HCID 58466125, compound → HCID 58466146, compound

HRID 335778Notes

Reaction equation

HRID 335778 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:10]=3)[C@@:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:4]=2[CH:3]=1.[C:27]([Cu])#[N:28]>CN1C(=O)CCC1>[NH2:26][C:23]1[O:24][CH2:25][C@@:5]2([N:22]=1)[C:4]1[CH:3]=[C:2]([C:27]#[N:28])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([O:16][CH2:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 58466125HCID 58466125, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58466146HCID 58466146, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

(S)-2′-bromo-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (250 mg, 0.599 mmol) and CuCN (268 mg, 3.00 mmol) were brought up in NMP (1997 μL) and heated to 200° C. in the microwave. The reactions were cooled to rt, filtered and purified by reverse-phase preparative HPLC using a Gemini NX c!8 column (150*30 mm, 5 um), 0.1% TFA in CH3CN/H2O, gradient 0% to 70% over 10 min to provide the product. Solvent was removed by evaporation and the product was brought up in sat's aqueous NaHCO3 and DCM and extracted with DCM. The organic washes were combined, dried over Na2SO4, filtered and concentrated to give (R)-2-amino-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthene]-2′-carbonitrile.

Workup

  1. temperatureThe reactions were cooled to rt
  2. filtrationfiltered
  3. custompurified by reverse-phase preparative HPLC
  4. customover 10 min
  5. customto provide the product
  6. customSolvent was removed by evaporation
  7. extractionextracted with DCM
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3ce518c275f84d22b715ebb5b4e97bb5
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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