Water → 1-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

HRID 499796노트

반응식

HRID 499796 반응식
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]3=[O:20])=[CH:10][CH:9]=2)[CH:7]=1.O=S(Cl)Cl.[N-:25]=[N+:26]=[N-:27].[Na+].O>CC#N.CCOC(C)=O>[N:25]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]3=[O:20])=[CH:10][CH:9]=2)[CH:7]=1)=[N+:26]=[N-:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 669743311-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

생성물 1

HCID 866163341-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 1-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one prepared above (335 mg, 1.25 mmol) in CH3CN (20 mL), SOCl2 (5.0 mL) was added. After the mixture was stirred at room temperature for 2 h, it was concentrated in vacuo. The residue was then dissolved in DMF (20 mL). To the solution, NaN3 (244 mg, 3.75 mmol) was added. After the mixture was stirred at room temperature overnight, water and EtOAc were added. The organic layer was separated, washed with 5% aq. NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one (203 mg). MS 293 (M+H).

후처리

  1. concentrationit was concentrated in vacuo
  2. dissolutionThe residue was then dissolved in DMF (20 mL)
  3. stirringAfter the mixture was stirred at room temperature overnight
  4. customThe organic layer was separated
  5. washwashed with 5% aq. NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1e1a22bb6cea43ffa0ad6117fbf96d1b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767697B2

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