반응 #84053

ord-70027d3c3d4d42b3bc9f47f06148eaaa

반응 방정식

Nc1ccc2ncccc2c1
6-aminoquinoline
Cl.O=C(CC1CN2CCC1CC2)Oc1c(F)c(F)c(F)c(F)c1F
pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride
CN(C)C=O
DMF
Cl
hydrochloric acid
O=C([O-])[O-]
carbonate
Cl.O=C(CC1CN2CCC1CC2)Nc1ccc2cccnc2c1
title compound
Cl.O=C(CC1CN2CCC1CC2)Nc1ccc2cccnc2c1
2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.WAITAfter 1 h
  2. 2
    여과the polystyrene resin is filtered off
  3. 3
    세척washed with THF
  4. 4
    농축The combined filtrates are concentrated in vacuo
  5. 5
    기타the crude product is purified by preparative HPLC
  6. 6
    기타The hydrochloride is prepared
  7. 7
    workup.ADDITIONby mixing the product
  8. 8
    농축concentrating again
  9. 9
    기타Drying under high vacuum

실험 절차

90.3 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 51.6 mg (0.36 mmol) of 6-aminoquinoline and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 1 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and concentrating again. Drying under high vacuum results in 44 mg (50.2% of theory) of the title compound.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09433614B2uspto-grants-2016_09