Water → N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-3-furancarboxamide ethanedioate

HRID 1708924Notes

Reaction equation

HRID 1708924 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.[CH2:25]([O:27][CH2:28][CH2:29][N:30]1[C:34]2=[N:35][CH:36]=[CH:37][CH:38]=[C:33]2[N:32]=[C:31]1[CH2:39][N:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][NH2:48])[CH2:42][CH2:41]1)[CH3:26].[OH2:49]>ClCCl>[C:6]([OH:8])(=[O:7])[C:3]([OH:27])=[O:49].[CH2:25]([O:27][CH2:28][CH2:29][N:30]1[C:34]2=[N:35][CH:36]=[CH:37][CH:38]=[C:33]2[N:32]=[C:31]1[CH2:39][N:40]1[CH2:41][CH2:42][N:43]([CH2:46][CH2:47][NH:48][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:8])[CH2:44][CH2:45]1)[CH3:26]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 102683-Furoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 199115154-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine

Product 1

HCID 131716500N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-3-furancarboxamide ethanedioateYield 39.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 1.12 parts of 3-furancarboxylic acid, 2 parts of N,N-diethylethanamine and 195 parts of dichloromethane were added 2.6 parts of 2-chloro-1-methylpyridinium iodide. After stirring for 1 hour at room temperature, 3.6 parts of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazine-ethanamine and the mixture was stirred for 6 hours at room temperature. The reaction mixture was poured into water and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 2-propanol. The salt was filtered off and crystallized from acetonitrile. The product was filtered off and dried, yielding 2.4 parts (39.6%) of N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-3-furancarboxamide ethanedioate(1:2); 132.2° C. (compound 110).

Workup

  1. customthe layers were separated
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of dichloromethane and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customcrystallized from acetonitrile
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-1aaa15b8b6ab4343bf4af8aacb701eac
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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