Potassium Iodide → HCID 86744563, compound

HRID 1886413Notes

Reaction equation

HRID 1886413 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:5](=[O:14])[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1.[CH3:15][C:16]1[O:20][C:19]([CH2:21][N:22]2[C:26]3=[N:27][CH:28]=[CH:29][CH:30]=[C:25]3[N:24]=[C:23]2[NH:31][CH:32]2[CH2:36][CH2:35][NH:34][CH2:33]2)=[CH:18][CH:17]=1.[C:37](=[O:40])([O-:39])O.[Na+].[I-].[K+]>C(O)C>[C:5]([OH:14])(=[O:6])/[CH:4]=[CH:3]/[C:37]([OH:39])=[O:40].[CH3:15][C:16]1[O:20][C:19]([CH2:21][N:22]2[C:26]3=[N:27][CH:28]=[CH:29][CH:30]=[C:25]3[N:24]=[C:23]2[NH:31][CH:32]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][C:4]3[C:5](=[O:14])[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[CH:9]=3)[CH2:33]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 2641213-(2-Bromoethyl)-2H-1-benzopyran-2-oneHCID 516892Sodium BicarbonateHCID 15037374HCID 15037374, compound

Product 1

HCID 86744563HCID 86744563, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.6 parts of 3-(2-bromoethyl)-2H-1-benzopyran-2-one, 6.0 parts of 3-[(5-methyl-2-furanyl)methyl]-N-(3-pyrrolidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 8.4 parts of sodium hydrogen carbonate, 0.1 parts of potassium iodide and 160 parts of ethanol was stirred for 4 hours at reflux temperature. After cooling to room temperature, the precipitated product was filtered off and the filtrate was evaporated. The residue was stirred in ethyl acetate. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, hexane, methanol and ammonium hydroxide (45:45:9:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in 2-propanone. The salt was filtered off and crystallized twice from ethanol. The product was filtered off, washed with ethanol and dried in vacuo at 50° C., yielding 3 parts (25.6%) of 3-[ 2-[3-[[3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-pyrrolidinyl]ethyl]-2H-1-benzopyran-2-one (E)-2-butenedioate(1:1); mp. 194.2° C. (compound 130).

Workup

  1. temperatureat reflux temperature
  2. filtrationthe precipitated product was filtered off
  3. customthe filtrate was evaporated
  4. stirringThe residue was stirred in ethyl acetate
  5. filtrationThe precipitate was filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane, hexane, methanol and ammonium hydroxide (45:45:9:1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customcrystallized twice from ethanol
  13. filtrationThe product was filtered off
  14. washwashed with ethanol
  15. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-dc1812c05b92446fb0269001a6eb407f
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

Loading…