Acetic Acid → HCID 19911575, compound

HRID 1533955Notes

Reaction equation

HRID 1533955 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-db1a2b3cdfc447ed95fc7ac4025f816a
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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