Iodoacetamide → HCID 14013412, compound

HRID 2309634Notes

Reaction equation

HRID 2309634 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-74bb2091e17248e397e96f6263b47da0
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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