Ethanol → HCID 59772688, compound

HRID 646261Notes

Reaction equation

HRID 646261 reaction equation
[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=[O:28])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.[BH4-].[Na+].[CH2:33](O)C>>[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH2:27][O:28][CH3:33])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 15949563HCID 15949563, compound

Product 1

HCID 59772688HCID 59772688, compound

Procedure

A solution of 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-ethyl-1H-pyrrole-2-carbaldehyde in dry ethanol was treated with 2 equivalents of sodium borohydride at 0° C., allowed to come to room temperature, quenched with water and evaporated to dryness under reduced pressure. The resultant residue is dispersed in water and extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was dissolved in 0.5M methanolic HCl, stirred overnight and evaporated to dryness under reduced pressure. This residue was dissolved in chloroform, washed with dilute sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified using flash chromatography and was crystallized from ethylacetate/hexane to give the title compound as a solid, mp 154-157° C., identified by NMR and mass spectral analyses.

Workup

  1. customto come to room temperature
  2. customquenched with water
  3. customevaporated to dryness under reduced pressure
  4. additionThe resultant residue is dispersed in water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resultant residue was dissolved in 0.5M methanolic HCl
  9. customevaporated to dryness under reduced pressure
  10. dissolutionThis residue was dissolved in chloroform
  11. washwashed with dilute sodium bicarbonate
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customThe resultant residue was purified
  15. customwas crystallized from ethylacetate/hexane

Sources & evidence

ORD record
ord-55f0f259ae69446bb586b562e2f6b4e4
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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