Acetonitrile → HCID 178513455, compound

HRID 2423249Notes

Reaction equation

HRID 2423249 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(#N)C.[F:20][C:21]1[CH:22]=[C:23]([C:28](=[O:60])[C:29](=[C:51]2[NH:55][C:54]3[CH:56]=[CH:57][CH:58]=[CH:59][C:53]=3[NH:52]2)[C:30]([C:32]2[CH:33]=[C:34]([S:38]([NH:41][C:42](N3C(C)=CC(C)=N3)=[NH:43])(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=2)=[O:31])[CH:24]=[C:25]([F:27])[CH:26]=1>C(OCC)(=O)C>[F:27][C:25]1[CH:24]=[C:23]([C:28](=[O:60])[C:29](=[C:51]2[NH:52][C:53]3[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=3[NH:55]2)[C:30]([C:32]2[CH:33]=[C:34]([S:38]([NH:41][C:42](=[NH:43])[N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[O:8])[CH2:2][CH2:3]3)(=[O:39])=[O:40])[CH:35]=[CH:36][CH:37]=2)=[O:31])[CH:22]=[C:21]([F:20])[CH:26]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 643495Benzyl piperazine-1-carboxylateHCID 178426540HCID 178426540, compound

Product 1

HCID 178513455HCID 178513455, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., benzyl piperazine-1-carboxylate (1.37 g) was added to an acetonitrile (5 mL) solution of N-({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)-3,5-dimethyl-1H-pyrazole-1-carboximidamide (205 mg), and heated under reflux for 3 days. After cooling, ethyl acetate was added, then washed with aqueous saturated ammonium chloride solution, water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/4) to obtain benzyl 4-[[({3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}sulfonyl)amino](imino)methyl]piperazine-1-carboxylate (76 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 days
  3. temperatureAfter cooling
  4. washwashed with aqueous saturated ammonium chloride solution, water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-98a7a1a4627e4769b399f53e2f28fe93
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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