HCID 131733477, compound → HCID 90426712, compound

HRID 2279052Notes

Reaction equation

HRID 2279052 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([NH:22][C:23]([N:25]3[CH2:29][CH2:28][N:27]([CH:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:26]3=[O:36])=[O:24])=[CH:17][C:16]=2[Cl:37])[CH:11]=[CH:10][N:9]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[C:16]([Cl:37])=[CH:17][C:18]([NH:22][C:23]([N:25]3[CH2:29][CH2:28][N:27]([CH:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[C:26]3=[O:36])=[O:24])=[C:19]([F:21])[CH:20]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 1

HCID 131733477HCID 131733477, compound

Product 1

HCID 90426712HCID 90426712, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl(4-(2-chloro-5-fluoro-4-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamido)phenoxy)pyridin-2-yl)carbamate (1.32 g, 2.400 mmol) was combined with TFA (20 mL), stirred at RT overnight and concentrated to dryness. The residue was treated with DCM, sonicated, the solid removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford N-(4-((2-aminopyridin-4-yl)oxy)-5-chloro-2-fluorophenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (382 mg, 35%). MS (ESI) m/z: (M+H+): 450.1.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with DCM
  3. customsonicated
  4. customthe solid removed via filtration
  5. concentrationthe filtrate concentrated to dryness
  6. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-8704cb5e37134c7a8783959fbc87f9a8
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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