Water → HCID 131733475, compound

HRID 2278977Notes

Reaction equation

HRID 2278977 reaction equation
C1C(=O)N(Cl)C(=O)C1.[CH:9](=[N:11][OH:12])[CH3:10].[C:13]([C:15]1[CH:20]=[C:19]([O:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:26][CH:27]=2)[CH:18]=[CH:17][N:16]=1)#[CH:14].O>CN(C=O)C>[CH3:10][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[N:26][CH:27]=3)[CH:18]=[CH:17][N:16]=2)[O:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7863AldoximeHCID 31398ChlorosuccinimideHCID 131733474HCID 131733474, compound

Product 1

HCID 131733475HCID 131733475, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of NCS (0.36 g, 2.70 mmol) in DMF (2 mL) was treated with acetaldoxime (0.16 g, 2.70 mmol), stirred at RT for 0.5 h, added to a solution of tert-butyl (5-((2-ethynylpyridin-4-yl)oxy)pyridin-2-yl)carbamate (0.28 g, 0.90 mmol) and TEA (2 mL) in DMF (2 mL) and heated at 60° C. for 2 h. The mixture was treated with water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford tert-butyl (5-((2-(3-methylisoxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamate (250 mg, 75%). MS (ESI) m/z: 369.1 (M+H+).

Workup

  1. temperatureheated at 60° C. for 2 h
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-ba5e808a2d104beea4c2d11cedb9e12a
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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