Pyridine → HCID 86594306, compound

HRID 751141Notes

Reaction equation

HRID 751141 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:19])([F:18])[F:17])[C@@H:14]3[C:20](=O)[CH2:21][CH2:22][N:13]3[C:12]2=[O:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CC=CC=1.Cl.[NH2:32][OH:33]>CO.O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:17])([F:18])[F:19])[C@@H:14]3[C:20](=[N:32][OH:33])[CH2:21][CH2:22][N:13]3[C:12]2=[O:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 59754351HCID 59754351, compound

Product 1

HCID 86594306HCID 86594306, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To 68A (96.0 mg, 0.269 mmol) in MeOH (2.7 mL) and water (5 drops) was added pyridine (109 μL) and hydroxylamine hydrochloride (93.0 mg, 1.34 mmol) and the whole was stirred overnight at rt. The reaction was concentrated then diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated. The resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 60-100% solvent B (A=90% H2O—10% MeOH and B=10% H2O—90% MeOH) over 10 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide a solid which was re-purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 40-70% solvent B (A=90% H2O—10% CH3CN and B=10% H2O—90% CH3CN) over 12 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide the title compound (48.0 mg) as a white solid. MS: m/z 371 [M−H]−.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthen diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified via preparative HPLC (YMC ODS C-18, 30×100 mm
  8. washeluting with 60-100% solvent B (A=90% H2O—10% MeOH and B=10% H2O—90% MeOH) over 10 min
  9. customUV detection at 220 nm) to provide a solid which
  10. customwas re-purified via preparative HPLC (YMC ODS C-18, 30×100 mm
  11. washeluting with 40-70% solvent B (A=90% H2O—10% CH3CN and B=10% H2O—90% CH3CN) over 12 min

Sources & evidence

ORD record
ord-547aa8bf97e841b9ab6f5c99bdca67ab
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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