Pyrrolidine → HCID 58790077, compound

HRID 418609Notes

Reaction equation

HRID 418609 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[CH:5][CH:4]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CC(O)C>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:8][CH:7]=3)[S:17][C:16]=12

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 594245202-(4-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 58790077HCID 58790077, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 52 (444 mg, 0.98 mmol, crude material from the previous step) in iPrOH (10 ml) was added pyrrolidine (210 mg, 2.96 mmol) and the reaction mixture was refluxed for 4 hrs. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The solution was washed with water and the organic layer was collected, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated and the resultant oil was purified by column chromatography (eluents EtOAc to 30% MeOH in EtOAc), to afford title compound 53 (200 mg, 45% yield) as an orange solid. MS (m/z): 450.2 (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hrs
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe solution was washed with water
  5. customthe organic layer was collected
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe resultant oil was purified by column chromatography (eluents EtOAc to 30% MeOH in EtOAc)

Sources & evidence

ORD record
ord-3ded23a015c641e381cc2811f3216666
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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