반응 #566883

ord-0a36fe690e6a48c58cd8470402f0ff46

용매

반응 조건

온도
85°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Upon reaching 85° C.
  2. 2
    온도The reaction was maintained at this temperature for 2.25 h
  3. 3
    온도After cooling to RT the mixture
  4. 4
    세척then washed with a saturated solution of NH4Cl(aq) (40 ml)
  5. 5
    기타The organic layer was separated
  6. 6
    건조dried over MgSO4
  7. 7
    여과filtered
  8. 8
    농축concentrated under reduced pressure
  9. 9
    기타The residue was purified by flash chromatography on silica gel (3:1/2:1/1:1, EtOAc:acetone)

실험 절차

To a stirred suspension of 2-bromothiazole-4-carboxylic acid (5.13 g, 2 mmol) in anhydrous CH3CN (40 ml) at RT, under N2, TEA (3.80 ml, 27 mmol) and (PhO)2PON3 (5.90 ml, 27 mmol) were added. The resulting solution was heated to 85° C. Upon reaching 85° C., a solution of 6-(piperidylmethyl)-2-pyridylamine (4.74 g, 25 mmol) in anhydrous CH3CN (60 ml) was added. The reaction was maintained at this temperature for 2.25 h. After cooling to RT the mixture was diluted with CH2Cl2 (50 ml) then washed with a saturated solution of NH4Cl(aq) (40 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1/2:1/1:1, EtOAc:acetone) to yield the title compound as a pale yellow solid. MS m/z: 396 (M+H), 398 (M+3). Calc'd for C15H18BrN50S: 395.04.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06645990B2uspto-grants-2003_11