Trifluoroacetic acid → HCID 18771646, compound

HRID 479708Notes

Reaction equation

HRID 479708 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][C:26]2[N:27]=[C:28]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[S:29][CH:30]=2)=[O:24])[N:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>CO>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:16]1[N:17]=[C:18]([NH:22][C:23]([NH:25][C:26]2[N:27]=[C:28]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[S:29][CH:30]=2)=[O:24])[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24886507HCID 24886507, compound

Product 1

HCID 18771646HCID 18771646, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2-({6-[3-(2-Pyridin-4-yl-thiazol-4-yl)-ureido]-pyridin-2-ylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (52 mg, 0.102 mmol) in MeOH (10 mL) was treated with TFA (0.1 mL, 1.3 mmol). The resulting mixture was heated at 50° C. for 24 h. The reaction mixture was cooled to RT and neutralized to pH between 8-9. Solvent was removed. The residue was partitioned between H2O and CHCl3. The organic layer was washed with H2O, brine, dried over MgSO4, and concentrated to give a yellow solid. MS m/z: 410.2 (M+H). Calc'd. for C20H23N7OS-409.17.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customSolvent was removed
  3. customThe residue was partitioned between H2O and CHCl3
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-923290ff1a8440b3a1b66c31484b9e09
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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