HCID 178513455, compound → HCID 178513454, compound

HRID 2423250Notes

Reaction equation

HRID 2423250 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:50])[C:10](=[C:41]2[NH:45][C:44]3[CH:46]=[CH:47][CH:48]=[CH:49][C:43]=3[NH:42]2)[C:11]([C:13]2[CH:14]=[C:15]([S:19]([NH:22][C:23](=[NH:40])[N:24]3[CH2:29][CH2:28][N:27](C(OCC4C=CC=CC=4)=O)[CH2:26][CH2:25]3)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:50])[C:10](=[C:41]2[NH:42][C:43]3[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=3[NH:45]2)[C:11]([C:13]2[CH:14]=[C:15]([S:19]([NH:22][C:23]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[NH:40])(=[O:20])=[O:21])[CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 178513455HCID 178513455, compound

Product 1

HCID 178513454HCID 178513454, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd—C (210 mg) was added to an ethanol (20 mL) solution of the compound (205 mg) obtained in Example 10, followed by stirring at room temperature for 19 hours under hydrogen atmosphere (1 atom). The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1), 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)piperazine-1-carboximidamide (46 mg).

Workup

  1. customThe insoluble matter was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)
  4. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e58bfe62e7274f44aebf40affb56f14b
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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