Trifluoroacetic acid → HCID 68983071, compound

HRID 748628Notes

Reaction equation

HRID 748628 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[C:18]([NH:20][C:21]([NH:23][C:24]3[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[O:22])[CH:17]=[C:16]([F:31])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:31][C:16]1[CH:17]=[C:18]([NH:20][C:21]([NH:23][C:24]2[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[O:22])[CH:19]=[C:14]([O:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68988707HCID 68988707, compound

Product 1

HCID 68983071HCID 68983071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6.5 g of 3-{3-fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-carboxylic acid tert-butyl ester was added 20 mL of a 1:1 mixture of trifluoroacetic acid and dichloromethane at room temperature and the resultant reaction mixture was stirred for 2 hours. The reaction mixture was concentrated. To the residue was added 5 mL of saturated brine solution and 1 N NaOH was added until a pH of 10 was observed. The mixture was extracted with ethyl acetate. The organics were dried with sodium sulfate, filtered, and concentrated to 1-[3-fluoro-5-(pyrrolidin-3-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea, a compound of Formula I, as an oil that was used directly in the subsequent reaction.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. additionTo the residue was added 5 mL of saturated brine solution and 1 N NaOH
  4. additionwas added until a pH of 10
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe organics were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to 1-[3-fluoro-5-(pyrrolidin-3-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea
  9. customa compound of Formula I, as an oil that was used directly in the subsequent reaction

Sources & evidence

ORD record
ord-3c67573956e74107be1ff3b3bbfaf492
Source dataset
uspto-grants-2008_07
Patent number
US07399866B2

Reaction notes

Loading…