Sodium Carbonate → 3-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate

HRID 2166135Notes

Reaction equation

HRID 2166135 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[CH2:7]([O:9][CH2:10][CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:8].[C:28](=[O:31])([O-:30])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:5]([OH:4])(=[O:9])[C:28]([OH:30])=[O:31].[CH2:7]([O:9][CH2:10][CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][O:4][CH2:5][CH3:6])[CH2:26][CH2:27]1)[CH3:8]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 31374DimethylacetamideHCID 157188163-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine

Product 1

HCID 1317164753-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioateYield 12.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.08 parts of 1-chloro-2-ethoxyethane, 2.9 parts of 3-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 1.06 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 70° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by filtration 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 methanol. The salt was filtered off and dried, yielding 0.7 parts (12.9%) of 3-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate(1:2); mp. 176.1° C. (compound 44).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe residue was purified by filtration over silica gel using
  6. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-ca4a2b26daee4154b151275ace681bd8
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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