Trifluoroacetic acid → HCID 18771578, compound

HRID 479712Notes

Reaction equation

HRID 479712 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]([NH:26][C:27]3[N:28]=[C:29]([Br:32])[S:30][CH:31]=3)=[O:25])[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:32][C:29]1[S:30][CH:31]=[C:27]([NH:26][C:24]([NH:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH2:15][CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:18]=2)=[O:25])[N:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59110524HCID 59110524, compound

Product 1

HCID 18771578HCID 18771578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(2-{6-[3-(2-bromo-thiazol-4-yl)-ureido]-pyridin-2-yloxy}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (285 mg, 0.54 mmol) in anhydrous CH2Cl2 (6 mL) at RT, under N2, TFA (1.5 mL) was added. After 1.5 h the solvent was evaporated in vacuo. The residue was carefully treated with a saturated solution of NaHCO3 (aq) (10 mL), the precipitate was filtered off, washed with Et2O (3×5 mL) and dried in a vacuum oven at 60° C. for 5 h to yield the title compound as a white amorphous solid. MS m/z: 426.2, 428.2 (M+H). Calc'd. for C16H20BrN5O2S-426.33.

Workup

  1. customAfter 1.5 h the solvent was evaporated in vacuo
  2. additionThe residue was carefully treated with a saturated solution of NaHCO3 (aq) (10 mL)
  3. filtrationthe precipitate was filtered off
  4. washwashed with Et2O (3×5 mL)
  5. customdried in a vacuum oven at 60° C. for 5 h

Sources & evidence

ORD record
ord-56413f66e9164b93a4334de24fef5eed
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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