Methyl Picolinimidate → HCID 178420192, compound

HRID 1723145Notes

Reaction equation

HRID 1723145 reaction equation
[N:1]1([CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](=N)OC>C(O)(=O)C>[N:1]1([CH:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]2[CH:12]=[CH:11][C:10]3[NH:13][C:27]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)=[N:14][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 152260Methyl PicolinimidateHCID 14990928HCID 14990928, compound

Product 1

HCID 178420192HCID 178420192, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred and cooled solution of 5.3 parts of 4-[(1H-imidazol-1-yl)phenylmethyl]-1,2-benzenediamine in 50 parts of acetic acid were added 3.3 parts of methyl 2-pyridinecarboximidate while still cooling. The whole was stirred for 8 hours at room temperature and then allowed to stand over weekend. The reaction mixture was evaporated. The residue was taken up in water and treated with activated charcoal. The whole was filtered and the filtrate was made alkaline with ammonium hydroxide. The product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was dried in vacuo for 24 hours at 50° C., yielding 2.8 parts (40%) of 5-[(1H-imidazol-1-yl)phenylmethyl]-2-(2-pyridinyl)-1H-benzimidazole; mp. 123.3° C. (compound 201).

Workup

  1. temperaturewhile still cooling
  2. stirringThe whole was stirred for 8 hours at room temperature
  3. waitto stand over weekend
  4. customThe reaction mixture was evaporated
  5. additiontreated with activated charcoal
  6. filtrationThe whole was filtered
  7. filtrationThe product was filtered off
  8. custompurified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was dried in vacuo for 24 hours at 50° C.

Sources & evidence

ORD record
ord-b9d9351b8cfc43d2b474a971e048c83b
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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