Iodoacetamide → HCID 14013412, compound

HRID 1904838Notes

Reaction equation

HRID 1904838 reaction equation
I[CH2:2][C:3]([NH2:5])=[O:4].Cl.Cl.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:2][C:3]([NH2:5])=[O:4])[CH2:28][CH2:27]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 516892Sodium BicarbonateHCID 20037917HCID 20037917, compound

Product 1

HCID 14013412HCID 14013412, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.3 parts of 2-iodoacetamide, 20.0 parts of 3-[(4-fluorophenylmethyl]-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine dihydrochloride, 17.0 parts of sodium hydrogen carbonate and 200 parts of ethanol was stirred for 3 hours at at reflux temperature. The salts were filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:9:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone. The product was filtered off and dried in vacuo at 60° C., yielding 8.5 parts (44.5%) of 4-[[3-[(4-fluorophenyl)-methyl]-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineacetamide; mp. 153.4° C. (148).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe salts were filtered off
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:9:1 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone
  9. filtrationThe product was filtered off
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ce48a8d18bd349e2a3f99a1486707f1c
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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