Sodium hydride → HCID 58928658, compound

HRID 853695Notes

Reaction equation

HRID 853695 reaction equation
[H-].[Na+].CO[C:5]([C:7]1[C:16]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[C:9]([O:31][CH3:32])[C:8]=1[CH2:33][C:34](=[O:44])[NH:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:6]>CN(C=O)C.C(OCC)C>[CH:18]([O:17][C:16]1[C:7]2[C:5](=[O:6])[N:35]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[C:34](=[O:44])[CH2:33][C:8]=2[C:9]([O:31][CH3:32])=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 58929022HCID 58929022, compound

Product 1

HCID 58928658HCID 58928658, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A 60% sodium hydride (NaH) mineral oil dispersion (0.002 g, 0.06 mmol was added to a solution of 8-benzhydryloxy-6-[(4-fluoro-benzylcarbamoyl)-methyl]-5-methoxy-quinoline-7-carboxylic acid methyl ester (0.020 g, 0.04 mmol) in 1 mL of anhydrous DMF. The resulting indigo-tinted solution was stirred at rt for a period of 30 min, and then diluted with diethyl ether (50 ml) and washed with sat. aq. NH4Cl (25 mL). The organic layer was dried over Na2SO4 and solvent was removed by rotary evaporation. The residue was purified by silica gel chromatography (1/1 hexanes/diethyl ether and then 100% MeOH to elute product fractions) to give 9-benzhydryloxy-7-(4-fluoro-benzyl)-10-methoxy-5H-1,7-diaza-anthracene-6,8-dione 295 (9 mg, 48%).

Workup

  1. washwashed with sat. aq. NH4Cl (25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4 and solvent
  3. customwas removed by rotary evaporation
  4. customThe residue was purified by silica gel chromatography (1/1 hexanes/diethyl ether
  5. wash100% MeOH to elute product fractions)

Sources & evidence

ORD record
ord-c27cc988164b4be7825042cff8fa2c83
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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