Trifluoroacetic acid → HCID 18771873, compound

HRID 460266Notes

Reaction equation

HRID 460266 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[C:10]([NH:12][C:13](=[O:35])[NH:14][C:15]3[N:20]=[C:19]([O:21][CH2:22][CH:23]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]4)[CH:18]=[CH:17][CH:16]=3)[N:11]=2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[S:8][CH:9]=[C:10]([NH:12][C:13]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([O:21][CH2:22][CH:23]4[CH2:27][CH2:26][NH:25][CH2:24]4)[N:20]=3)=[O:35])[N:11]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18771843HCID 18771843, compound

Product 1

HCID 18771873HCID 18771873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of tert-butyl 3-{6-[3-(2-pyridin-4-yl-thiazol-4-yl)-ureido]-pyridin-2-yloxymethyl}-pyrrolidine-1-carboxylate (1.291 g, 2.603 mmol) in CH2Cl2 (25 mL) was added TFA (5 mL) under N2. The reaction mixture was heated to reflux for 3 h, then cooled to rt. Saturated NaHCO3 solution (40 mL) was added and the precipitate was washed with EtOAc (3×40 mL) and H2O (2×10 mL), filtered and dried under high vacuum to give a white solid. MS m/z: 397.0 (M+H). Calc'd. for C19H21N6O2S-397.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. washthe precipitate was washed with EtOAc (3×40 mL) and H2O (2×10 mL)
  4. filtrationfiltered
  5. customdried under high vacuum
  6. customto give a white solid

Sources & evidence

ORD record
ord-ad50d88c9b8f4d668cbd9e1031d2cbdd
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

Loading…