Toluene → 2-(4-Tert-butylsulfonylaminopiperidin-1-yl)-5-phenylbenzimidazole

HRID 639436Notes

Reaction equation

HRID 639436 reaction equation
C1(C)C=CC=CC=1.[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][S:17]([C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH2:12][CH2:11]1)#[N:9].[C:24]1([C:30]2[CH:35]=[CH:34][C:33](N)=[C:32]([NH2:37])[CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(OCC)(=O)C>[C:20]([S:17]([NH:16][CH:13]1[CH2:12][CH2:11][N:10]([C:8]2[NH:37][C:32]3[CH:31]=[C:30]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:35]=[CH:34][C:33]=3[N:9]=2)[CH2:15][CH2:14]1)(=[O:19])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 1140TolueneHCID 2733225Ytterbium triflateHCID 6452000(1,1'-Biphenyl)-3,4-diamineHCID 231541731-Cyano-4-(tert-butylsulfonylamino)piperidine

Product 1

HCID 113733002-(4-Tert-butylsulfonylaminopiperidin-1-yl)-5-phenylbenzimidazoleYield 32.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To the toluene solution (1 mL) containing 1-cyano-4-(tert-butylsulfonylamino)piperidine (22 mg) were added 4-phenyl-1,2-phenylenediamine (20 mg) and ytterbium triflate (20 mg), and the mixture was stirred in a sealed tube at 130° C. for 16 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and aqueous saturated sodium chloride solutions successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was separated and purified on a collective thin-layer chromatograph (chloroform:methanol=15:1) to give the title compound (12 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and aqueous saturated sodium chloride solutions successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified on a collective thin-layer chromatograph (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-e65b0e739276460987c597aa6107c15b
Source dataset
uspto-grants-2010_04
Patent number
US07691860B2

Reaction notes

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