Sodium Hydroxide → HCID 23080309, compound

HRID 1983804Notes

Reaction equation

HRID 1983804 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([O:20]C3C=CC=CC=3)=O)=[CH:16][C:11]=2[N:10]=[C:9]1[N:27]([CH:29]([CH3:31])[CH3:30])[CH3:28])=O)(C)(C)C.C(N(C)C1N(C(OC(C)(C)C)=O)C2C=C(NC(OC3C=CC=CC=3)=O)C=CC=2N=1)(C)C.Cl.[F:64][C:65]1[CH:70]=[CH:69][C:68]([CH:71]2[CH2:76][CH2:75][NH:74][CH2:73][CH2:72]2)=[CH:67][CH:66]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[F:64][C:65]1[CH:70]=[CH:69][C:68]([CH:71]2[CH2:72][CH2:73][N:74]([C:18]([NH:17][C:15]3[CH:14]=[CH:13][C:12]4[N:8]=[C:9]([N:27]([CH:29]([CH3:30])[CH3:31])[CH3:28])[NH:10][C:11]=4[CH:16]=3)=[O:20])[CH2:75][CH2:76]2)=[CH:67][CH:66]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochlorideHCID 68807141HCID 68807141, compoundHCID 68807343HCID 68807343, compound

Product 1

HCID 23080309HCID 23080309, compoundYield 7.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of said mixture (157 mg of tert-butyl-2-[isopropyl(methyl)amino]-5-[(phenoxycarbonyl)amino]-1H-benzimidazole-1-carboxylate and tert-butyl 2-[isopropyl(methyl) amino]-6-[(phenoxycarbonyl)amino]-1H-benzimidazole-1-carboxylate in chloroform (3 ml), 4-(4-fluorophenyl)piperidine hydrochloride (76 mg) and triethylamine (0.16 ml) were added and heated at 60° C. for 1.5 hours. The reaction liquid was cooled and after addition of water, extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure and the resulting residue was purified on preparative TLC (hexane/ethyl acetate=1/9). Thus obtained compound was dissolved in trifluoroacetic acid (2 ml) and stirred for an hour. The reaction liquid was made alkaline by addition of 4N-aqueous NaOH solution and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure and purified on preparative TLC (methanol/chloroform=1/9) to provide the title compound (11 mg).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe resulting residue was purified on preparative TLC (hexane/ethyl acetate=1/9)
  8. dissolutionThus obtained compound was dissolved in trifluoroacetic acid (2 ml)
  9. customThe reaction liquid
  10. extractionextracted with chloroform
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customcondensed under reduced pressure
  14. custompurified on preparative TLC (methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-ea8904d195ef42759d7e46f09ac0a5e2
Source dataset
uspto-grants-2009_06
Patent number
US07541477B2

Reaction notes

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