Hydrochloric Acid → HCID 22114894, compound

HRID 1276059Notes

Reaction equation

HRID 1276059 reaction equation
Br[C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]3[CH:24]=[CH:25][N:26]=[C:14]23)=[C:4]([F:27])[CH:3]=1.[Cu][C:29]#[N:30].Cl>[Fe](Cl)Cl.CS(C)=O>[C:29]([C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[N:15]3[CH:24]=[CH:25][N:26]=[C:14]23)=[C:4]([F:27])[CH:3]=1)#[N:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22114869HCID 22114869, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22114894HCID 22114894, compound

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 8-(4-bromo-2-fluoro-5-methylsulfonylaminophenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (3.0 g), copper(I) cyanide (0.86 g) and dimethyl sulfoxide (30 ml) was heated for 7 hours at 160° C. under nitrogen atmosphere. After cooled to room temperature, the mixture was added with iron(II) chloride (0.8 g) and 6N hydrochloric acid (1.5 ml), and then stirred for 30 minuets at room temperature. The reaction solution was poured into ice water, and the thus obtained solid was filtered off and washed with ethyl acetate. The solid was dissolved into acetonitrile and then a portion adjacent to the original point of the short column of silica gel was removed. The eluate was concentrated to such an extent that any crystal did not precipitate, added with alumina (5.0 g) for column chromatography and stirred for 15 minuets. The alumina was filtered off, washed with a small amount of acetonitrile and then eluted with an acetonitrile solution (30 ml) containing triethylamine (5%) and water (5%). The eluate was distilled off under reduced pressure and the residue was added with ethyl acetate (10 ml), water (20 ml) and 6N hydrochloric acid (10 drops), followed by stirring vigorously to obtain a solid, which was then filtered off. The thus obtained solid was washed with water and ethyl acetate, and dried to give the compound of interest (0.6 g) as a white solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe thus obtained solid was filtered off
  3. washwashed with ethyl acetate
  4. dissolutionThe solid was dissolved into acetonitrile
  5. customa portion adjacent to the original point of the short column of silica gel was removed
  6. concentrationThe eluate was concentrated to such an extent that any crystal
  7. additionadded with alumina (5.0 g) for column chromatography
  8. stirringstirred for 15 minuets
  9. filtrationThe alumina was filtered off
  10. washwashed with a small amount of acetonitrile
  11. washeluted with an acetonitrile solution (30 ml)
  12. additioncontaining triethylamine (5%) and water (5%)
  13. distillationThe eluate was distilled off under reduced pressure
  14. additionthe residue was added with ethyl acetate (10 ml), water (20 ml) and 6N hydrochloric acid (10 drops)
  15. stirringby stirring vigorously
  16. customto obtain a solid, which
  17. filtrationwas then filtered off
  18. washThe thus obtained solid was washed with water and ethyl acetate
  19. customdried
  20. customto give the compound of interest (0.6 g) as a white solid

Sources & evidence

ORD record
ord-3e57aa74d15f4473b4a662448df2938e
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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