식

HRID 1295689 반응식
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.[CH2:55]([O:59][C:60]1[CH:61]=[C:62]([OH:66])[CH:63]=[CH:64][CH:65]=1)[CH2:56][CH2:57][CH3:58]>C1COCC1.CN(C=O)C>[CH2:55]([O:59][C:60]1[CH:61]=[C:62]([CH:63]=[CH:64][CH:65]=1)[O:66][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])[CH2:56][CH2:57][CH3:58]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 878763-ButoxyphenolHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

생성물 1

HCID 10339254HCID 10339254, 화합물수율 84%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

TMAD (0.060 g, 0.35 mmol) was dissolved in THF (1 mL) and DMF (0.5 mL) and the solution was added dropwise to a mixture of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.100 g, 0.310 mmol), triphenylphosphine (0.092 g, 0.35 mmol) and 3-n-butyloxyphenol (0.166 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 97 mg (7%) of the title compound. HRMS m/z calcd for C20H28N4O3 (M)+ 372.2161, found 372.2149.

후처리

  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

출처 및 근거

ORD 기록
ord-294df39cd87b47d598ccc0465638a92c
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244722B2

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