Water → HCID 131716479, compound

HRID 2166144Notes

Reaction equation

HRID 2166144 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.[NH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:35]2[N:43]([CH2:44][CH2:45][O:46][CH2:47][CH3:48])[C:38]3=[N:39][CH:40]=[CH:41][CH:42]=[C:37]3[N:36]=2)[CH2:30][CH2:29]1.[OH2:49]>ClCCl>[C:6]([OH:8])(=[O:7])[C:3]([OH:46])=[O:49].[CH2:47]([O:46][CH2:45][CH2:44][N:43]1[C:38]2=[N:39][CH:40]=[CH:41][CH:42]=[C:37]2[N:36]=[C:35]1[NH:34][CH:31]1[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][NH:25][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:8])[CH2:29][CH2:30]1)[CH3:48]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 102683-Furoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 15718930HCID 15718930, compound

Product 1

HCID 131716479HCID 131716479, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 1.12 parts of 3-furancarboxylic acid, 2.02 parts of N,N-diethylethanamine and 195 parts of dichloromethane were added 2.6 parts of 2-chloro-1-methylpyridinium iodide at room temperature. After stirring for 1 hour, 3.3 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-amine were added and stirred overnight at room temperature. The 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 trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol. The salt was filtered off and dried, yielding 2.19 parts (36.1%) of N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinyl]ethyl]-3-furancarboxamide ethanedioate(1:2); mp. 160.7° C. (compound 142).

Workup

  1. stirringstirred overnight at room temperature
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. filtrationThe salt was filtered off
  11. customdried

Sources & evidence

ORD record
ord-9ee049fd0d1d4c99a27f626131de7824
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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