Pyridine → HCID 178511144, compound

HRID 2423254Notes

Reaction equation

HRID 2423254 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:10]=[C:11]([C:16](=[O:43])[C:17](=[C:34]2[NH:38][C:37]3[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=3[NH:35]2)[C:18]([C:20]2[CH:21]=[C:22]([S:26]([NH:29]C(=N)CO)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1.[Cl-].[NH4+].[N:46]1C=CC=[CH:48][CH:47]=1>>[F:15][C:13]1[CH:12]=[C:11]([C:16](=[O:43])[C:17](=[C:34]2[NH:35][C:36]3[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=3[NH:38]2)[C:18]([C:20]2[CH:21]=[C:22]([S:26]([NH:29][CH:6]([CH2:48][CH:47]=[NH:46])[C:5]([OH:4])=[O:7])(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=2)=[O:19])[CH:10]=[C:9]([F:8])[CH:14]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 178511450HCID 178511450, compound

Product 1

HCID 178511144HCID 178511144, compound

Procedure

Acetic anhydride (90 mg) was added to a pyridine (5 mL) solution of N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)-2-hydroxyethanimidamide (225 mg), followed by stirring at room temperature for 2 hours. An excess amount of an aqueous saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=80/1) and crystallized from ethyl acetate/n-hexane to obtain 2-[({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)amino]-2-iminoethylacetic acid (150 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=80/1)
  5. customcrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-84cb9002aba942cea82dc0a3c080b295
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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