Methanol → HCID 14153046, compound

HRID 1639135Notes

Reaction equation

HRID 1639135 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.[CH3:16][OH:17].[H][H]>[Pd].C(O)(=O)C>[CH:16]([NH:8][CH2:7][C:4]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([CH:4]3[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]3)[NH:8][C:9]=2[CH:15]=1)([CH3:5])[CH3:3])=[O:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 2476342-(4-Pyridyl)benzimidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 14153046HCID 14153046, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3.0 g. of the 5-(2-formylaminomethyl)prop-2-yl)-2-(4-pyridinyl)-benzimidazole prepared in Example 2 are hydrogenated in 50 ml. methanol in the presence of 1 ml. glacial acetic acid and 1 g. 10% palladium on charcoal for 6 hours at 50° C. and 5 bar hydrogen pressure. The reaction mixture is filtered, the filtrate is evaporated in a vacuum, the residue is digested with ethyl acetate, filtered off with suction and the residue is dissolved in 40 ml. hot dimethylformamide and filtered. After cooling, the filtrate is mixed with the same amount of ethyl acetate. After crystallisation, the product is filtered off with suction and washed with ethyl acetate to give 1.8 g. (59% of theory) of the title compound as colourless crystals; m.p. 234°-237° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated in a vacuum
  3. filtrationfiltered off with suction
  4. dissolutionthe residue is dissolved in 40 ml
  5. filtrationhot dimethylformamide and filtered
  6. temperatureAfter cooling
  7. additionthe filtrate is mixed with the same amount of ethyl acetate
  8. customAfter crystallisation
  9. filtrationthe product is filtered off with suction
  10. washwashed with ethyl acetate
  11. customto give 1.8 g

Sources & evidence

ORD record
ord-dadc34620b5b476f8f2e8a58b30f4e45
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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