Hydrochloric Acid → HCID 67237942, compound

HRID 1521754Notes

Reaction equation

HRID 1521754 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[C:16](C(OC)(OC)OC)[N:15]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])OC(C)(C)C)[C:14]=3[CH:36]=2)=[O:9])[CH:2]=1.Cl.C(N(CC)CC)C>CO.C(Cl)Cl>[O:35]=[C:29]1[C:16]2=[N:17][C:13]3[CH:12]=[CH:11][C:10]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:9])=[CH:36][C:14]=3[N:15]2[CH2:25][CH2:26][CH2:27][NH:28]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 68322710HCID 68322710, compound

Product 1

HCID 67237942HCID 67237942, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {3-[6-(pyridin-3-ylcarbamoyl)-2-(trimethoxymethyl)-1H-benzimidazol-1-yl]propyl}carbamate (85 mg, 0.17 mmol) in methanol (2 mL) was added concentrated HCl (1 mL). The solution is stirred at room temperature for 2 h and is evaporated to dryness. The residue is dissolved in methanol (5 mL), triethylamine (0.14 mL, 1.0 mmol) added, and the solution heated at reflux for 2 h. The cooled solution was diluted with CH2Cl2, and washed with Na2CO3. The organic layer was dried (MgSO4) and evaporated. The crude product was purified via preparative HPLC. The major peak was collected by passing the HPLC fractions, without concentrating, directly through an SCX cartridge (Silicycle tosic acid, 1 g). The cartridge was washed with methanol, then CH2Cl2/methanol (50:50). Finally, the product was eluted with CH2Cl2/methanol containing 1% NH4OH. The solution containing product was evaporated to afford the title compound (13 mg, 22%).

Workup

  1. customis evaporated to dryness
  2. dissolutionThe residue is dissolved in methanol (5 mL)
  3. temperaturethe solution heated
  4. temperatureat reflux for 2 h
  5. washwashed with Na2CO3
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified via preparative HPLC
  9. customThe major peak was collected
  10. concentrationwithout concentrating, directly through an SCX cartridge (Silicycle tosic acid, 1 g)
  11. washThe cartridge was washed with methanol
  12. washFinally, the product was eluted with CH2Cl2/methanol containing 1% NH4OH
  13. additionThe solution containing product
  14. customwas evaporated

Sources & evidence

ORD record
ord-ad47bab3dcd1474bba7851c181a5435f
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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