Acetic Acid → HCID 19911575, compound

HRID 1708914Notes

Reaction equation

HRID 1708914 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][NH:8]N1C=CC=CC1N.Cl.[Cl:17][CH2:18][C:19](=[NH:23])OCC.[C:24](O)(=O)[CH3:25]>>[Cl:17][CH2:18][C:19]1[N:8]([CH2:7][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[C:2]2=[N:1][CH:6]=[CH:24][CH:25]=[C:3]2[N:23]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 67896527HCID 67896527, compound

Product 1

HCID 19911575HCID 19911575, compoundYield 100%

Procedure

To a stirred solution of 3.6 parts of N-(2-pyrazinylmethyl)-1,2-pyridinediamine in 30 parts of acetic acid were added 4.24 parts of ethyl 2-chloroethanimidate monohydrochloride. The reaction mixture was stirred first for 21 hours at room temperature and then for a few minutes at 90° C. The whole was evaporated and the residue was taken up in water. The aqueous layer was treated with sodium carbonate and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.9 parts (100%) of 2-(chloromethyl)-3-(2-pyrazinylmethyl)-3H-imidazo[4,5-b]pyridine as a residue (int. 29).

Workup

  1. waitfor a few minutes at 90° C
  2. customThe whole was evaporated
  3. additionThe aqueous layer was treated with sodium carbonate
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-48ad91c2c9244660bd49a55811cfdff7
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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