Hydrochloric Acid → HCID 131716501, compound

HRID 1533970Notes

Reaction equation

HRID 1533970 reaction equation
C(O)(=O)/C=[CH:3]/[C:4]([OH:6])=[O:5].CC1[O:14]C(CN2C3=NC=CC=C3N=C2CN2CCN(C)CC2)=CC=1.I.CO[CH:36](OC)[CH2:37][NH:38][C:39]([NH:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]2[N:59]([CH2:60][CH2:61][O:62][CH2:63][CH3:64])[C:54]3=[N:55][CH:56]=[CH:57][CH:58]=[C:53]3[N:52]=2)[CH2:46][CH2:45]1)=[NH:40].Cl.[OH-:68].[Na+]>>[C:4]([OH:6])(=[O:5])[C:3]([OH:14])=[O:68].[CH2:63]([O:62][CH2:61][CH2:60][N:59]1[C:54]2=[N:55][CH:56]=[CH:57][CH:58]=[C:53]2[N:52]=[C:51]1[CH2:50][N:47]1[CH2:46][CH2:45][N:44]([CH2:43][CH2:42][NH:41][C:39]2[NH:40][CH:36]=[CH:37][N:38]=2)[CH2:49][CH2:48]1)[CH3:64]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131716502HCID 131716502, compoundHCID 178467911HCID 178467911, compound

Product 1

HCID 131716501HCID 131716501, compoundYield 3.7%

Procedure

A mixture of 14 parts of N-(2,2-dimethoxyethyl)-N'-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]guanidine monohydroiodide and 140 parts of a hydrochloric acid solution 1N was stirred for 48 hours at room temperature. The mixture was treated with a sodium hydroxide solution and the product was extracted with dichloromethane. The extract 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 (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was refluxed with methylbenzene and 4-methylbenzenesulfonic acid. The whole was evaporated and the residue was taken up in water and dichloromethane. The mixture was treated with a sodium hydroxide solution and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was further purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (90:10 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 dried, yielding 0.65 parts (3.7%) of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-N-(1H-imidazol-2-yl)-1-piperazineethanamine ethanedioate(1:2); mp. 170.5° C. (compound 124).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract 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. temperatureThe residue was refluxed with methylbenzene and 4-methylbenzenesulfonic acid
  10. customThe whole was evaporated
  11. additionThe mixture was treated with a sodium hydroxide solution
  12. customthe layers were separated
  13. customThe organic layer was dried
  14. filtrationfiltered
  15. customevaporated
  16. customThe residue was further purified by column chromatography over silica gel using
  17. additiona mixture of dichloromethane and methanol (90:10 by volume) as eluent
  18. customThe pure fractions were collected
  19. customthe eluent was evaporated
  20. filtrationThe salt was filtered off
  21. customdried

Sources & evidence

ORD record
ord-e0c1ebe436ad4b12a6b88f3e4f036bbb
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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