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

HRID 499796ノート

反応式

HRID 499796 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e1a22bb6cea43ffa0ad6117fbf96d1b
出典データセット
uspto-grants-2010_08
特許番号
US07767697B2

反応ノート

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