Potassium Iodide → HCID 13769740, compound

HRID 979929Notes

Reaction equation

HRID 979929 reaction equation
Cl[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:29]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=[C:21]2[NH:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH:11][C:2]3[N:6]([CH3:7])[CH:5]=[N:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH2:15][CH2:16]2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 210101-Methyl-5-chloro-4-nitroimidazoleHCID 13588034HCID 13588034, compound

Product 1

HCID 13769740HCID 13769740, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.62 parts of 5-chloro-1-methyl-4-nitro-1H-imidazole, 3.67 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine, 1.1 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was cooled and poured onto water. 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, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.2 parts (45%) of 3-[(4-fluorophenyl)methyl]-N-[1-[2-[(1-methyl-4-nitro-1H-imidazol-5-yl)amino]ethyl]-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine; mp. 198.7° C. (compound 11 ).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. extractionThe product was extracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-f5f5de2a839642bc84dc31a6ccd887a9
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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