Water → HCID 57767004, compound

HRID 1670713Notes

Reaction equation

HRID 1670713 reaction equation
N1C=NN=N1.C(N(CC)[P:9]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])C.[OH:22][C:23]1[CH:24]=[CH:25][C:26]2[N:48]([CH:49]=1)[C:29]1[N:30]([C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)[C:31](=[O:38])[C:32]3[C:37]([C:28]=1[N:27]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3.C([O:54]O)(C)(C)C.O>C(#N)C>[N+:45]([C:42]1[CH:43]=[CH:44][C:39]([N:30]2[C:29]3[N:48]4[CH:49]=[C:23]([O:22][P:9](=[O:54])([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:24]=[CH:25][C:26]4=[N:27][C:28]=3[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:38])=[CH:40][CH:41]=1)([O-:47])=[O:46]

Participants

7

Reactant 5

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 24771030HCID 24771030, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 57767004HCID 57767004, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tetrazole (2.0 equiv., 5.37 mmol, 0.38 g) and di-(tert-butyl) diethylphosphoramidite (1.6 equiv., 4.30 mmol, 1.07 g) were added to a solution of 10 (1.0 equiv., 2.69 mmol, 1.00 g) in anhydrous acetonitrile under Ar atmosphere. The reaction mixture was stirred at room temperature for 1 h. A 70% tert-butyl hydroperoxide solution in water (5.0 equiv., 13.45 mmol, 1.73 g) was added slowly and stirring was continued for 1 h. The reaction mixture was filtered through a glass filter and the filtrate was evaporated under reduced pressure. Purification by column chromatography (dichloromethane/methanol 97.2:2.5) afforded phosphoric acid di-tert-butyl ester 6-(4-nitrophenyl)-5-oxo-5,6-dihydro-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl ester (I21). A suspension of I21 in a 4 M HCl solution in isopropanol was stirred at room temperature overnight. The solvent was removed under reduced pressure to give phosphoric acid 5,6-dihydro-6-(4-nitrophenyl)-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl ester (76) as a hydrochloride salt (0.47 g, yield=36%, purity (LC)>95%).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. filtrationThe reaction mixture was filtered through a glass
  4. filtrationfilter
  5. customthe filtrate was evaporated under reduced pressure
  6. customPurification by column chromatography (dichloromethane/methanol 97.2:2.5)

Sources & evidence

ORD record
ord-a5724ee6909a43279c8ccdde53333aad
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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