Dichloromethane → HCID 178468368, compound

HRID 2423251Notes

Reaction equation

HRID 2423251 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl.[F:26][C:27]1[CH:28]=[C:29]([C:34](=[O:62])[C:35](=[C:53]2[NH:57][C:56]3[CH:58]=[CH:59][CH:60]=[CH:61][C:55]=3[NH:54]2)[C:36]([C:38]2[CH:39]=[C:40]([S:44]([NH:47][C:48](=[NH:52])[CH:49]([OH:51])[CH3:50])(=[O:46])=[O:45])[CH:41]=[CH:42][CH:43]=2)=[O:37])[CH:30]=[C:31]([F:33])[CH:32]=1>C(OCC)(=O)C>[F:26][C:27]1[CH:28]=[C:29]([C:34](=[O:62])[C:35](=[C:53]2[NH:54][C:55]3[CH:61]=[CH:60][CH:59]=[CH:58][C:56]=3[NH:57]2)[C:36]([C:38]2[CH:39]=[C:40]([S:44]([NH:47][C:48](=[NH:52])[C:49](=[O:51])[CH3:50])(=[O:45])=[O:46])[CH:41]=[CH:42][CH:43]=2)=[O:37])[CH:30]=[C:31]([F:33])[CH:32]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 178468369HCID 178468369, compound

Product 1

HCID 178468368HCID 178468368, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin reagent (15 wt. % dichloromethane solution, 0.73 mL) was added to a dichloromethane (2 mL) solution of N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)-2-hydroxypropanimidamide (90 mg), followed by stirring at room temperature for 4 hours. Ethyl acetate was added to the reaction mixture, washed with water, dried over anhydrous magnesium sulfate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1), and recrystallized from ethyl acetate/n-hexane to obtain N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)-2-oxopropanimidamide (57 mg).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)
  5. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-7a2b149938f546f28412fdd502a68a4f
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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