Hydrochloric Acid → HCID 54534293, compound

HRID 1416976Notes

Reaction equation

HRID 1416976 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:7][C:8]1[C:13]([CH:14]=O)=[CH:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6].Cl>CO>[CH2:3]([O:7][C:8]1[C:13]([CH2:14][NH:2][CH3:1])=[CH:12][C:11]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)=[C:10]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 57299675HCID 57299675, compound

Product 1

HCID 54534293HCID 54534293, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine (2.0M in methanol, 1 ml) was added to a stirring mixture of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carboxaldehyde [Example 30] (150 mg, 0.35 mMol) and molecular sieves (3A, 1.0 g) in 50 ml methanol. After stirring for 4 hours, the mixture was cooled by an ice bath and 5 ml 5% HCl was added. The mixture was concentrated to an oil containing the molecular sieves. Water (50 ml) and 5 ml 5% NaHCO3 were added and the product was extracted into ethyl acetate (2×50 ml). The ethyl acetate extracts were combined, dried over Na2SO4, filtered and concentrated to a solid. The titled material was purified by silica gel chromatography to give a solid: m.p. (DSC) 113.98° C. Anal. Calc'd. C24H27N2O3SF: C, 65.14; H. 6.15; N, 6.33. Found: C, 64.81; H, 6.15; N, 6.17.

Workup

  1. temperaturethe mixture was cooled by an ice bath
  2. concentrationThe mixture was concentrated to an oil
  3. additioncontaining the molecular sieves
  4. additionWater (50 ml) and 5 ml 5% NaHCO3 were added
  5. extractionthe product was extracted into ethyl acetate (2×50 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customThe titled material was purified by silica gel chromatography
  10. customto give a solid

Sources & evidence

ORD record
ord-780cfc167e5d4af18d10caa6aa031914
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

Loading…