HCID 22914863, compound → HCID 22914883, compound

HRID 1377521Notes

Reaction equation

HRID 1377521 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH:33]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])[N:36]=2)[OH:34])=[C:7]([Cl:47])[N:6]=1)[CH2:2][CH2:3][CH3:4]>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])[N:36]=2)=[O:34])=[C:7]([Cl:47])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 22914863HCID 22914863, compound

Product 1

HCID 22914883HCID 22914883, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50 mg (0.076 mmole) of the compound obtained in step 1 of Example 12 was dissolved in 3 ml of methylene chloride and to the resulting solution was added 64.5 mg (0.152 mmole) of Des-Martin reagent. The resultant was stirred for 2 hours at room temperature and 10 ml of methylene chloride was added additionally thereto. The reaction mixture was washed with 5 ml of aqueous sodium bicarbonate solution, dried over anhydrous Na2SO4, concentrated under reduced pressure and purified with silica gel column chromatography to obtain 43.7 mg of the title compound (yield 87.8%).

Workup

  1. additionwas added 64.5 mg (0.152 mmole) of Des-Martin reagent
  2. washThe reaction mixture was washed with 5 ml of aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-627ec5d21be44e9394580ef224d5c8ef
Source dataset
uspto-grants-1997_09
Patent number
US05665738

Reaction notes

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