N,N,N',N'-Tetramethylazodicarboxamide → 2-[3-(4-Morpholinyl)phenoxy]ethyl 3-(1-piperazinyl)-2-pyrazinyl ether

HRID 493289노트

반응식

HRID 493289 반응식
N(C(N(C)C)=O)=NC(N(C)C)=O.C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32][CH2:33][CH2:34][OH:35])=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.[N:36]1([C:42]2[CH:43]=[C:44](O)[CH:45]=[CH:46][CH:47]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:23]1([C:26]2[C:27]([O:32][CH2:33][CH2:34][O:35][C:46]3[CH:45]=[CH:44][CH:43]=[C:42]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)[CH:47]=3)=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]1

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 11776TriphenylphosphineHCID 1413433-MorpholinophenolHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

생성물 1

HCID 220362362-[3-(4-Morpholinyl)phenoxy]ethyl 3-(1-piperazinyl)-2-pyrazinyl ether수율 10.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1,1′-Azobis(N,N-dimethylformamide) (TMAD; 256 mg, 1.50 mmol) was added to a solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (400 mg. 1.24 mmol; prepared in Example 52, Step 2), 3-(4-morpholinyl)phenol (441 mg, 1 23 mmol) and triphenylphosphine (646 mg, 2.46 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature for 2.5 h and then concentrated. The residue was purified by repeated chromatography on silica gel using toluene and toluene/EtOAc (8.2) as eluents Solvents were evaporated and the residue was treated with CH2Cl2/TFA/H2O (1:0.9:0. 1; 5 mL) at room temperature for 0.5 h. After concentration. 5 M NaOH was added followed by extraction with CH2Cl2. The organic phase was dried (K2CO3), filtered, and concentrated The residue was purified by chromatography on silica gel using CHCl3/MeOH (9 1) as eluent to give 50 mg (10%) of the title product as on oil. HRMS m/z calcd for C20H27N5O3 (M)+ 385.2114, found 385 2100.

후처리

  1. concentrationconcentrated
  2. customThe residue was purified
  3. customwere evaporated
  4. additionthe residue was treated with CH2Cl2/TFA/H2O (1:0.9:0. 1; 5 mL) at room temperature for 0.5 h
  5. concentrationAfter concentration
  6. addition5 M NaOH was added
  7. extractionfollowed by extraction with CH2Cl2
  8. dry with materialThe organic phase was dried (K2CO3)
  9. filtrationfiltered
  10. concentrationconcentrated The residue
  11. customwas purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-59dba8887de44d9a9df8053040adde7f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534794B2

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