Sodium Bicarbonate → 3-(2-ethoxyethyl)-N-[1-[2-(phenylsulfonyl)ethyl]-4-piperidinyl]-3H-imidazo-[4,5-b]pyridin-2-amine hemihydrate

HRID 2166137Notes

Reaction equation

HRID 2166137 reaction equation
Br[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH2:13]([O:15][CH2:16][CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[N:20]=[C:19]1[NH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH3:14].C(=O)([O-])O.[Na+]>C(O)C>[OH2:5].[CH2:13]([O:15][CH2:16][CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[N:20]=[C:19]1[NH:27][CH:28]1[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:32][CH2:33]1)[CH3:14].[CH2:13]([O:15][CH2:16][CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[N:20]=[C:19]1[NH:27][CH:28]1[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:32][CH2:33]1)[CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12518322(2-Bromoethanesulfonyl)benzeneHCID 157188163-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine

Product 1

HCID 1317164763-(2-ethoxyethyl)-N-[1-[2-(phenylsulfonyl)ethyl]-4-piperidinyl]-3H-imidazo-[4,5-b]pyridin-2-amine hemihydrateYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.7 parts of [(2-bromoethyl)sulfonyl]benzene, 4.34 parts of 3-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 2.5 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred for 2 hours at reflux temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was taken up in water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of tetrahydrofuran and 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.6 parts (37.1%) of 3-(2-ethoxyethyl)-N-[1-[2-(phenylsulfonyl)ethyl]-4-piperidinyl]-3H-imidazo-[4,5-b]pyridin-2-amine hemihydrate; mp. 101.9° C. (compound 99).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered over diatomaceous earth
  3. customthe filtrate was evaporated
  4. extractionthe product was extracted with 4-methyl-2-pentanone
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from a mixture of tetrahydrofuran and 2,2'-oxybispropane
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-7b88b261bbba48ddbe6d61fe88939003
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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