Trifluoroacetic acid → HCID 10344134, compound

HRID 1983805Notes

Reaction equation

HRID 1983805 reaction equation
C(O[C:6]([N:8]([CH3:30])[C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[C:15]([N:17]([CH:19]([CH3:21])[CH3:20])[CH3:18])[N:14](C(OC(C)(C)C)=O)[C:13]=2[CH:29]=1)=[O:7])(C)(C)C.[OH-:31].[Na+].C[CH2:34][N:35]=[C:36]=[N:37]CCCN(C)C.Cl.[CH:45]1[CH:46]=[CH:47][C:48]2N(O)N=N[C:49]=2[CH:50]=1.C(=O)([O-])O.[Na+].[F:60][C:61]([F:66])([F:65])C(O)=O>CN(C)C=O.O>[CH:19]([N:17]([CH3:18])[C:15]1[NH:14][C:13]2[CH:29]=[C:9]([N:8]([CH3:30])[C:6]([C:36]3[N:35]=[C:34]([C:49]4[CH:48]=[CH:47][C:46]([C:61]([F:66])([F:65])[F:60])=[CH:45][CH:50]=4)[O:31][N:37]=3)=[O:7])[CH:10]=[CH:11][C:12]=2[N:16]=1)([CH3:20])[CH3:21]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68807874HCID 68807874, compound

Product 1

HCID 10344134HCID 10344134, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Thus obtained mixture (207 mg) of tert-butyl 5-[(t-butoxycarbonyl)(methyl)amino]-2-[isopropyl(methyl)amino-1H-benzimidazole-1-carboxylate and tert-butyl 6-[(t-butoxycarbonyl)(methyl)amino]-2-[isopropyl(methyl)amino]-1H-benzimidazole-1-carboxylate was dissolved in trifluoroacetic acid (2 ml) and stirred for 3.5 hours. 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 to provide an oily substance (117 mg). Thus obtained amine-form (61 mg) was dissolved in dimethylformamide (2.5 ml), and to the solution carboxylic acid (61 mg), WSC.HCl (67 mg), HOBt.monohydrate (47 mg) and sodium hydrogencarbonate (79 mg) were added, followed by stirring at room temperature for 15 hours. Water was added and the system was extracted with ethyl acetate. 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 (34 mg).

Workup

  1. customThe reaction liquid
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto provide an oily substance (117 mg)
  6. stirringby stirring at room temperature for 15 hours
  7. extractionthe system was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customcondensed under reduced pressure
  11. custompurified on preparative TLC (methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-740a8a1f182041e4a0a1462f02bede6d
Source dataset
uspto-grants-2009_06
Patent number
US07541477B2

Reaction notes

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