Potassium Carbonate → [3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

HRID 1968667노트

반응식

HRID 1968667 반응식
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:41])([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:29][N:28]=3)[CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[N:13]=1)(=O)C.C(=O)(O)[O-].[Na+]>O.CO>[CH3:41][C:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:13]=[C:12]([CH2:11][OH:10])[O:16][N:15]=2)=[CH:18][CH:19]=1)([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:29][N:28]=1)[CH:24]([CH3:26])[CH3:25]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57910807[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methyl acetate

생성물 1

HCID 57910795[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Potassium carbonate (743 mg, 5.38 mmol) in water (1.00 mL) was added to a stirred solution of 3c (0.896 mmol) in MeOH (3.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent) to furnish the title compound 3d. m/z (ES) 431 (MH)+. 1HNMR. (500 MHz, CD3OD): δ 8.55 (d, 1H, J=3.3 Hz), 8.28 (d, 1H, J=2.7 Hz), 7.94 (d, 2H, J=8.5 Hz), 7.88 (dt, 1H, J=1.7, 7.7 Hz), 7.61 (d, 1H, J=7.8 Hz), 7.48 (d, 2H, J=8.5 Hz), 7.35 (m, 3H), 5.23 (s, 2H), 3.08 (m, 1H, J=6.6 Hz), 1.70 (s, 3H), 0.86 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.6 Hz).

후처리

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent)

출처 및 근거

ORD 기록
ord-1c89d9e766834314bbf9a011fc90a1cb
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426413B2

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