Hydrochloric Acid → HCID 67236381, compound

HRID 2364798Notes

Reaction equation

HRID 2364798 reaction equation
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.Cl>CN(C=O)C>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH:6]2[CH2:7][CH2:8][CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[N:36]2[C:35]2[CH:37]=[CH:38][C:32]([F:31])=[CH:33][CH:34]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 58226750HCID 58226750, compound

Product 1

HCID 67236381HCID 67236381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved the product from Example 39C (5.25 g, 10.05 mmol) in DMF (31 mL) and then added 4-fluoroaniline (9.65 mL, 101 mmol) and heated solution at 50° C. for 18 h. Solution was cooled to room temperature and 1N aq. HCl added (100 mL) then extracted with ethyl acetate (2×200 mL), then combined organic extracts washed with brine, dried and concentrated to an amber oil to which methanol (10 mL) was added and after 3 h a yellow solid (1.05 g, 24%) resulted as the title compound as a 1/1 mixture of trans pyrrolidine isomers.

Workup

  1. extractionthen extracted with ethyl acetate (2×200 mL)
  2. washcombined organic extracts washed with brine
  3. customdried
  4. concentrationconcentrated to an amber oil to which methanol (10 mL)
  5. additionwas added and after 3 h a yellow solid (1.05 g, 24%)

Sources & evidence

ORD record
ord-6a0acb00c3e54b81b1a0a0ef806dfcab
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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