Triphenylphosphine → 3-(1-Benzoyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 1097784노트

반응식

HRID 1097784 반응식
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]([C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:41])[CH2:32][CH2:31]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:9][O:8][C:6]([C:4]1[N:3]([CH:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([C:40](=[O:41])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:32][CH2:31]2)[CH:2]=[N:1][CH:5]=1)=[O:7]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59277722N-benzoyl-1,2,3,4-tetrahydroquinolin-4-olHCID 178418785HCID 178418785, 화합물

생성물 1

HCID 592777153-(1-Benzoyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

methyl 4-imidazolecarboxylate (200 mg, 1.59 mmol) and PS-triphenylphosphine (2.15 mmol/g, 0.90 g, 1.94 mmol) are added to a solution of (4-hydroxy-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (380 mg, 1.50 mmol) in THF (20 mL) at room temperature. The resulting mixture is stirred at room temperature for 5 minutes and then cooled to 0° C. DIAD (0.38 mL, 1.96 mmol) is added, and the mixture is slowly warmed up to room temperature. After 3 h, the reaction mixture is filtered to remove resin and washed with ethyl acetate. The combined ethyl acetate solution is washed with brine, and dried with anhydrous sodium sulfate. After concentration, the residue is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins) to give the title compound: 1H NMR (400 MHz, CDCl3) δ ppm 2.21-2.30 (m, 1 H), 2.52-2.62 (m, 1 H), 3.75-3.82 (m, 1 H), 3.89 (s, 3 H), 4.11-4.18 (m, 1 H), 6.40 (t, J=6.1 Hz, 1 H), 6.94 (d, J=7.6 Hz, 1 H), 7.01-7.09 (m, 3 H), 7.33-7.40 (m, 3 H), 7.40-7.45 (m, 1 H), 7.46-7.50 (m, 2 H), 7.85 (d, J=0.8 Hz, 1 H).

후처리

  1. temperaturecooled to 0° C
  2. temperaturethe mixture is slowly warmed up to room temperature
  3. waitAfter 3 h
  4. filtrationthe reaction mixture is filtered
  5. customto remove resin
  6. washwashed with ethyl acetate
  7. washThe combined ethyl acetate solution is washed with brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationAfter concentration
  10. customthe residue is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins)

출처 및 근거

ORD 기록
ord-1df04698d67147ad92a6fefc24c60844
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143278B2

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