Ethanimidic acid, ethyl ester, hydrochloride (1:1) → N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amine

HRID 893701Notes

Reaction equation

HRID 893701 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][C:35]3[N:40]=[C:39]([NH2:41])[C:38](N)=[CH:37][CH:36]=3)[CH2:28][CH2:27]2)=[CH:11][CH:10]=1>C(O)(=O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][C:35]3[N:40]=[C:39]4[N:41]=[C:2]([CH3:3])[NH:7][C:38]4=[CH:37][CH:36]=3)[CH2:28][CH2:27]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 14989867N6-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-amino]-1-piperidinyl]ethyl]-2,3,6-pyridinetriamine

Product 1

HCID 13983131N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amineYield 48.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5 parts of ethyl ethanimidate hydrochloride, 9 parts of N6 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2,3,6-pyridinetriamine and 100 parts of acetic acid was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was dissolved in trichloromethane. Water was added and sodium hydrogen carbonate was added till foaming had ceased. 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, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 4.8 parts (48.5%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amine; mp. 202.0° C. (compound 146).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in trichloromethane
  3. additionWater was added
  4. additionsodium hydrogen carbonate was added
  5. customThe layers were separated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 2-propanone
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-51c230e8277141619dad61d96529575f
Source dataset
uspto-grants-1992_06
Patent number
US05126339

Reaction notes

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